- Rh-Catalyzed Coupling of Acrylic/Benzoic Acids with α-Diazocarbonyl Compounds: An Alternative Route for α-Pyrones and Isocoumarins
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A coupling of acrylic acids/benzoic acids with α-diazocarbonyl compounds has been realized by a combined catalytic system of rhodium catalyst and Zn(OAc)2 additive. The presence of Zn(OAc)2 obviously accelerates the C(sp2)
- Hong, Chao,Liu, Zhanxiang,Yu, Shuling,Zhang, Yuhong
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supporting information
p. 815 - 820
(2022/02/07)
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- Amino-modified Merrifield resins as recyclable catalysts for the safe and sustainable preparation of functionalized α-diazo carbonyl compounds
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Amino-functionalized polystyrene polymers derived from Merrifield resins were prepared and characterized. These basic materials were successfully employed as heterogeneous catalysts in the diazo transfer reaction to 1,3-dicarbonyl compounds, furnishing the corresponding diazo compounds in good to excellent yields and in relatively short reaction times. In addition, the work-up and purification protocols are simple and do not generate large amounts of waste, which are important features in sustainable catalysis and environmentally benign processes. The feasibility of the recovery and reuse of the amino-modified catalysts was also verified, since they can be employed up to five times without appreciable loss of catalytic activity. This straightforward procedure can be readily scaled up to gram scale, enabling the wide application of this method. The synthetic potential was demonstrated through the two-step preparation of 2-amino-N-dodecylacetamide (ANDA), a small molecule of commercial relevance.
- Fantinel, Mariane,Valiati, Nayara,Moro, Pedro A.M.,Sá, Marcus M.
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- Rhodium(III)-catalyzed chemodivergent annulations between phenyloxazoles and diazos via C–H activation
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Acid-controlled, chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(III)-catalyzed C[sbnd]H activation. Diazo compounds act as a carbene precursor, and coupling occurs in one-pot process, where adipic acid and trimethylacetic acid promote chemodivergent cyclizations.
- Zhang, Xueguo,Wang, Peigen,Zhu, Liangwei,Chen, Baohua
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supporting information
p. 695 - 699
(2020/06/28)
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- INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND/OR TRYPTOPHAN 2,3-DIOXYGENASE
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The present invention relates to compounds of Formula (I) inhibiting indoleamine 2,3-dioxygenase (IDO) and/or tryptophan 2,3-dioxygenase (TDO) enzymes. Further, their synthesis and their use as medicaments in the treatment of inter alia cancer is disclose
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Page/Page column 67
(2021/01/29)
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- INHIBITORS OF HUMAN ATGL
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The present invention relates to novel inhibitors of adipose triglyceride lipase (ATGL) having an improved inhibitory activity against human ATGL (hATGL) as well as pharmaceutical compositions comprising these inhibitors, and their therapeutic use, particularly in the treatment or prevention of a lipid metabolism disorder, including, e.g., obesity, non-alcoholic fatty liver disease, type 2 diabetes, insulin resistance, glucose intolerance, hypertriglyceridemia, metabolic syndrome, cardiac and skeletal muscle steatosis, congenital generalized lipodystrophy, familial partial lipodystrophy, acquired lipodystrophy syndrome, atherosclerosis, or heart failure.
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Page/Page column 242-244
(2021/02/05)
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- Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water
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Ruthenium(II)-catalyzed ortho-C-H alkylation of naphthylamines with diazo compounds for the synthesis of 2,2-disubstituted π-extended 3-oxindoles has been developed. The method represents the first example of C-H alkylation via carbenoid insertion in wate
- Wang, Xiaogang,Zhang, Jin,He, Yuan,Chen, Di,Wang, Chao,Yang, Fangzhou,Wang, Weitao,Ma, Yangmin,Szostak, Michal
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supporting information
p. 5187 - 5192
(2020/07/15)
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- Oxazolinyl-Assisted Ru(II)-Catalyzed C?H Functionalization Based on Carbene Migratory Insertion: A One-Pot Three-Component Cascade Cyclization
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A rare, ruthenium-catalyzed, oxazolinlyl assisted C?H functionalization and three-component cascade cyclization for the synthesis of isoquinolinones via a metal-carbene migratory insertion is reported. The transformation is unique since it involves the fo
- Kumar, Gangam Srikanth,Khot, Nandkishor Prakash,Kapur, Manmohan
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supporting information
p. 73 - 78
(2018/12/11)
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- Rh(III)-catalyzed annulation of BOC-protected benzamides with diazo compounds: Approach to isocoumarins
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A mild rhodium-catalyzed annulation of Boc-protected benzamides with diazo compounds via C?C/C?O bond formation has been explored. In the presence of [Cp*RhCl2]2, AgSbF6 and Cs2CO3, Boc-protected benzamides can be effectively annulated to yield isocoumarins in 0.5–2 h.
