- Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with ω-Amino Fatty Acids under Hydrosilylation Conditions
-
An efficient method for the preparation of lactams from ω-amino fatty acids under hydrosilylation is described. A variety of lactams such as pyrrolidinones, piperidinones and 2-azepanones were selectively synthesised in moderate to excellent yields (29 examples, up to 95 % isolated yields) with a good functional group tolerance. Notably, no metallic based catalyst was required to perform this transformation.
- Tongdee, Satawat,Wei, Duo,Wu, Jiajun,Netkaew, Chakkrit,Darcel, Christophe
-
supporting information
p. 5536 - 5539
(2021/08/07)
-
- Transition-Metal-Free Reductive Functionalization of Tertiary Carboxamides and Lactams for α-Branched Amine Synthesis
-
A new method for the synthesis of α-branched amines by reductive functionalization of tertiary carboxamides and lactams is described. The process relies on the efficient and controlled reduction of tertiary amides by a sodium hydride/sodium iodide composite, in situ treatment of the resulting anionic hemiaminal with trimethylsilyl chloride and subsequent coupling with nucleophilic reagents including Grignard reagents and tetrabutylammonium cyanide. The new method exhibits broad functional-group compatibility, operates under transition-metal-free reaction conditions, and is suitable for various synthetic applications on both sub-millimole and on multigram scales.
- Chiba, Shunsuke,Dixon, Darren J.,Fan, Dongyang,Ong, Derek Yiren
-
supporting information
p. 11903 - 11907
(2020/05/22)
-
- A Unified Strategy for the Synthesis of Difluoromethyl- And Vinylfluoride-Containing Scaffolds
-
Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.
- Duchemin, Nicolas,Buccafusca, Roberto,Daumas, Marc,Ferey, Vincent,Arseniyadis, Stellios
-
supporting information
p. 8205 - 8210
(2019/10/16)
-
- NOVEL, HIGHLY ACTIVE PYRAZOLO-PIPERIDINE SUBSTITUTED INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
-
The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.
- -
-
Page/Page column 122
(2019/05/22)
-
- Purification method for DL-alpha-amino caprolactam
-
The invention belongs to the technical field of the organic matter purification technology, and particularly relates to a purification method for DL-alpha-amino caprolactam. The preparation method comprises the following steps: S1: dissolving alpha-halogenated caprolactam and benzylamine in an organic solvent, adding alkali, controlling reaction temperature, and reacting to generate N-benzyl-DL-alpha-amino caprolactam; S2: adding the N-benzyl-DL-alpha-amino caprolactam generated by reaction in S1 into a reflux solvent, then, adding a catalyst and a hydrogen supply reagent, and carrying out reflux reaction to prepare a DL-alpha-amino caprolactam coarse product; S3: heating and dissolving the prepared DL-alpha-amino caprolactam coarse product by a recrystallization solvent, removing impurities during hotness, cooling, filtering, and taking solid, i.e. purified DL-alpha-amino caprolactam, wherein the recrystallization solvent is a mixed solvent obtained by mixing ethyl acetate, tetrahydrofuran and cyclohexanone at the mass ratio of (15-20):(6-8):5.
- -
-
Paragraph 0019-0039
(2019/02/21)
-
- Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation
-
A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.
- Fuentes de Arriba, ángel L.,Lenci, Elena,Sonawane, Mahendra,Formery, Odilon,Dixon, Darren J.
-
supporting information
p. 3655 - 3659
(2017/03/21)
-
- Transition-Metal-Free Amine Oxidation: A Chemoselective Strategy for the Late-Stage Formation of Lactams
-
A metal-free strategy for the formation of lactams via selective oxidation of cyclic secondary and tertiary amines is described. Molecular iodine facilitates both chemoselective and regioselective oxidation of C-H bonds directly adjacent to a cyclic amine. The mild conditions, functional group tolerance, and substrate scope are demonstrated using a suite of diverse small molecule cyclic amines, including clinically approved drug scaffolds.
- Griffiths, Robert J.,Burley, Glenn A.,Talbot, Eric P. A.
-
p. 870 - 873
(2017/02/26)
-
- MONONUCLEAR IRON COMPLEX AND ORGANIC SYNTHESIS REACTION USING SAME
-
Provided is a mononuclear iron complex that comprises an iron-silicon bond that is represented by formula (1) and that exhibits excellent catalyst activity in each of a hydrosilylation reaction, a hydrogenation reaction, and reduction of a carbonyl compound. In formula (1), R1-R6 either independently represent an alkyl group, an aryl group, an aralkyl group or the like that may be substituted with a hydrogen atom or X, or represent a crosslinking substituent in which at least one pair comprising one of R1-R3 and one of R4-R6 is combined. X represents a halogen atom, an organoxy group, or the like. L represents a two-electron ligand other than CO. When a plurality of L are present, the plurality of L may be the same as or different from each other. When two L are present, the two L may be bonded to each other. n and m independently represent an integer of 1 to 3 with the stipulation that n+m equals 3 or 4.
