A tandem one-pot, microwave-assisted synthesis of regiochemically differentiated 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones

Ravindra A De Silva; Soumava Santra; Peter R Andreana

doi:10.1021/ol801841m

A tandem one-pot, microwave-assisted synthesis of regiochemically differentiated 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones

Org Lett. 2008 Oct 16;10(20):4541-4. doi: 10.1021/ol801841m. Epub 2008 Sep 24.

Authors

Ravindra A De Silva¹, Soumava Santra, Peter R Andreana

Affiliation

¹ Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.

PMID: 18811177
DOI: 10.1021/ol801841m

Abstract

A one-pot, two-step synthesis of the title compounds employs a multicomponent Ugi condensation reaction, microwave irradiation, and Fe(0) as a reductant. Two pathways are accessible; both routes utilize bifunctional, o-nitro-substituted arenes leading to either C2, N4, C5 substitution (A) or C2, N4 substitution (B).