Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide

Ivana I. Jevtić, Ljiljana Došen-Mićović, Evica R. Ivanović, Milovan D. Ivanović*

*Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia, Email: misaichem.bg.ac.rs

I. I. Jevtić, L. Došen-Mićović, E. R. Ivanović, M. D. Ivanović, Synthesis, 2016, 48, 1550-1560.

DOI: 10.1055/s-0035-1561405

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Abstract

An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides provides methyl and benzyl carbamates in high yields in the presence of N-bromoacetamide and lithium hydroxide or lithium methoxide. β-Phenylamino amides gave five-membered cyclic ureas stereospecifically.

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Key Words

Hofmann rearrangement, amides, carbamates, stereoselectivity, cyclization, heterocycles

ID: J66-Y2016