- -
-
-
- MONONUCLEAR RUTHENIUM COMPLEX AND ORGANIC SYNTHESIS REACTION USING SAME
-
Provided is a mononuclear ruthenium complex that comprises a ruthenium-silicon bond that is represented by formula (1) and that exhibits excellent catalyst activity in each of a hydrosilylation reaction, a hydrogenation reaction, and reduction of a carbon
- -
-
-
- Copper-Catalyzed Ligand-Free Amidation of Benzylic Hydrocarbons and Inactive Aliphatic Alkanes
-
An efficient copper-catalyzed amidation of benzylic hydrocarbons and inactive aliphatic alkanes with simple amides was developed. The protocol proceeded smoothly without any ligand, and a wide range of N-alkylated aromatic and aliphatic amides, sulfonamides, and imides were synthesized in good yields.
- Zeng, Hui-Ting,Huang, Jing-Mei
-
supporting information
p. 4276 - 4279
(2015/09/15)
-
- AZEPANE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS
-
Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.
- -
-
Paragraph 0724; 0725; 0726
(2015/07/22)
-
- AZEPANE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS
-
Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.
- -
-
Paragraph 0720
(2015/09/22)
-
- Palladium(II)-Catalyzed Allylic C H Oxidation of Hindered Substrates Featuring Tunable Selectivity Over Extent of Oxidation
-
The use of Oxone and a palladium(II) catalyst enables the efficient allylic C H oxidation of sterically hindered α-quaternary lactams which are unreactive under known conditions for similar transformations. This simple, safe, and effective system for C H activation allows for unusual tunable selectivity between a two-electron oxidation to the allylic acetates and a four-electron oxidation to the corresponding enals, with the dominant product depending on the presence or absence of water. The versatile synthetic utility of both the allylic acetate and enal products accessible through this methodology is also demonstrated.
- Xing, Xiangyou,O'Connor, Nicholas R.,Stoltz, Brian M.
-
supporting information
p. 11186 - 11190
(2016/07/06)
-
- Synthesis, spectral, and anti-microbial studies of thioiminium iodides and amine hydrochlorides
-
To avoid the undesired deprotonation during the addition of organolithium and organomagnesium reagents to ketones, the thioiminium salts, easily prepared from lactams and amides are converted into 2,2-disubstituted and 2-monosubstituted amines by reaction with simple nucleophiles such as organocerium and organocopper reagents. The reaction of thioiminium iodides with organocerium reagents derived by transmetalation of corresponding lithium reagents with anhydrous cerium(III) chloride has been investigated. These thioiminium iodides act as good electrophiles and accept alkylceriums towards bisaddition. The newly synthesized amines have been characterized by 1H and 13C NMR, IR and mass spectra. The amines have been converted into their hydrochlorides and characterized by COSY. These hydrochlorides have been subjected to antimicrobial screening with clinically isolated microorganisms, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella typhi and Candida albicans. The hydrochlorides show quite good activity against these bacteria and fungus.
- Britto, Sebastian,Renaud, Philippe,Nallu, Maruthai
-
supporting information
p. 489 - 493
(2013/12/04)
-
- DISUBSTITUTED AZEPAN OREXIN RECEPTOR ANTAGONISTS
-
The present invention is directed to disubstituted azepan and oxazepan amide compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin re
- -
-
Page/Page column 37
(2010/05/13)
-
- Hydrosilane reduction of tertiary carboxamides by iron carbonyl catalysts
-
Fox in the carboxamide: Reduction of tertiary carboxamides to their corresponding amines is catalyzed by [Fe(CO)5] or [Fe 3(CO)12], using 1,1,3,3tetramethyldlsiloxane (TMDS) as the reducing agent. The reaction proceeds under either thermal or photochemical conditions. Unlike the hydrosilane reduction of amides using platinum or ruthenlum catalysts, TMDS preferentially reduces a nitro group, even in the presence of competing amides.
