39887-35-9Relevant articles and documents
Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis
Wang, Ming-Ming,Waser, Jér?me
, p. 16420 - 16424 (2020)
We report an oxidative ring-opening strategy to transform cyclopropylamides and cyclobutylamides into fluorinated imines. The imines can be isolated in their more stable hemiaminal form, with the fluorine atom installed selectively at the γ or δ position. Both inexpensive benzophenone with UVA light or organic and inorganic dyes with blue light could be used as photoredox catalysts to promote this process. Various fluorinated amines were then obtained by nucleophilic attack on the hemiaminals in one pot, giving access to a broad range of useful building blocks for medicinal chemistry.
A CO2-Catalyzed Transamidation Reaction
Yang, Yang,Liu, Jian,Kamounah, Fadhil S.,Ciancaleoni, Gianluca,Lee, Ji-Woong
, p. 16867 - 16881 (2021/11/18)
Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular,N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO2-catalyzed transamidation versus a N2atmosphere. Comparative Hammett studies and kinetic analysis were conducted to elucidate the catalytic activation mechanism of molecular CO2, which was supported by DFT calculations. We attributed the positive effect of CO2in the transamidation reaction to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO2
POTENTIAL CENTRAL NERVOUS SYSTEM ACTIVE AGENTS. 3. SYNTHESIS OF SOME SUBSTITUTED BENZAMIDES AND PHENYLACETAMIDES.
Agwada
, p. 231 - 235 (2007/10/02)
The preparation and special properties (IR, **1H NMR) are given for 45 benzamides and 10 phenylacetamides substituted on nitrogen with allyl, benzhydryl, benzyl, or cyclopropyl groups, and variously substituted on the acyl part with halo, methoxyl, methyl, or nitro groups. The benzamide derivatives were synthesized by the Schotten-Baumann method, and the phenylacetamide derivatives were prepared by heating the appropriate N-benzhydrylammonium salt in o-xylene. Thirty-one of the compounds are new.
