A versatile and robust photocatalytic methodology to install the amide functional group into azomethine imine ions is described. This protocol is distinguished by its broad scope and mild reaction conditions, which are well suited for the preparation of structurally complex compounds in the form of amino acids, peptides, and small drug-like molecules. Moreover, the generated pyrazolidinone core could be easily converted into β-alanine analogues.
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Carbamoylation of Azomethine Imines via Visible-Light Photoredox Catalysis.
Org Lett
September 2021
Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, Washington Luís Highway, km 235, São Carlos, São Paulo 13565-905, Brazil.
A versatile and robust photocatalytic methodology to install the amide functional group into azomethine imine ions is described. This protocol is distinguished by its broad scope and mild reaction conditions, which are well suited for the preparation of structurally complex compounds in the form of amino acids, peptides, and small drug-like molecules. Moreover, the generated pyrazolidinone core could be easily converted into β-alanine analogues.
View Article and Find Full Text PDFMechanism of inhibition of the GluA1 AMPA receptor channel opening by the 2,3-benzodiazepine compound GYKI 52466 and a N-methyl-carbamoyl derivative.
Biochemistry
May 2014
Department of Chemistry, and Center for Neuroscience Research, University at Albany, SUNY , Albany, New York 12222, United States.
2,3-Benzodiazepine derivatives, also known as GYKI compounds, represent a group of the most promising synthetic inhibitors of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors. Here we investigate the mechanism of inhibition of the GluA1 channel opening and the site of inhibition by GYKI 52466 and its N-3 methyl-carbamoyl derivative, which we term as BDZ-f. GluA1 is a key AMPA receptor subunit involved in the brain function.
View Article and Find Full Text PDF(S,S)-(+)-pseudoephedrine alpha-iminoglyoxylamide as a chiral glycine cation equivalent: a modular and flexible approach to enantioenriched alpha-amino ketones.
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Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, Bilbao, Spain.
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View Article and Find Full Text PDFSynthetic enantiopure aziridinomitosenes: preparation, reactivity, and DNA alkylation studies.
J Am Chem Soc
December 2003
Departments of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
An enantiocontrolled route to aziridinomitosenes had been developed from l-serine methyl ester hydrochloride. The tetracyclic target ring system was assembled by an internal azomethine ylide cycloaddition reaction based on silver ion-assisted intramolecular oxazole alkylation and cyanide-induced ylide generation via a labile oxazoline intermediate (62 to 66). Other key steps include reductive detritylation of 26, methylation of the N-H aziridine 56, oxidation of the sensitive cyclohexenedione 68 to quinone 70, and carbamoylation using Fmoc-NCO.
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