- Sunada, Yusuke,Kawakami, Hiroko,Imaoka, Tsuyoshi,Motoyama, Yukihiro,Nagashima, Hideo
-
supporting information; experimental part
p. 9511 - 9514
(2010/03/24)
-
- Practical access to amines by platinum-catalyzed reduction of carboxamides with hydrosilanes: Synergy of dual Si-H groups leads to high efficiency and selectivity
-
The synergetic effect of two Si-H groups leads to efficient reduction of carboxamides to amines by platinum catalysts under mild conditions. The rate of the reaction is dependent on the distance of two Si-H groups; 1,1,3,3-tetramethyldisiloxane (TMDS) and 1,2-bis(dimethylsilyl)benzene are found to be an effective reducing reagent. The reduction of amides having other reducible functional groups such as NO2, CO2R, CN, CdC, Cl, and Br moieties proceeds with these groups remaining intact, providing a reliable method for the access to functionalized amine derivatives. The platinum-catalyzed reduction of amides with polymethylhydrosiloxane (PMHS) also proceeds under mild conditions. The reaction is accompanied by automatic removal of both platinum and silicon wastes as insoluble silicone resin, and the product is obtained by simple extraction. A mechanism involving double oxidative addition of TMDS to a platinum center is discussed.
- Hanada, Shiori,Tsutsumi, Emi,Motoyama, Yukihiro,Nagashima, Hideo
-
supporting information; experimental part
p. 15032 - 15040
(2010/01/29)
-
- NOVEL CYCLIC AMINOBENZOIC ACID DERIVATIVE
-
The present invention relates to cyclic amino benzoic acid derivatives which are effective in therapy of lipid metabolism abnormality, diabetes and the like as a human peroxisome proliferators-activated receptor (PPAR) agonist, in particular, as an agonist against human PPARα isoform, and addition salts thereof, and pharmaceutical compositions containing these compounds. A cyclic amino benzoic acid derivative represented by the general formula (1) [wherein a ring Ar represents an aryl group which may have substituent, or the like; Y represents a C1-C4 alkylene, C2-C4 alkenylene, C2-C4 alkynylene, or the like; Z represents an oxygen atom, sulfur atom or - (CH2)n- (n represents 0,1 or 2) ; X represents a hydrogen atom, halogen atom, lower alkyl group which may be substituted with a halogen atom, or the like; R represents a hydrogen atom or lower alkyl group, and -COOR substitutes for an ortho position or metha position of binding position of ring W] or a pharmaceutically acceptable salt thereof.
- -
-
Page/Page column 48
(2010/11/27)
-
- Method of treating addiction or dependence using a ligand for a monoamine receptor or transporter
-
One aspect of the present invention relates to a method of treating of drug addiction or drug dependence in a mammal, comprising the step of administering to a mammal in need thereof a therapuetically effective amount of a heterocyclic compound, e.g., a 3-substituted piperidine. In a preferred embodiment, the method of the present invention treats cocaine addiction or methamphetamine addiction.
- -
-
-
- 2-AMINOPYRIDINES AS INHIBITORS OF CYCLOOXYGENASE-2
-
The invention encompasses the novel compound of Formula (I) as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula (I). The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula (I).
- -
-
Page/Page column 28
(2010/02/11)
-
- Vasoactive agents
-
A vasoactive drug is provided which comprises a compound having GPR14-antagonizing activity or salts thereof.
- -
-
-
- Heterocyclic analgesic compounds and methods of use thereof
-
One aspect of the present invention relates to novel heterocyclic compounds. A second aspect of the present invention relates to the use of the novel heterocyclic compounds as ligands for various cellular receptors, including opiate receptors, other G-protein-coupled receptors, and ion channels. An additional aspect of the present invention relates to the use of the novel heterocyclic compounds as analgesics.
- -
-
-
- Heterocyclic analgesic compounds and methods of use thereof
-
One aspect of the present invention relates to novel heterocyclic compounds. A second aspect of the present invention relates to the use of the novel heterocyclic compounds as ligands for various cellular receptors, including opiate receptors, other G-protein-coupled receptors, and ion channels. An additional aspect of the present invention relates to the use of the novel heterocyclic compounds as analgesics.
- -
-
-
- USE OF POLYPEPTIDE
-
The present invention provides uses of a polypeptide having a ligand activity to a sensory epithelium neuropeptide-like receptor (SENR) which is a G protein-coupled receptor protein, and a DNA encoding the same. More specifically, the present invention provides an anti-attention-deficit-disorder or anti-narcolepsy agent, which comprises a polypeptide having a ligand activity for SENR or a salt thereof, as well as a method for screening compounds having an anti-attention-deficit-disorder or anti-narcolepsy activity or compounds having an anti-anxiety, anti-depression, anti-insomnia, anti-schizophrenia or anti-fear activity or salts thereof, which comprises using the above polypeptide or a precursor protein of the polypeptide or a salt thereof.
