Streamlined Deamination of Diverse Primary Amines Enabled by Anomeric Amide
Ya Pan , Wentong Liu , Liliang Huang , Junhai Huang , Huangdi Feng
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (24) : 3597 -3602.
Given the ubiquity of amines in natural products, pharmaceuticals, and functional materials, the development of facile deamination methods offers a promising strategy to increase the diversity of chemicals in drug discovery. In this study, we design and synthesize a novel deamination reagent, N-(benzyloxy)-N-(isobutyryloxy)-4-nitrobenzamide, leveraging its unique properties to efficiently convert readily available primary amines into diverse aromatic and heteroaromatic compounds, aliphatic hydrocarbons, and alkyl esters. This method exhibits broad functional group tolerance, including carbonyl, alkynyl, and amino groups, and has been successfully applied to amino acids, peptides and marketed drugs. Furthermore, the scalability of the reaction, as well as its utility in the sequential functionalization/deamination modification and deutero-deamination of various primary amines, highlights the practical potential of this approach.
Deamination reagent / Primary amines / Benzothioamides / Functionalization / Deutero-deamination / Peptides / Amino acids / Synthetic methods
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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