Hofmann Rearrangement of Carboxamides Mediated by N-Bromo­acetamide

Abstract

An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N-bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. β-Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.

Key words

Hofmann rearrangement - amides - stereoselectivity - cyclization - heterocycles

• References

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