The Experts below are selected from a list of 171 Experts worldwide ranked by ideXlab platform
Stanislav Groysman - One of the best experts on this subject based on the ideXlab platform.
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ketenimine formation catalyzed by a high valent cobalt carbene in bulky alkoxide ligand environment
Organometallics, 2019Co-Authors: Amanda Grass, Nicholas S. Dewey, Richard L. Lord, Stanislav GroysmanAbstract:High-valent cobalt carbene Co(OR)2(═CPh2) (OR = OCtBu2Ph) undergoes reaction with various Isocyanides CNR′ (CNR′ = 2,6-dimethylphenyl Isocyanide, 4-methoxyphenyl Isocyanide, 2-chloro-6-methylphenyl Isocyanide, adamantyl Isocyanide) to yield the corresponding ketenimine. The reaction is accompanied by the formation of cobalt bis(alkoxide) bis(Isocyanide) complexes Co(OR)2(CNR)2, which were independently synthesized and characterized. DFT calculations suggest the mechanism proceeds through Isocyanide binding to Co, followed by intramolecular insertion into the Co–carbene bond to form the ketenimine. We have also conducted an investigation of the catalytic formation of ketenimines at room temperature using mixtures of diazoalkanes (diphenyldiazomethane, methyl diazo(phenyl)acetate, and ethyl diazoacetate) and Isocyanides (2,6-dimethylphenyl Isocyanide, 4-methoxyphenyl Isocyanide, adamantyl Isocyanide, Cyclohexyl Isocyanide, and benzyl Isocyanide). While no catalytic reactivity was observed for diphenyldiazom...
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Ketenimine Formation Catalyzed by a High-Valent Cobalt Carbene in Bulky Alkoxide Ligand Environment
2019Co-Authors: Amanda Grass, Nicholas S. Dewey, Richard L. Lord, Stanislav GroysmanAbstract:High-valent cobalt carbene Co(OR)2(CPh2) (OR = OCtBu2Ph) undergoes reaction with various Isocyanides CNR′ (CNR′ = 2,6-dimethylphenyl Isocyanide, 4-methoxyphenyl Isocyanide, 2-chloro-6-methylphenyl Isocyanide, adamantyl Isocyanide) to yield the corresponding ketenimine. The reaction is accompanied by the formation of cobalt bis(alkoxide) bis(Isocyanide) complexes Co(OR)2(CNR)2, which were independently synthesized and characterized. DFT calculations suggest the mechanism proceeds through Isocyanide binding to Co, followed by intramolecular insertion into the Co–carbene bond to form the ketenimine. We have also conducted an investigation of the catalytic formation of ketenimines at room temperature using mixtures of diazoalkanes (diphenyldiazomethane, methyl diazo(phenyl)acetate, and ethyl diazoacetate) and Isocyanides (2,6-dimethylphenyl Isocyanide, 4-methoxyphenyl Isocyanide, adamantyl Isocyanide, Cyclohexyl Isocyanide, and benzyl Isocyanide). While no catalytic reactivity was observed for diphenyldiazomethane, ester-substituted diazoalkanes (diazoesters) demonstrate catalytic turnover. Relatively high yields are observed for the reactions involving bulkier aliphatic substrates adamantyl and Cyclohexyl Isocyanides. Mechanistic studies suggest that the lack of catalytic reactivity involving diphenyldiazomethane results from the inability of Co(OR)2(CNR)2 to undergo carbene formation upon reaction with N2CPh2. In contrast, facile reaction is observed between Co(OR)2(CNR)2 and diazoesters, which enables the overall catalytic reactivity
Stefano Marcaccini - One of the best experts on this subject based on the ideXlab platform.
