Tetrahedron letters

New synthetic “tricks”. From aliphatic amines and amides to azides and/or how to convert RNHCOR′ into RNHCOR ″avoiding drastic hydrolyses

J Garcia, J Vilarrasa

Index: Garcia, Jordi; Vilarrasa, Jaume Tetrahedron Letters, 1987 , vol. 28, # 3 p. 341 - 342

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Citation Number: 7

Abstract

Abstract Controlled reduction of N-alkyl-N-nitrosoamides to hydrazides followed by nitrosation and fragmentation affords azides in 80% overall yields, under mild conditions. This simple idea is the basis of methods for the conversion of alkylamines and N- alkylamides to alkyl azides, of RNHCOR′ into RNHCOR ″or RN (COR‴) 2, and of lactames into ω-azido esters or ω-azido acids.