- Transition metal-free approach to azafluoranthene scaffolds by aldol condensation/[1+2+3] annulation tandem reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes
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A transition metal-free aldol condensation/[1+2+3] annulation reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes has been developed for the general synthesis of azafluoranthenes. This domino reaction enables successive formation of three new bonds and two rings from readily accessible starting materials in a single operation. Furthermore, this methodology can also be utilized to construct chromeno[4,3-c]pyridines and benzo[c][2,6]naphthyridines in moderate yields.
- Dong, Penghui,Majeed, Kashif,Wang, Lingna,Guo, Zijian,Zhou, Fengtao,Zhang, Qiuyu
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p. 4855 - 4858
(2021/05/25)
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- “On-water” reduction of α-keto amide by Hantzsch ester: A chemoselective catalyst- and additive-free way to α-hydroxy amide
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An efficient and practical method for chemoselective “on-water” reduction of α-keto amide by Hantzsch ester without using any catalysts and additives was developed. Control experiments indicated that the intramolecular hydrogen bond of α-keto amide was cr
- Fang, Zhong-Bing,Yu, Ru-Rong,Hao, Fei-Yue,Jin, Zheng-Neng,Liu, Gu-Yue,Dai, Guo-Liang,Yao, Wu-Bing,Wu, Jia-Shou
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supporting information
(2021/11/18)
-
- A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triazepines
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The base-induced formal [4+3] cycloaddition reaction of C,N-cyclic azomethine imines with aza-ortho-quinone methides, generated in situ, is reported. This protocol provided an efficient method for the synthesis of biologically important 1,2,4-triazepine derivatives, with a wide substrate scope and excellent functional-group tolerance, and it gives moderate to excellent yields under mild conditions. Several of the derivatives exhibited in vitro antitumor activities against the A2780 cell line in a screening of the cancer cell lines HCT-116, H2228, and A2780 by an MTT assay.
- Wang, Xinyue,Li, Zefei,Feng, Chang,Zhen, Qi,Guo, Mingzhang,Yao, Yaning,Zou, Xinyu,Wang, Pengfei,Hou, Yunlei,Gong, Ping
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p. 2090 - 2096
(2021/09/06)
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- Copper-Catalyzed (4+1) Cascade Annulation of Terminal Alkynes with 2-(Tosylmethyl)anilines: Synthesis of 2,3-Disubstituted Indoles
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A novel strategy based on Cu-catalyzed (4+1) cascade annulation of terminal alkynes as one-carbon synthons with 2-(tosylmethyl)anilines has been developed for the expeditious synthesis of 2,3-disubstituted indoles, in which in situ generations of aza-o-quinone methides and alkynyl-copper(I) species are involved. This annulation provides an effective method for the assembly of synthetically and structurally interesting 2,3-disubstituted indoles.
- Yan, Xu,Liu, Chun-Fang,An, Xian-Tao,Ge, Xiao-Min,Zhang, Qing,Pang, Lin-Han,Bao, Xu,Fan, Chun-An
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supporting information
p. 8905 - 8909
(2021/11/24)
-
- Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines
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In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.
- Chen, Yang-Bo,Sun, Zhou,Wang, Ze-Shu,Ye, Long-Wu,Zhang, Hao-Wen,Zhu, Chunyin
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p. 3636 - 3644
(2020/03/06)
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- Enantioselective Synthesis of Complex Fused Heterocycles through Chiral Phosphoric Acid Catalyzed Intramolecular Inverse-Electron-Demand Aza-Diels–Alder Reactions
-
A stable asymmetric intramolecular Povarov reaction has been established to provide an efficient method to access structurally diverse trans,trans-trisubstituted tetrahydrochromeno[4,3-b]quinolines in high stereoselectivities of up to >99:1 diastereomeric
- Jarrige, Lucie,Gandon, Vincent,Masson, Géraldine
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supporting information
p. 1406 - 1413
(2020/01/24)
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- Copper-catalyzed tandemcis-carbometallation/cyclization of imine-ynamides with arylboronic acids
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An efficient copper-catalyzed tandem regioselectivecis-carbometallation/cyclization of imine-ynamides with arylboronic acids has been developed. This method leads to a facile and practical synthesis of valuable 2,3-disubstituted indolines in moderate to e
- Wang, Hao-Ran,Huang, En-He,Luo, Chen,Luo, Wen-Feng,Xu, Yin,Qian, Peng-Cheng,Zhou, Jin-Mei,Ye, Long-Wu
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supporting information
p. 4832 - 4835
(2020/05/13)
-
- Palladium-Catalyzed Regioselective Syn-Chloropalladation-Olefin Insertion-Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines
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A palladium catalyzed cascade process involving syn-chloropalladation, intramolecular olefin insertion, and oxidative C-Cl bond formation reactions was demonstrated for the synthesis of dichlorinated tetrahydroquinolines in high yields (up to 93%). The N-propargyl arylamines having a tethered α,β-unsaturated carbonyl moiety underwent a regioselective syn-chloropalladation followed by a Heck-type reaction to deliver the tetrahydroquinoline scaffold. The rare insertion of the second chlorine atom was rationalized comprising a PdII/IV catalytic cycle and oxidative cleavage of the C-PdII bond.