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synthesis of pseudopeptidic s 6 amino 5 oxo 1 4 diazepines and s 3 benzyl 2 oxo 1 4 benzodiazepines by an ugi 4cc staudinger aza wittig sequence
Tetrahedron, 2010Co-Authors: Paulina Lecinska, Nazaret Corres, Daniel Moreno, Maria Garciavalverde, Stefano Marcaccini, Tomas TorrobaAbstract:Sequential Ugi reaction between p-substituted arylglyoxals, alkylamines, Cyclohexyl Isocyanide and 3-azido-(S)-2-(tert-butoxycarbonylamino)propanoic acid, followed by a Staudinger/aza-Wittig cyclization in the presence of triphenylphosphine, gave rise to enantiomerically pure N-Cyclohexyl 4-alkyl-2-aryl-5-oxo-(S)-6-(tert-butoxycarbonylamino)-4,5,6,7-tetrahydro-1H-1,4-diazepine-3-carboxamides, that can be useful for new drug design. By the same sequence, p-substituted benzaldehydes, 2-aminobenzophenone, Cyclohexyl Isocyanide and (S)-3-phenyl-2-azidopropionic acid gave rise to N-Cyclohexyl 2-((S)-3-benzyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl)-(R/S)-2-arylacetamides.
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a one pot ugi four component synthesis of 2 3h oxazolone 4 carboxamides
Synlett, 2008Co-Authors: Maria Garciavalverde, Stefano Marcaccini, Sonia Macho, Teresa Rodriguez, Josefa Rojo, Tomas TorrobaAbstract:Ugi reaction between arylglyoxals, anilines, Cyclohexyl Isocyanide and trichloroacetic acid in dichloromethane, in the presence of molecular sieves, afforded 2(3 H)-oxazolone 4-carbox-amides in good yields by a one-pot process that involved an in situ spontaneous cyclization of the Ugi product through an intermediate ketone enolate and the chloroacetate carbonyl group. The synthesis is based on the ability of the trichloroacetyl group to function as a masked carbonic acid surrogate.
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studies on Isocyanides and related compounds synthesis of 1 4 benzodiazepine 2 5 diones via ugi four component condensation
Synthesis, 2002Co-Authors: Cristina Faggi, Stefano Marcaccini, R Pepino, Cruz M PozoAbstract:A convenient two-step synthesis of the title compounds based on the Isocyanide chemistry is reported. The Ugi four-component condensation between 4-chloro-2-nitrobenzoie acid (1). aldehydes 2, Cyclohexyl Isocyanide (3) and α-amino esters as the amino components afforded the expected nitro compounds 5 which were reductively cyclized to the desired 1,4-benzodiazepine-2,5-di-ones 7 via the intermediate amino derivatives 6.
Lindiwe A Nkabinde - One of the best experts on this subject based on the ideXlab platform.
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imidazo 1 2 a pyridin 3 amines as potential hiv 1 non nucleoside reverse transcriptase inhibitors
Bioorganic & Medicinal Chemistry, 2011Co-Authors: Moira L Bode, David Gravestock, Simon Sana Moleele, Christiaan W Van Der Westhuyzen, Stephen C Pelly, Paul A Steenkamp, Heinrich C Hoppe, Tasmiyah Khan, Lindiwe A NkabindeAbstract:Abstract During random screening of a small in-house library of compounds, certain substituted imidazo[1,2- a ]pyridines were found to be weak allosteric inhibitors of HIV-1 reverse transcriptase (RT). A library of these compounds was prepared using the Groebke reaction and a subset of compounds prepared from 2-chlorobenzaldehyde, Cyclohexyl Isocyanide and a 6-substituted 2-aminopyridine showed good inhibitory activity in enzymatic (RT) and HIV anti-infectivity MAGI whole cell assays. The compound showing the best anti-HIV-1 IIIB whole cell activity (MAGI IC 50 = 0.18 μM, IC 90 = 1.06 μM), along with a good selectivity index (>800), was 2-(2-chlorophenyl)-3-(Cyclohexylamino)imidazo[1,2- a ]pyridine-5-carbonitrile 38 .
Amanda Grass - One of the best experts on this subject based on the ideXlab platform.