- -
-
-
- Ligands for monoamine receptors and transporters, and methods of use thereof
-
One aspect of the present invention relates to heterocyclic compounds. A second aspect of the present invention relates to the use of the heterocyclic compounds as ligands for various mammalian cellular receptors, including dopamine, serotonin, or norepinephrine transporters. The compounds of the present invention will find use in the treatment of numerous ailments, conditions and diseases which afflict mammals, including but not limited to addiction, anxiety, depression, sexual dysfunction, hypertension, migraine, Alzheimer's disease, obesity, emesis, psychosis, schizophrenia, Parkinson's disease, inflammatory pain, neuropathic pain, Lesche-Nyhane disease, Wilson's disease, and Tourette's syndrome. An additional aspect of the present invention relates to the synthesis of combinatorial libraries of the heterocyclic compounds, and the screening of those libraries for biological activity, e.g., in assays based on dopamine transporters.
- -
-
-
- Heterocyclic analgesic compounds and methods of use thereof
-
One aspect of the present invention relates to novel heterocyclic compounds. A second aspect of the present invention relates to the use of the novel heterocyclic compounds as ligands for various cellular receptors, including opiate receptors, other G-protein-coupled receptors, and ion channels. An additional aspect of the present invention relates to the use of the novel heterocyclic compounds as analgesics.
- -
-
-
- Reactions of alkyl azides and ketones as mediated by Lewis acids: Schmidt and Mannich reactions using azide precursors
-
The Lewis acid-promoted reactions of alkyl azides with ketones can afford several products. Chief among these result from a Schmidt-like insertion of the azide into the carbon - carbon bond adjacent to the carbonyl group. Alternatively, an acid-promoted r
- Desai, Pankaj,Schildknegt, Klaas,Agrios, Konstantinos A.,Mossman, Craig,Milligan, Gregory L.,Aube, Jeffrey
-
p. 7226 - 7232
(2007/10/03)
-
- 2-aminopyridines as inhibitors of cyclooxygenase-2
-
The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. STR1 The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
- -
-
-
- Total synthesis of (-)· and (+)-balanol
-
Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-∈-caprolactam.
- Lampe, John W.,Hughes, Philip F.,Biggers, Christopher K.,Smith, Shelley H.,Hu, Hong
-
p. 4572 - 4581
(2007/10/03)
-
- Two efficient syntheses of (±)-anti-N-benzyl-3-amino-4-hydroxyhexahydroazepine
-
Functionalization of ε-caprolactam or Beckmann rearrangement of the syn-oxime derivative of 3-ethoxy-2-cyclohexen-1-one provided efficient and high-yielding syntheses of (±)-anti-N-benzyl-3-amino-4-hydroxyhexahydroazepine, a key intermediate for the synth
- Hu, Hong,Jagdmann Jr., G. Erik,Hughes, Philip F.,Nichols, Jeffrey B.
-
p. 3659 - 3662
(2007/10/02)
-
- Preparation and epoxidation of conjugated lactams: Influence of ring size on epoxidation
-
α,β-Epoxy-lactams can be prepared from conjugated lactams by treatment with m-chloroperoxybenzoic acid. Good yields are obtained, however, only with 2-pyrrolidinone derivatives. The yield of epoxy-lactam diminishes dramatically as the size of the lactam ring increases.
- Li,Smith
-
p. 1265 - 1275
(2007/10/02)
-
- Syntheses of nitrogen heterocycles by means of amine-directed carbonylation and hydrocarbonylation
-
Amine-directed carbonylation of 2-allylpiperidine (5) gives 8-methyl-1-azabicyclononan-9-one (7) with extremely high regio- and stereoselectivity, which is promoted by a stoichiometric amount of 2 in the presence of hydrogen chloride.A c
- Zhang, Zhaoda,Ojima, Iwao
-
p. 281 - 289
(2007/10/02)
-
- TiCl4-Mediated Reactions of Alkyl Azides with Cyclic Ketones
-
The reaction of cyclic ketones with alkyl azides to afford N-alkyl lactams can be effected by TiCl4.
- Aube, Jeffrey,Milligan, Gregory L.,Mossman, Craig J.