- Vinoth, Perumal,Karuppasamy, Muthu,Vachan,Muthukrishnan, Isravel,Maheswari, C. Uma,Nagarajan, Subbiah,Pace, Vittorio,Roller, Alexander,Bhuvanesh, Nattamai,Sridharan, Vellaisamy
-
-
- Direct Access to 9-Chloro-1 H-benzo[ b]furo[3,4- e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade
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An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.
- Karuppasamy, Muthu,Vachan,Vinoth, Perumal,Muthukrishnan, Isravel,Nagarajan, Subbiah,Ielo, Laura,Pace, Vittorio,Banik, Subrata,Maheswari, C. Uma,Sridharan, Vellaisamy
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p. 5784 - 5788
(2019/08/26)
-
- Catalyst- and Additive-Free Chemoselective Transfer Hydrogenation of α-Keto Amides to α-Hydroxy Amides by Sodium Formate
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A catalyst- and additive-free chemoselective transfer hydrogenation of α-keto amides to α-hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram-scale synthesis and transformation of the resultant α-hydroxy amides into polysubstituted acetamides and 2-arylindole derivatives. Control experiments suggest that the NH group of α-keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.
- Hao, Feiyue,Gu, Zhenyu,Liu, Guyue,Yao, Wubing,Jiang, Huajiang,Wu, Jiashou
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p. 5985 - 5991
(2019/09/10)
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- Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
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Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
- Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.
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p. 4703 - 4708
(2019/06/27)
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- Asymmetric [4+2] cycloaddition of azlactones with dipolar copper–allenylidene intermediates for chiral 3,4-dhydroquinolin-2-one derivatives
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In this paper, a pybox-copper catalyzed enantioselective decarboxylative [4+2] cycloaddition reaction of ethynyl benzoxazinanones with azlactones has been developed, which provides optically active 3,4-dihydroquinolin-2-ones in high yields with good enantioselectivities and diastereoselectivities. In this transformation, the chiral dipolar copper–allenylidene intermediates are kinetically generated via decarboxylative ethynyl benzoxazinanones, followed by the attack of the enolate azlactones to form enantiomerically enriched 3,4-dihydroquinolin-2-one structures.
- Sun, Bing-Bing,Hu, Qing-Xian,Hu, Jia-Ming,Yu, Jie-Qiang,Jia, Jun,Wang, Xing-Wang
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p. 1967 - 1970
(2019/06/27)
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- A nickel(ii)-catalyzed asymmetric intramolecular Alder-ene reaction of 1,7-dienes
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A highly diastereo- and enantioselective intramolecular Alder-ene reaction with an alkene as the enophile has been developed by using a chiral N,N′-dioxide/nickel(ii) complex as the catalyst. This protocol provides a facile route towards the synthesis of diverse 3,4-disubstituted chroman, tetrahydroquinoline, piperidine and thiochroman derivatives in high yields with good to excellent diastereo- and enantioselectivities.