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ketenimine formation catalyzed by a high valent cobalt carbene in bulky alkoxide ligand environment
Organometallics, 2019Co-Authors: Amanda Grass, Nicholas S. Dewey, Richard L. Lord, Stanislav GroysmanAbstract:High-valent cobalt carbene Co(OR)2(═CPh2) (OR = OCtBu2Ph) undergoes reaction with various Isocyanides CNR′ (CNR′ = 2,6-dimethylphenyl Isocyanide, 4-methoxyphenyl Isocyanide, 2-chloro-6-methylphenyl Isocyanide, adamantyl Isocyanide) to yield the corresponding ketenimine. The reaction is accompanied by the formation of cobalt bis(alkoxide) bis(Isocyanide) complexes Co(OR)2(CNR)2, which were independently synthesized and characterized. DFT calculations suggest the mechanism proceeds through Isocyanide binding to Co, followed by intramolecular insertion into the Co–carbene bond to form the ketenimine. We have also conducted an investigation of the catalytic formation of ketenimines at room temperature using mixtures of diazoalkanes (diphenyldiazomethane, methyl diazo(phenyl)acetate, and ethyl diazoacetate) and Isocyanides (2,6-dimethylphenyl Isocyanide, 4-methoxyphenyl Isocyanide, adamantyl Isocyanide, Cyclohexyl Isocyanide, and benzyl Isocyanide). While no catalytic reactivity was observed for diphenyldiazom...
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Ketenimine Formation Catalyzed by a High-Valent Cobalt Carbene in Bulky Alkoxide Ligand Environment
2019Co-Authors: Amanda Grass, Nicholas S. Dewey, Richard L. Lord, Stanislav GroysmanAbstract:High-valent cobalt carbene Co(OR)2(CPh2) (OR = OCtBu2Ph) undergoes reaction with various Isocyanides CNR′ (CNR′ = 2,6-dimethylphenyl Isocyanide, 4-methoxyphenyl Isocyanide, 2-chloro-6-methylphenyl Isocyanide, adamantyl Isocyanide) to yield the corresponding ketenimine. The reaction is accompanied by the formation of cobalt bis(alkoxide) bis(Isocyanide) complexes Co(OR)2(CNR)2, which were independently synthesized and characterized. DFT calculations suggest the mechanism proceeds through Isocyanide binding to Co, followed by intramolecular insertion into the Co–carbene bond to form the ketenimine. We have also conducted an investigation of the catalytic formation of ketenimines at room temperature using mixtures of diazoalkanes (diphenyldiazomethane, methyl diazo(phenyl)acetate, and ethyl diazoacetate) and Isocyanides (2,6-dimethylphenyl Isocyanide, 4-methoxyphenyl Isocyanide, adamantyl Isocyanide, Cyclohexyl Isocyanide, and benzyl Isocyanide). While no catalytic reactivity was observed for diphenyldiazomethane, ester-substituted diazoalkanes (diazoesters) demonstrate catalytic turnover. Relatively high yields are observed for the reactions involving bulkier aliphatic substrates adamantyl and Cyclohexyl Isocyanides. Mechanistic studies suggest that the lack of catalytic reactivity involving diphenyldiazomethane results from the inability of Co(OR)2(CNR)2 to undergo carbene formation upon reaction with N2CPh2. In contrast, facile reaction is observed between Co(OR)2(CNR)2 and diazoesters, which enables the overall catalytic reactivity
Cruz M Pozo - One of the best experts on this subject based on the ideXlab platform.
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studies on Isocyanides and related compounds synthesis of 1 4 benzodiazepine 2 5 diones via ugi four component condensation
Synthesis, 2002Co-Authors: Cristina Faggi, Stefano Marcaccini, R Pepino, Cruz M PozoAbstract:A convenient two-step synthesis of the title compounds based on the Isocyanide chemistry is reported. The Ugi four-component condensation between 4-chloro-2-nitrobenzoie acid (1). aldehydes 2, Cyclohexyl Isocyanide (3) and α-amino esters as the amino components afforded the expected nitro compounds 5 which were reductively cyclized to the desired 1,4-benzodiazepine-2,5-di-ones 7 via the intermediate amino derivatives 6.
