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Synthesis 2016; 48(10): 1550-1560
DOI: 10.1055/s-0035-1561405
DOI: 10.1055/s-0035-1561405
paper
Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide
Further Information
Publication History
Received: 25 December 2015
Accepted after revision: 09 February 2016
Publication Date:
11 March 2016 (online)
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561405.
- Supporting Information
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