- Liu, Wen,Zhou, Pengfei,Lang, Jiawen,Dong, Shunxi,Liu, Xiaohua,Feng, Xiaoming
-
supporting information
p. 4479 - 4482
(2019/04/26)
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- A [4 + 3] Annulation Reaction of aza- o-Quinone Methides with Arylcarbohydrazonoyl Chlorides for Synthesis of 2,3-Dihydro-1 H-benzo[ e][1,2,4]triazepines
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An unprecedented [4 + 3] annulation reaction of aza-ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1H-benzo[e][1,2,4]triazepine.
- Guo, Zhenyan,Jia, Hao,Liu, Honglei,Wang, Qijun,Huang, Jiaxing,Guo, Hongchao
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p. 2939 - 2943
(2018/05/28)
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- Phosphine-Catalyzed Reaction between 2-Aminobenzaldehydes and Dialkyl Acetylenedicarboxylates: Synthesis of 1,2-Dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction
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A series of 1,2-dihydroquinolines were synthesized in good to excellent yields by reacting 2-aminobenzaldehyde derivatives and dialkyl acetylenedicarboxylates with catalytic amounts of phosphine. This reaction was rendered catalytic by the selective in situ phosphine oxide reduction with the use of phenylsilane. Furthermore, with the same starting materials and with an additional role of the reducing agent, a new olefination reaction was discovered. Hydrogen/deuterium (H/D) exchange experiments revealed the possible mechanism of this reaction.
- Han, Xu,Saleh, Nidal,Retailleau, Pascal,Voituriez, Arnaud
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p. 4584 - 4588
(2018/08/09)
-
- Structure-activity relationship of the cinnamamide family of antibiotic potentiators for methicillin-resistant: Staphylococcus aureus (MRSA)
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Methicillin-resistant Staphylococcus aureus (MRSA) is a global public health threat. MRSA has evolved a complex set of biochemical processes that mobilize the organism for inducible resistance on challenge by β-lactam antibiotics. Interfering pharmacologi
- Speri, Enrico,Fishovitz, Jennifer,Mobashery, Shahriar
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p. 2008 - 2016
(2019/01/04)
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- Iridium- and Rhodium-Catalyzed Directed C-H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents
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The C-H heteroarylation of benzaldehydes with indoles and pyrroles was realized using the benziodoxolone hypervalent iodine reagents indole- and pyrroleBX. Functionalization of the aldehyde C-H bond using either an o-hydroxy or amino directing group and catalyzed by an iridium or a rhodium complex allowed the synthesis of salicyloylindoles and (2-sulfonamino)benzoylindoles, respectively, with good to excellent yields (74-98%). This new transformation could be carried out under mild conditions (rt to 40 °C) and tolerated a broad range of functionalities, such as ethers, halogens, carbonyls, or nitro groups.
- Grenet, Erwann,Waser, Jér?me
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supporting information
p. 1473 - 1476
(2018/03/09)
-
- Divergence in Ynone Reactivity: Atypical Cyclization by 3,4-Difunctionalization versus Rare Bis(cyclization)
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Functionalized ynones can be activated by Tf2C=CH2, which was generated in situ, to form zwitterionic species. These species were trapped in an intramolecular fashion by several nucleophiles to generate two major types of triflones in a divergent manner. Through fine-tuning of the reaction temperature, bis(triflyl)-6-membered- or (triflyl)-5-membered-fused-heterocycles were achieved in reasonable yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments.
- Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos,Delgado-Martínez, Patricia
-
supporting information
p. 8186 - 8194
(2018/06/15)
-
- Silver-Catalyzed Radical Cascade Cyclization toward 1,5-/1,3-Dicarbonyl Heterocycles: An Atom-/Step-Economical Strategy Leading to Chromenopyridines and Isoxazole-/Pyrazole-Containing Chroman-4-Ones
-
A novel and convenient silver-catalyzed radical cascade cyclization toward a large variety of 1,5-/1,3-dicarbonyl heterocycles containing a chroman-4-one, indanone, or 2,3-dihydroquinolin-4(1H)-one moiety was developed, by reacting various 2-functionalized benzaldehydes, including 2-allyloxy benzaldehydes, 2-allyl benzaldehyde, and 2-N(Ts)CH2-CH CH2 substituted benzaldehyde, with 1,3-dicarbonyl compounds in the presence of AgNO3/K2S2O8 in one pot under mild reaction conditions. The newly obtained 1,5-/1,3-dicarbonyl-containing heterocycles were further used directly to synthesize more structurally diverse polyheterocycles, mainly including chromenopyridines as well as isoxazole- or pyrazole-containing chroman-4-ones.
