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Issue 34, 2014
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N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives

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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

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Publication details

The article was received on 02 Jun 2014, accepted on 02 Jul 2014 and first published on 03 Jul 2014


Article type: Paper
DOI: 10.1039/C4OB01126K
Citation: Org. Biomol. Chem., 2014,12, 6653-6660
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    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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