Syngas as a synergistic reducing agent for selective reductive amination-a mild route to bioactive amines

Current approaches to the reductive amination are often nonselective, require complicated catalysts, or are not atom-economical. The application of syngas as a mild and selective reducing agent to aminate carbonyl compounds unstable under hygrogenation conditions with functional groups, which furnis...

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Bibliographic Details
Published in:New journal of chemistry 2023-06, Vol.47 (22), p.1514-1518
Main Authors: Podyacheva, Evgeniya, Balalaeva, Alexandra I, Afanasyev, Oleg I, Runikhina, Sofiya A, Chusova, Olga, Kozlov, Andrey S, Liao, Saihu, Chusov, Denis
Format: Article
Language:English
Subjects:
Amines
Amino acids
Carbonyl compounds
Carbonyls
Functional groups
Fungicides
Reducing agents
Substrates
Synthesis gas
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Summary:Current approaches to the reductive amination are often nonselective, require complicated catalysts, or are not atom-economical. The application of syngas as a mild and selective reducing agent to aminate carbonyl compounds unstable under hygrogenation conditions with functional groups, which furnished a broad substrate scope, is demonstrated herein. Amino acid precursor and furfurylamine derivative were prepared indicating the high selectivity of the protocol. Several products with antifungal activity higher than triadimefon were synthesized. Syngas (a mixture of H 2 and CO) is a synergistic reducing agent working much better than its components independently. In particular it allows to aminate carbonyl compounds with unstable functional groups furnishing the potential fungicides.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj01258a