Synlett 2018-03-23

Facile Access to 1,5-Benzodiazepines via Amine-Promoted (4+3) Annulations of δ-Acetoxy Allenoates with o-Diaminobenzenes under Mild Conditions

Wang, Yi-Fan, He, Cheng-Yu, Hou, Longlei, Tian, Ping, Lin, Guo-Qiang, Tong, Xiaofeng

Index: 10.1055/s-0037-1609347

Full Text: HTML

Abstract

An amine-promoted (4+3) annulation of δ-acetoxy allenoate with o-diaminobenzene is reported, providing a facile access to 1,5-benzodiazepine. This method features wide reaction scope, mild conditions, and readily available starting materials. The cascade reaction involves aza-Michael addition of o-diaminobenzene to allenoate, elimination of acetate group, and subsequent 1,6-aza-Michael addition.