Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides

Nehaal Ahmed; André Shamsabadi; Vijay Chudasama

doi:10.1021/acsomega.9b03417

Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides

ACS Omega. 2019 Dec 17;4(27):22601-22612. doi: 10.1021/acsomega.9b03417. eCollection 2019 Dec 31.

Authors

Nehaal Ahmed¹, André Shamsabadi¹, Vijay Chudasama¹

Affiliation

¹ Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, U.K.

Abstract

Herein, we report the transformation of readily accessed acyl hydrazides into protected 2-aminobenzophenones via a two-step process involving an aryne-based molecular rearrangement followed by a one-pot addition-elimination procedure. The assembly of the scaffold is tolerant of a wide variety of functional groups, and the carbamate group on the product can be facilely removed to afford highly valuable 2-aminobenzophenones. Application of the protocol was demonstrated in the synthesis of neurological medicine phenazepam.