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

Nehaal Ahmed,Vijay Chudasama,André Shamsabadi

doi:10.1021/acsomega.9b03417

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.

Highlights

2-Aminobenzophenones are a very important class of compounds in medicinal and organic chemistry
There has been a substantial number of recent reports for the synthesis of acyl hydrazides and their conversion into a variety of useful chemical functionalities.[33]
Facilely accessed acyl hydrazides have been reported as shelf-stable intermediates for the creation of esters, thioesters, amides,[34] ketones,[35] N-acyl carbamates,36 1H- and 2H-indazoles,[37] and 1,3,4-oxadiazoles,[38] as well as being employed as precursors for the formation of bioactive molecules such as hydroxamic acids[39] and macrocyclic enamides.[40]

Summary

Introduction

2-Aminobenzophenones are a very important class of compounds in medicinal and organic chemistry. We postulated that our methodology could be applied for the synthesis of medicinally relevant benzodiazepines

Methods

Results

Conclusion