- Hu, Hao,Chen, Xiaolan,Sun, Kai,Wang, Junchao,Liu, Yan,Liu, Hui,Fan, Lulu,Yu, Bing,Sun, Yuanqiang,Qu, Lingbo,Zhao, Yufen
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supporting information
p. 6157 - 6160
(2018/10/05)
-
- NOVEL BENZO [...] DERIVATIVES AND THEIR MEDICAL USE
-
One objective of the present invention is to provide a compound having V2 receptor agonist effect. The pharmaceutical composition of this invention uses a compound expressed by the following general formula (I) or its pharmacologically acceptable salt as an active ingredient, wherein, R1 represents the following formula: wherein, A represents a lower alkylene group or the like which may be substituted with a lower alkyl group; R6 represents a hydrogen atom or the like; R7 represents a hydroxyl group, an aromatic heterocyclic group which may be substituted with a lower alkyl group, amine methyl acyl or the like; R2 represents a hydrogen atom or a lower alkyl group; R3 represents a lower alkyl group which may be substituted with 1 to 3 fluorine atoms or a halogen atom; R4 represents 5-membered aromatic monocyclic heterocyclic group, or 5-membered non-aromatic monocyclic heterocyclic group or the like, wherein the heterocyclic group contains at least one nitrogen atom, and may be substituted with a lower alkyl group; R 5 represents a lower alkyl group or a halogen atom or the like.
- -
-
Page/Page column 32
(2019/04/26)
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- Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O2: a facile protocol to selectively synthesize 2- and 3-vinylindoles
-
A novel palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes using molecular oxygen as the terminal oxidant through β-carbon elimination of aminopalladation intermediates is disclosed. The reaction opens up an effective way to obtain a series of 2- and 3-vinylindoles which are important synthetic intermediates in many natural indole derivatives.
- Cao, Bo,Simaan, Marwan,Marek, Ilan,Wei, Yin,Shi, Min
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p. 216 - 219
(2016/12/27)
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- Pd(II)-catalyzed enantioselective intramolecular oxidative amination utilizing (+)-camphorsulfonic acid
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An enantioselective Pd(II)-catalyzed intramolecular oxidative amination reaction was developed utilizing the commercially available chiral X-type ligand (1S)-(+)-camphorsulfonic acid. The Wacker-type cyclization produced chiral indoline products with enantioselectivies up to 45% ee. Electronic structure calculations employing density functional theory support a trans-aminopalladation mechanism.
- Aebly, Andrew H.,Rainey, Trevor J.
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p. 3795 - 3799
(2017/09/15)
-
- Tandem [3 + 2] cycloaddition/1,4-addition reaction of azomethine ylides and aza-o-quinone methides for asymmetric synthesis of imidazolines
-
An enantioselective synthesis of biologically important imidazolidines has been achieved via a tandem [3 + 2] cycloaddition/1,4-addition reaction of azomethine ylide and aza-o-quinone methides. With the use of this tool, various imidazolidine derivatives are obtained in good yields with excellent diastereoselectivities and enantioselectivities.
- Jia, Hao,Liu, Honglei,Guo, Zhenyan,Huang, Jiaxing,Guo, Hongchao
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p. 5236 - 5239
(2017/11/06)
-
- Iron-Catalyzed Synthesis of α-Dienyl Five- and Six-Membered N-Heterocycles
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The iron-catalyzed synthesis of α-dienyl N-heterocycles is reported. The method is cost-effective, atom-economic, and led to a range of substituted α-dienyl heterocycles in moderate to good yields and diastereoselectivities. The α-dienyl piperidines are key synthetic intermediates as demonstrated by the preparation of a panel of α-polyenyl N-heterocycles.
