☆ 4.5 Article

Syntheses of Tetrahydrobenzodiazepines via SN2-Type Ring-Opening of Activated Aziridines with 2-Bromobenzylamine Followed by Copper-Powder-Mediated C-N Bond Formation

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2015)

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY

Volume 4, Issue 10, Pages 1103-1111

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/ajoc.201500224

Keywords

2-bromobenzylamine; copper; cyclization; nitrogen heterocycles; tetrahydrobenzodiazepines

Categories

Chemistry, Organic

Funding

IIT-Kanpur
CSIR, India
UGC, India

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Abstract

A synthetic route to 2,3,4,5-tetrahydrobenzodiazepines has been devised through an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by an intramolecular cyclization through Cu-powder-mediated C-N bond formation. This operationally simple and extremely stereospecific ring-opening-cyclization approach is very efficient for the synthesis of a diverse array of the desired benzodiazepine derivatives in excellent yields of up to 94% and enantiomeric excess of up to >99%.

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