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 (free Supporting Information)
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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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Hofmann rearrangement, amides, carbamates, stereoselectivity, cyclization, heterocycles