- Gonnard, Laurine,Guérinot, Amandine,Cossy, Janine
-
supporting information
p. 6160 - 6167
(2017/11/15)
-
- Observations concerning the synthesis of heteroatom-containing 9-membered benzo-fused rings by ring-closing metathesis
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A set of benzo-fused dienes with a 1,9-relationship and containing a variety of nitrogen and oxygen heteroatoms was readily synthesized. These dienes were then treated with the Grubbs second generation catalyst with the aim of synthesizing the 9-membered benzannelated heterocycles containing two heteroatoms (either O,O, NR,NR or O,NR where R = Ts or Boc). As previously observed in the literature, many of the dienes did not give the expected ring-closed product. However, a number of the desired products did form, namely with the 1,2-dihydrobenzo[c][1,5]oxazonin-7(5H)-one, 5,7-dihydrobenzo[b][1,5]oxazonine-6(2H)-carboxylate and 2,5,6,7-tetrahydrobenzo[b][1,5]oxazonine cores, albeit in poor yields. Rather surprisingly, the N-allyl-N-(2-(N-allyl-4-methylphenylsulfonamido)benzyl)-4-methylbenzenesulfonamide scaffold gave the desired ring-closed 1,6-ditosyl-2,5,6,7-tetrahydro-1H-benzo[b][1,5]diazonine in a high yield. Furthermore, when treated with the catalyst [RuClH(CO)(PPh3)3] the alkene isomerized into conjugation only with the benzylic NTs group and not with the phenyl NTs group to afford the 1,6-ditosyl-2,3,6,7-tetrahydro-1H-benzo[b][1,5]diazonine structure.
- Aderibigbe, Blessing A.,Green, Ivan R.,Mabank, Tanya,Janse van Rensburg, Mari,Morgans, Garreth L.,Fernandes, Manuel A.,Michael, Joseph P.,van Otterlo, Willem A.L.
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p. 4671 - 4683
(2017/07/10)
-
- Synthesis of a novel methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene) sulfonamido]methyl}-3-(2-methoxyphenyl)prop-2-enoate: Molecular structure, spectral, antimicrobial, molecular docking and DFT computational approaches
-
The title compound methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene)sulfonamido] methyl}-3-(2-methoxyphenyl)prop-2-enoate (MFMSM) has been synthesized and single crystals were grown by slow evaporation solution growth technique at room temperature. XRD,
- Murugavel,Vetri velan,Kannan, Damodharan,Bakthadoss, Manickam
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p. 457 - 475
(2016/08/12)
-
- Palladium(II)-catalyzed aerobic intramolecular allylic C[sbnd]H activation for the synthesis of indolines
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A method for the preparation of indolines via palladium-catalyzed aerobic intramolecular allylic C[sbnd]H activation was developed. Oxygen was successfully used as oxidant with catalytic amount of 1,4-benzoquinone. 16 examples were reported, the majority of substrates gave moderate to good yields.
- Xu, Changrui,Wu, Zhengxing,Chen, Jianzhong,Xie, Fang,Zhang, Wanbin
-
supporting information
p. 1904 - 1910
(2017/03/11)
-
- Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Br?nsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles
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A novel route to 1,3-oxazaheterocycles based on cooperative Ru-H/Br?nsted acid catalysis is reported. The use of the commercially available RuH2(CO)(PPh3)3 complex allows for an efficient long distance chain-walking process while the Br?nsted acid is responsible for generation of an electrophilic iminium ion which is trapped intramolecularly by an alcohol moiety. The alcohol, besides its nucleophilic function, also plays an important role in the stabilization of the Ru catalyst. (Chemical Equation Presented).