- Dong, Guangyu,Li, Chunpu,Liu, Hong
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- Cycloaddition of α-Diazocarbonyl Compounds and N-Tosylaziridines: Synthesis of Polysubstituted 2 H-1,4-Oxazines through Synergetic Catalysis of AgOTf/Cu(OAc)2
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An impressive and new [3 + 3]-cycloaddition of α-diazocarbonyl compounds with N-tosylaziridines via synergetic catalysis of AgOTf and Cu(OAc)2 has been well described, which offers efficient access to highly substituted 2H-1,4-oxazine derivatives. A variety of α-diazocarbonyl compounds and N-tosylaziridines were compatible substrates with convenient operations under mild reaction conditions.
- Fang, Shangwen,Zhao, Yanwei,Li, Haiyan,Zheng, Yonggao,Lian, Pengcheng,Wan, Xiaobing
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supporting information
p. 2356 - 2359
(2019/03/29)
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- Rhodium(i)-catalyzed vinylation/[2 + 1] carbocyclization of 1,6-enynes with α-diazocarbonyl compounds
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A sequential Rh(i)-catalyzed vinylation/[2 + 1]carbocyclization between enynes and diazo compounds has been developed. This transformation features a wide range of enynes and acceptor/acceptor diazo compounds, providing easy access to versatile vinyl-substituted azabicyclo[3.1.0]hexanes having a broad tolerance to functional groups.
- Huang, Junmin,Hu, Xinwei,Chen, Fengjuan,Gui, Jiao,Zeng, Wei
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supporting information
p. 7042 - 7054
(2019/08/01)
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- Rh(III)-Catalyzed C-H Activation of Benzoylacetonitriles and Tandem Cyclization with Diazo Compounds to Substituted Benzo [de] chromenes
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Rh (III)-catalyzed C-H activation of benzoylacetonitriles in coupling with diazo compounds was developed to synthesize diversified substituted benzo[de]chromenes via a formal (4 + 2) cycloaddition with a diazo compound and subsequent tandem (4 + 2) cycloa
- Fang, Feifei,Zhang, Chunmei,Zhou, Chaofan,Li, Yazhou,Zhou, Yu,Liu, Hong
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supporting information
p. 1720 - 1724
(2018/04/14)
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- Rhodium(I)-Catalyzed Coupling-Cyclization of C=O Bonds with α-Diazoketones
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An unprecedented intermolecular nucleophilic attack of C=X bonds (X = O and S) on the rhodium(I)-carbenes has been developed. This transformation allows for the coupling-cyclization of aroylamides with α-diazoketones and provides concise access to 2,4,5-trisubstituted 1,3-oxazoles and 1,3-thiazoles with a broad tolerance of functional groups.
- Chen, Ziyang,Hu, Xinwei,Huang, Junmin,Zeng, Wei
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supporting information
p. 3980 - 3983
(2018/07/15)
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- Catalytic Enantioselective Cloke–Wilson Rearrangement
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Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor cyclopropane substrate by the
- Ortega, Alesandere,Manzano, Rubén,Uria, Uxue,Carrillo, Luisa,Reyes, Efraim,Tejero, Tomas,Merino, Pedro,Vicario, Jose L.
