NEW SYNTHETIC "TRICKS". FROM ALIPHATIC AMINES AND AMIDES TO AZIDES AND/OR HOW TO CONVERT RNHCOR' INTO RNHCOR" AVOIDING DRASTIC HYDROLYSES

Article abstract of DOI:10.1016/S0040-4039(00)95723-X

Controlled reduction of N-alkyl-N-nitrosoamides to hydrazides followed by nitrosation and fragmentation affords azides in 80percent 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.