- Bernárdez, Rodrigo,Suárez, Jaime,Fa?anás-Mastral, Martín,Varela, Jesús A.,Saá, Carlos
-
supporting information
p. 642 - 645
(2016/03/01)
-
- Synthesis, crystal structure analysis, spectral investigations, DFT computations, Biological activities and molecular docking of methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene) sulfonamido]methyl}-3-(4-fluorophenyl)prop-2-enoate, a potential bioactive
-
The title compound methyl(2E)-2-{[N-(2-formylphenyl) (4-methylbenzene)sulfonamido]methyl}-3-(4-fluorophenyl) prop-2-enoate (MFMSF) has been synthesized and single crystals were grown by slow evaporation solution growth technique at room temperature. The g
- Murugavel,Vetri Velan,Kannan, Damodharan,Bakthadoss, Manickam
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p. 150 - 167
(2015/12/24)
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- Experimental and computational approaches of a novel methyl (2E)-2-{[N-(2-formylphenyl)(4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl)prop-2-enoate: A potential antimicrobial agent and an inhibition of penicillin-binding protein
-
The title compound methyl(2E)-2-{[N-(2-formylphenyl) (4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl) prop-2-enoate (MFMSC) has been synthesized and single crystals were grown by slow evaporation solution growth technique at room temperature. Struc
- Murugavel,Vetri Velan,Kannan, Damodharan,Bakthadoss, Manickam
-
-
- Convergent synthesis of 2-aryl-substituted quinolines by gold-catalyzed cascade reaction
-
Gold-catalyzed auto-tandem catalysis has been developed for synthesizing 2-aryl-substituted quinolines. The reaction of an aniline bearing an acetal moiety with an aryl alkyne proceeded via formal [4+2]-cycloaddition, which involved the addition of gold acetylide to an oxonium ion to give amino alkyne intermediate and sequential 6-endo-dig cyclization of amino alkyne intermediate by attacking of nitrogen to alkyne moiety activated by gold catalyst. The cationic gold catalyst promoted two different processes by enhancing the nucleophilicity and electrophilicity of alkyne. This convergent synthetic methodology enabled the synthesis of a variety of 2-aryl-substituted quinolines.
- Ueda, Hirofumi,Yamaguchi, Minami,Tokuyama, Hidetoshi
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p. 824 - 829
(2016/07/14)
-
- The Synthesis of 5-Amino-dihydrobenzo[b]oxepines and 5-Amino-dihydrobenzo[b]azepines via Ichikawa Rearrangement and Ring-Closing Metathesis
-
The combination of Ichikawa's rearrangement and a ring-closing metathesis reaction of allyl carbamates is presented as a method for the preparation of 5-amino-substituted 2,5-dihydro-benzo[b]oxepines, 2,5-dihydro-benzo[b]azepines, and 2,5-dihydro-benzo[b]thiepins. It was demonstrated that the use of nonracemic allyl carbamates enables the synthesis of enantioenriched benzo-fused seven-membered heterocycles. Finally, it was shown that further functionalization of the obtained structures allows access to pharmacologically active 5-amino-substituted 2,3,4,5-tetrahydro-1-benzo[b]oxepine scaffolds.
- Chwastek, Monika,Pieczykolan, Micha?,Stecko, Sebastian
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p. 9046 - 9074
(2016/10/17)
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- One-Pot Relay Gold(I) and Br?nsted Acid Catalysis: Cyclopenta[b]annulation of Indoles via Hydroamination/Nazarov-Type Cyclization Cascade of Enynols
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An expedient relay gold(I) and Br?nsted acid catalyzed hydroamination/Nazarov cyclization of 1-(2-aminophenyl)pent-4-en-2-ynols for the synthesis of various polyfunctionalized cyclopenta[b]indoles is described. The synthetic utility of this method has bee
- Dhiman, Seema,Ramasastry
-
supporting information
p. 5116 - 5119
(2015/11/03)
-
- Synthesis of polysubstituted cyclopenta[b]indoles via relay gold(i)/Bronsted acid catalysis
-
An efficient relay catalytic process involving Au(i)/Bronsted acid to access various polysubstituted cyclopentannulated indoles from easily accessible 1-(2-aminophenyl)prop-2-ynols and readily available 1,3-dicarbonyls has been developed. In an unprecedented event, the intermediate 2-indolylmethyl cations undergo the cation-Ene reaction with various 1,3-dicarbonyls followed by an intramolecular Friedel-Crafts-type reaction generating functionalized cyclopenta[b]indoles. This journal is
- Dhiman, Seema,Ramasastry
-
p. 557 - 560
(2015/01/09)
-
- A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes
-
Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is
- Arai, Shigeru,Hori, Hiroto,Amako, Yuka,Nishida, Atsushi
-
supporting information
p. 7493 - 7496
(2015/05/04)
-
- NOVEL BENZOAZEPINE DERIVATIVE AND MEDICAL USE THEREOF
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A compound having a V2 receptor agonistic activity is provided. Providing a pharmaceutical composition which contains, as an active ingredient, a compound represented by general formula (I) described below: [R1 is formula described below: (A is a lower alkylene group which may be substituted with lower alkyl group; R6 is a hydrogen atom; R7 is a hydroxyl group, an aromatic heterocyclic group which may be substituted with lower alkyl group, carbamoyl group); R2 is a hydrogen atom or lower alkyl group; R3 is lower alkyl group which may be substituted with 1-3 fluorine atoms, or halogen atom; R4 is a five-membered aromatic monocyclic heterocyclic group, five-membered non-aromatic monocyclic heterocyclic group, (provided each heterocyclic groups contain at least one nitrogen atom and may be substituted with a lower alkyl group); and R5 is a lower alkyl group, halogen atom], or pharmacologically acceptable salt thereof.