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supporting information
p. 8225 - 8229
(2018/06/29)
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- Rh(III)-Catalyzed Regio- and Chemoselective [4 + 1]-Annulation of Azoxy Compounds with Diazoesters for the Synthesis of 2H-Indazoles: Roles of the Azoxy Oxygen Atom
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A Rh(III)-catalyzed tandem C-H alkylation/intramolecular decarboxylative cyclization of azoxy compounds with diazoesters for the synthesis of 3-acyl-2H-indazoles is disclosed. The azoxy instead of the azo group enables a distinct approach for cyclative capture, leading to a [4 + 1]-annulation rather than a classic [4 + 2] manner. The azoxy oxygen atom is traceless after annulation, and further removal from the product is not required. This reaction features a complete regioselectivity for unsymmetrical azoxybenzenes and a compatibility of monoaryldiazene oxides.
- Long, Zhen,Wang, Zhigang,Zhou, Danni,Wan, Danyang,You, Jingsong
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supporting information
p. 2777 - 2780
(2017/06/07)
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- Iron-Catalyzed Annulation of 1,2-Diamines and Diazodicarbonyls for Diverse and Polyfunctionalized Quinoxalines, Pyrazines, and Benzoquinoxalines in Water
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A novel and facile iron-catalyzed tandem annulation of o-phenylenediamines and diazocarbonyls in water for the construction of polyfunctionalized quinoxalines has been developed. The key strategy includes the one-pot domino N?H insertion, cyclization, and
- Pandit, Rameshwar Prasad,Kim, Sung Hong,Lee, Yong Rok
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supporting information
p. 3586 - 3599
(2016/11/25)
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- Rh(iii)-catalyzed relay carbenoid functionalization of aromatic C-H bonds: Access to π-conjugated fused heteroarenes
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A novel Rh(iii)-catalyzed relay cross-coupling/cyclization cascade between arylketoimines and diazoesters is described. This transformation provides a concise access to unique π-conjugated 1-azaphenalenes (1-APLEs) via a double aryl Csp2-H bond
- Xie, Ying,Chen, Xun,Liu, Xin,Su, Shi-Jian,Li, Jianzhang,Zeng, Wei
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supporting information
p. 5856 - 5859
(2016/05/19)
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- Controllable Rh(III)-Catalyzed Annulation between Salicylaldehydes and Diazo Compounds: Divergent Synthesis of Chromones and Benzofurans
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A Rh(III)-catalyzed annulation between salicylaldehydes and diazo compounds with controllable chemoselectivity is described. AgNTf2 favored benzofurans via a tandem C-H activation/decarbonylation/annulation process, while AcOH led to chromones through a C-H activation/annulation pathway. The reaction exhibited good functional group tolerance and scalability. Moreover, only a single regioisomer of benzofuran was obtained due to the in situ decarbonylation orientation effect.
- Sun, Peng,Gao, Shang,Yang, Chi,Guo, Songjin,Lin, Aijun,Yao, Hequan
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supporting information
p. 6464 - 6467
(2016/12/23)
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- Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones
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Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.
- Wu, Youzhi,Sun, Peng,Zhang, Kaifan,Yang, Tie,Yao, Hequan,Lin, Aijun
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p. 2166 - 2173
(2016/03/15)
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- Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds
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A Rh(iii)-catalyzed cross-coupling/cyclization cascade of α-imino Csp3-H bonds with donor/acceptor α-acyl diazocarbonyl compounds has been developed. This novel transformation involves ligand-directed Csp3-H bond functionalization with carbenoids under the pyridine-chelation assistance, and offered an efficient access to synthetically versatile polysubstituted N-(2-pyridyl)pyrroles with a broad range of functional group tolerance.
- Chen, Xun,Xie, Ying,Xiao, Xinsheng,Li, Guoqiang,Deng, Yuanfu,Jiang, Huanfeng,Zeng, Wei
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supporting information
p. 15328 - 15331
(2015/10/20)
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- Synthesis of Heterocycle-fused Pyridine N-Oxides from Oximes and Diazo Compounds via RhIII-Catalyzed C-H Activation and Annulation
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A RhIII-catalyzed tandem C-H activation and C-N bond formation reaction between oximes and diazo compounds for the synthesis of heterocycle-fused pyridine N-oxides has been developed. The reaction exhibits good functional group tolerance and regioselectivity. After simple transformation, the 1-substituted, 1,3-disubstituted, 1,4-disubstituted and 1,3,4-trisubstituted heterocycle-fused pyridines were all obtained in high efficiency. Moreover, this strategy has also been expanded to the synthesis of a key intermediate for the construction of one potential anti-HIV agent.
