Table of Contents Author Guidelines Submit a Manuscript
Advances in Chemistry
Volume 2014, Article ID 628326, 6 pages
http://dx.doi.org/10.1155/2014/628326
Research Article

A Simple and Advantageous Synthesis of the Privileged 1,4-Benzodiazepine Nucleus

Department of Chemistry, Banasthali University, Banasthali, Rajasthan 304022, India

Received 30 April 2014; Revised 5 July 2014; Accepted 11 July 2014; Published 11 August 2014

Academic Editor: Hideto Miyabe

Copyright © 2014 Neetu Jain and Dharma Kishore. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A novel domino approach has been described for an easy access of the privileged nucleus of 5-carbomethoxy substituted 1,4-benzodiazepin-2-ones 4(ai) from an in situ methanolic hydrolysis of an incipient species formed from the interaction of 1-chloroacetylisatin 2(ai), hexamethyldisilazane, and n-butyl lithium. The reaction is believed to take place through a consecutive series of intramolecular reactions in a cascade to first generate a highly reactive carbene intermediate 3(ai) from 1-chloroacetylisatin and n-butyl lithium which is simultaneously trapped by hexamethyldisilazane before undergoing its in situ hydrolysis with methanol to initiate its concomitant cyclocondensation to produce 4(ai) in high yield and purity.