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Paragraph 0129
(2015/11/18)
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- Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
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The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).
- Kim, Shinae,Kang, Ki-Tae,Kim, Sung-Gon
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p. 5114 - 5121
(2014/07/08)
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- Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
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The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).
- Kim, Shinae,Kang, Ki-Tae,Kim, Sung-Gon
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p. 5114 - 5121
(2014/12/10)
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- One-pot catalytic enantioselective synthesis of functionalized tetrahydroquinolines by aza-michael/michael cascade reactions of N-protected 2-aminophenyl α,β-unsaturated esters with Nitroolefins
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A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biological properties has been developed by means of asymmetric organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl α,β-unsaturated esters in the presence of a chiral thiourea catalyst. The reaction gave the corresponding highly functionalized tetrahydroquinolines in good yields, excellent diastereoselectivities (>30:1 dr), and high enantioselectivities (≤99% ee).
- Kang, Ki-Tae,Kim, Sung-Gon
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p. 3365 - 3373
(2015/01/09)
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- RhIII-catalyzed hydroacylation reactions between N-sulfonyl 2-aminobenzaldehydes and olefins
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Metal-catalyzed hydroacylation of olefins represents an important atom-economic synthetic process in C-H activation. For the first time highly efficient RhIIICp*-catalyzed hydroacylation was realized in the coupling of N-sulfonyl 2-aminobenzald
- Zhang, Tao,Qi, Zisong,Zhang, Xueyun,Wu, Lamei,Li, Xingwei
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supporting information
p. 3283 - 3287
(2014/04/03)
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- Rhodium(iii)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins through C-H activation
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Rh(iii)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins via C-H bond activation is described. Diarylketones were obtained through coupling of N-sulfonyl 2-aminobenzaldehydes with 7-oxabenzonorbornadienes. On the other
- Yang, Tingting,Zhang, Tao,Yang, Shangdong,Chen, Shanshan,Li, Xingwei
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supporting information
p. 4290 - 4294
(2014/06/23)
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- 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis
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A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. Copyright
- Kothandaraman, Prasath,Koh, Bing Qin,Limpanuparb, Taweetham,Hirao, Hajime,Chan, Philip Wai Hong
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supporting information
p. 1978 - 1985
(2013/03/14)
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- N-heterocyclic carbene-catalyzed enantioselective intramolecular N-tethered aldehyde-ketone benzoin reactions
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The N-heterocyclic carbene-catalyzed enantioselective intramolecular benzoin reaction of N-tethered substrates was realized. With 15 mol % of d-camphor-derived triazolium salt E and 10 mol % of NaOAc, the aldehyde-ketone cross benzoin reactions of various substituted N-tethered substrates proceeded smoothly to afford dihydroquinolinone derivatives with a quaternary carbon stereocenter in moderate to good yields and excellent ee.
- Jia, Min-Qiang,You, Shu-Li
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p. 622 - 624
(2013/05/09)
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- Iodine-mediated intramolecular amination of ketones: The synthesis of 2-acylindoles and 2-acylindolines by tuning N-protecting groups
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A general method for constructing both 2-acylindoles and 2-acylindolines via I2-mediated intramolecular C-N bond formation is presented, and the selective formation of either 2-acylindoles or 2-acylindolines just depends on the nitrogen protecting groups used in the same substrate skeletons. The Royal Society of Chemistry.