- Sun, Peng,Wu, Youzhi,Yang, Tie,Wu, Xiaoming,Xu, Jinyi,Lin, Aijun,Yao, Hequan
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supporting information
p. 2469 - 2473
(2015/08/18)
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- Tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions
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A mild and convenient method for the condensation of ethyl diazoacetate (EDA) with aldehydes catalyzed by tert-BuOK under solvent-free conditions was developed. The corresponding α-diazo-β-hydroxy esters were further converted into β-ketoesters through palladium-catalyzed 1,2-hydrogen migration under neat conditions. The two-step transformation exemplifies a simple method for the efficient and green synthesis of β-ketoesters. The Royal Society of Chemistry 2013.
- Chen, Shufeng,Yuan, Fang,Zhao, Haiying,Li, Baoguo
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p. 12616 - 12620
(2013/08/23)
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- Design and optimization of pyrazinecarboxamide-based inhibitors of diacylglycerol acyltransferase 1 ((DGAT1) leading to a clinical candidate dimethylpyrazinecarboxamide phenylcyclohexylacetic acid (AZD7687)
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A new series of pyrazinecarboxamide DGAT1 inhibitors was designed to address the need for a candidate drug with good potency, selectivity, and physical and DMPK properties combined with a low predicted dose in man. Rational design and optimization of this series led to the discovery of compound 30 (AZD7687), which met the project objectives for potency, selectivity, in particular over ACAT1, solubility, and preclinical PK profiles. This compound showed the anticipated excellent pharmacokinetic properties in human volunteers.
- Barlind, Jonas G.,Bauer, Udo A.,Birch, Alan M.,Birtles, Susan,Buckett, Linda K.,Butlin, Roger J.,Davies, Robert D.M.,Eriksson, Jan W.,Hammond, Clare D.,Hovland, Ragnar,Johannesson, Petra,Johansson, Magnus J.,Kemmitt, Paul D.,Lindmark, Bo T.,Morentin Gutierrez, Pablo,Noeske, Tobias A.,Nordin, Andreas,O'Donnell, Charles J.,Petersson, Annika U.,Redzic, Alma,Turnbull, Andrew V.,Vinblad, Johanna
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supporting information
p. 10610 - 10629
(2013/02/23)
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- CARBAMOYL COMPOUNDS AS DGAT1 INHIBITORS 190
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DGAT-1 inhibitor compounds of formula (I), pharmaceutically-acceptable salts and pro- drugs thereof are described, together with pharmaceutical compositions, processes for making them and their use in treating, for example, obesity wherein, for example, Ring A is optionally substituted 2,6-pyrazindiyl; X is =O; Ring B is optionally substituted 1,4-phenylene; Y1 is a direct bond or -O-; Y2 is -(CH 2) r- wherein r is 2 or 3; n is 0 or n is 1 when Y1 is a direct bond between Ring B and Ring C and when Ring B is 1,4-phenylene and Ring C is (4-6C)cycloalkane; Ring C is optionally substituted (4-6C)cycloalkane, (7-10C)bicycloalkane, (8-12C)tricycloalkane, phenylene or pryidindiyl; L is a direct bond or -O-; p is 0, 1 or 2 and when p is 1 or 2 RA1 and RA2 are each independently hydrogen or (1-4C)alkyl; Z is carboxy or a mimic or bioisostere thereof.
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Page/Page column 72
(2009/07/25)
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- Synthesis of 1,2,4-triazines. XII. New synthesis of 1,2,4-triazines with a functional group in the 6-position
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6-Acyl- (15, 17) and 6-ethoxycarbonyl-5-substituted 1,2,4-triazines (11) were prepared by refluxing acylhydrazones (10, 14) or N,N-dimethylaminomethylenehydrazones (16) with ammonium acetate in acetic acid. NMR-studies confirmed the high regio selectivity
- Ohsumi,Neunhoeffer
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p. 651 - 662
(2007/10/02)
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