-
p. 1635 - 1637
(2007/10/02)
-
- An Efficient Synthesis of Acetylated Bicyclic Hydroxypyrroles from Cyclic Lactams via Flash-Vacuum Pyrolysis of Meldrum's Acid Derivatives
-
The title compounds 9 were synthesized in three steps from cyclic lactams 2.After treatment of 2a-h with phosgene followed by the addition of Meldrum's acid to the chloroiminium chloride intermediates 3a-h, derivatives 4a-h were isolated in good yields.Compounds 4a-g were quantitatively converted to bicyclic enaminones 7a-g by flash-vacuum pyrolysis in the temperature range 480-600 deg C.In contrast, 4h provided 8h, the hydroxyprrole tautomer of 7h.The reaction takes place through the initial formation of (aminomethylene)ketenes 5a-h followed by a 1,4-hydrogen migration from the carbon adjacent to the nitrogen atom to the central carbon of the cumulenone.The lower temperature (480 deg C) needed for benzyl and N-carboalkoxy derivatives 4e-h in comparison with N-alkyl derivatives 4a-d (600 deg C) is correlated with gas-phase acidity of the migrating hydrogen atom.The hydroxypyrroles 8a-g, tautomers of 7a-g (78), were trapped with acetic anhydride, affording O-acetylated bicyclic hydroxypyrroles 9a-g.
- Pommelet, Jean-Claude,Dhimane, Hamid,Chuche, Josselin,Celerier, Jean-Pierre,Haddad, Mansour,Lhommet, Gerard
-
p. 5680 - 5685
(2007/10/02)
-
- OXIDATION OF ORGANIC NITROGEN COMPOUNDS BY MEANS OF RUTHENIUM TETROXIDE: SELECTIVE PREPARATION OF N-SUBSTITUTED LACTAMS
-
1-Formyl-, 1-acetyl-, and 1-benzoyl-perhydro-azepines and -azocines are oxidized by RuO4 to the corresponding N-acyllactams; the 1-benzyl analogues also undergo major endocyclic oxidation to 1-benzyllactams.
- Tangari, Nicola,Giovine, Maria,Morlacchi, Flaviano,Vetuschi, Claudio
-
p. 325 - 328
(2007/10/02)
-
- THE =C=S -> =C=O TRANSFORMATION USING THE SOFT NO(+)-SPECIES
-
The reaction of NaNO2 in acidic solution with thiocarbonyl compounds has been studied.Secondary- and tertiary thioamides, 1-benzyl-hexahydro-2H-azepine-2-thione, 5-ethyl-5-phenyl thiobarbituric acid, certain thiourea derivatives, 2H-1-benzopyran-2-thione, O,O-diphenyl-thiocarbonic ester, O,S-diphenyl-dithiocarbonic ester, N,N-dimethyl-S-phenyl-dithiocarbamatic ester, N-ethyl-N-phenyl-O-ethyl-thiocarbamatic ester are all converted into the corresponding carbonyl-analogues. 4,4'-Bis(dimethylamino)-thiobenzophenone (Michler's thioketone) gives 3-nitro-4,4'-bis(dimethylamino)-benzophenone at room temperature.At (-10 deg C)-(-5 deg C) the expected oxo compound is obtained as the main product together with 4-(N-nitroso-methylamino)-4'-(dimethylamino)-benzophenone.
- Joergensen, K. A.,Ghattas, A.-B.A.G.,Lawesson, S.-O.
-
p. 1163 - 1168
(2007/10/02)
-
- N-ALKYLATION OF AMIDES AND N-HETEROCYCLES WITH POTASSIUM FLUORIDE ON ALUMINA
-
Alumina coated with potassium fluoride promotes smooth N-alkylation of carboxamides, lactams, and other N-heterocycles with alkyl halides or dialkyl sulfate under mild conditions.
- Yamawaki, Junko,Ando, Takashi,Hanafusa, Terukiyo
-
p. 1143 - 1146
(2007/10/02)
-
- Hydroformylation of Bisolefinic Amine Derivatives Catalyzed by Cobalt and Rhodium
-
Three bisolefinic carbamates and five N,N-diallyl N-substituted amines have been subjected to hydroformylation conditions under catalysis by HCo(CO)4, Co(CO)8 and (Ph3P)3Rh(H)CO in an attempt to prepare heterocyclic ketones.The products differ with amines and carbamates and with catalyst.Carbamate 3 and HCo(CO)4 gave 3-pyrrolidinone (4) in 45percent yield.The cobalt-catalyzed reaction of 8 and rhodium-catalyzed reaction of 3 and of 8 afforded products arising from hydroformylation at the terminal olefinic carbon.These mixtures usually included 2-pyrrolidinone; cobalt-catalyzed hydroformylation of chlorinated allylamines 10-12 provided N-benzyl-2-pyrrolidinone (14) and N,N-dibutylbenzylamine (16).Direct synthesis of potential intermediates including 18 has permitted the delineation of mechanistic rationale.
- Garst, Michael E.,Lukton, David
-
p. 4433 - 4438
(2007/10/02)
-