Issue 34, 2014

N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives

Abstract

A practical synthesis of 1-bromo-2-amino-3-butene derivatives from homoallylic trichloroacetimidates was reported. Simply heating the mixture of substrates and N-bromoacetamide in DMF at 90 °C would give the desired products in moderate to excellent yields. The reaction may proceed through a domino bromo-cyclization and elimination pathway. The synthesis of 4,5-dihydrooxazoles from 1-bromo-2-amino-3-butene derivatives was also investigated.

Graphical abstract: N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives

Supplementary files

Article information

Article type
Paper
Submitted
02 Jun 2014
Accepted
02 Jul 2014
First published
03 Jul 2014

Org. Biomol. Chem., 2014,12, 6653-6660

N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives

R. Zhu, K. Yu and Z. Gu, Org. Biomol. Chem., 2014, 12, 6653 DOI: 10.1039/C4OB01126K

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