Construction of the 1,5-Benzodiazepine Skeleton from o-Phenylendiamine and Propargylic Alcohols via a Domino Gold-Catalyzed Hydroamination/Cyclization Process

Sandro Cacchi; Giancarlo Fabrizi; Antonella Goggiamani; Antonia Iazzetti

doi:10.1021/acs.orglett.6b01720

Construction of the 1,5-Benzodiazepine Skeleton from o-Phenylendiamine and Propargylic Alcohols via a Domino Gold-Catalyzed Hydroamination/Cyclization Process

Org Lett. 2016 Aug 5;18(15):3511-3. doi: 10.1021/acs.orglett.6b01720. Epub 2016 Jul 28.

Authors

Sandro Cacchi¹, Giancarlo Fabrizi¹, Antonella Goggiamani¹, Antonia Iazzetti¹

Affiliation

¹ Dipartimento di Chimica e Tecnologie del Farmaco, La Sapienza, Università di Roma , P.le A. Moro 5, 00185 Rome, Italy.

PMID: 27467193
DOI: 10.1021/acs.orglett.6b01720

Abstract

The gold-catalyzed reaction of o-phenylendiamine with propargylic alcohols affords 1,5-benzodiazepines bearing different substituents on the 2 and 4 positions. The method allows even for the selective preparation of 4-substituted 1,5-benzodiazepine derivatives.

Publication types

Research Support, Non-U.S. Gov't