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 discov...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.展开更多
基金the National Natural Science Foundation of China(Nos.22578264,22078192)Natural Science Foundation of Shanghai(25ZR1401147)National Key Research and Development Program of China(Nos.2023YFC2412400,2023YFC2412403)for financial support.
文摘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.