- Gao, Wen-Chao,Jiang, Shan,Wang, Ruo-Lin,Zhang, Chi
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supporting information
p. 4890 - 4892
(2013/07/05)
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- Broensted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans
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Broensted acid-catalyzed one-pot synthesis of indoles from o-aminobenzyl alcohols and furans has been developed. This method operates via the in situ formation of aminobenzylfuran, followed by its recyclization into the indole core. The method proved to be efficient for substrates possessing different functional groups, including -OMe, -CO2Cy, and -Br. The resulting indoles can easily be transformed into diverse scaffolds, including 2,3- and 1,2-fused indoles, and indoles possessing an α,β-unsaturated ketone moiety at the C-2 position.
- Kuznetsov, Alexey,Makarov, Anton,Rubtsov, Aleksandr E.,Butin, Alexander V.,Gevorgyan, Vladimir
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p. 12144 - 12153
(2014/01/06)
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- Preparation of functional benzofurans and indoles via chemoselective intramolecular Wittig reactions
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A general preparation of new types of benzofurans, benzothiophenes and indoles is realized via chemoselective intramolecular Wittig reactions with the corresponding ester, thioester and amide functionalities using in situ formed phosphorus ylides as key i
- Lee, Yu-Ting,Jang, Yeong-Jiunn,Syu, Siang-En,Chou, Shu-Chi,Lee, Chia-Jui,Lin, Wenwei
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supporting information; experimental part
p. 8135 - 8137
(2012/09/07)
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- Concise synthesis and anti-HIV activity of pyrimido[1,2-c][1,3] benzothiazin-6-imines and related tricyclic heterocycles
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3,4-Dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine (PD 404182) is a virucidal heterocyclic compound active against various viruses, including HCV, HIV, and simian immunodeficiency virus. Using facile synthetic approaches that we developed for the synthesis of pyrimido[1,2-c][1,3]benzothiazin-6-imines and related tricyclic derivatives, the parallel structural optimizations of the central 1,3-thiazin-2-imine core, the benzene part, and the cyclic amidine part of PD 404182 were investigated. Replacement of the 6-6-6 pyrimido[1,2-c][1,3] benzothiazin-6-imine framework with 5-6-6 or 6-6-5 derivatives led to a significant loss of anti-HIV activity, and introduction of a hydrophobic group at the 9- or 10-positions improved the potency. In addition, we demonstrated that the PD 404182 derivative exerts anti-HIV effects at an early stage of viral infection.
- Mizuhara, Tsukasa,Oishi, Shinya,Ohno, Hiroaki,Shimura, Kazuya,Matsuoka, Masao,Fujii, Nobutaka
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supporting information; experimental part
p. 6792 - 6802
(2012/09/22)
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- Pd(II)-catalyzed oxidative cyclization reaction for the preparation of 2-substituted 1,2,3,4-tetrahydroquinolines with halide functionality
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The first Pd(II)-catalyzed oxidative cyclization reaction was developed for preparation of 2-substituted 1,2,3,4-tetrahydroquinolines from olefinic tosylamides. Under the optimized conditions, up to 86% yield was obtained. This reaction provides direct an
- Jiang, Feng,Wu, Zhengxing,Zhang, Wanbin
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experimental part
p. 1501 - 1505
(2011/03/22)
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- Sulfonamide-imines as selective fluorescent chemosensors for the fluoride anion
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Two new sulfonamide-type fluorescent chemosensors in organic media are reported. The two receptors, [N,N′-bis(2-tosylaminobenzylidene)-1,2- diaminoethane and N,N′-bis(2-tosylaminobenzylidene)-1,3-diamino-2- propanol], display marked changes in the fluores
- Lopez, Miguel Vazquez,Bermejo, Manuel R.,Vazquez, M. Eugenio,Taglietti, Angelo,Zaragoza, Guillermo,Pedrido, Rosa,Martinez-Calvo, Miguel
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body text
p. 357 - 362
(2010/02/16)
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- Diphosphine-catalyzed mixed double-michael reaction: A unified synthesis of lndolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1- oxazines
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(Figure Presented) Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridlnes, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinuc
- Sriramurthy, Vardhineedi,Kwon, Ohyun
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supporting information; experimental part
p. 1084 - 1087
(2010/06/15)
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