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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

N-Bromoacetamide-mediated Domino Cyclization and Elimination of Homoallylic Trichloroacetimidates: A Novel Approach Toward the Synthesis of 1-bromo-2-amino-3-butene Derivatives

Rui Zhu, Kai Yu, Zhenhua Gu

Org Biomol Chem. 2014 Sep 14;12(34):6653-60.

PMID: 25029658

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP79152	N-Bromoacetamide		79-15-2	Price

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