BARC/PUB/2016/0255

 
 

A Serendipitous Synthesis of 11a-Hydroxy-11,11a-dihydrobenzo[e]indeno[2,1-b][1,4]diazepine-10,12-dione Derivatives by Condensation of 2-Aminobenzamides with Ninhydrin in Water

 
     
 
Author(s)

Devi, R. V.; Garande, A. M.; Maity, D. K.; Bhate, P. M.
(HRDD)

Source

Journal of Organic Chemistry, 2016. Vol. 81 (4): pp. 1689-1695

ABSTRACT

Ninhydrin undergoes an unprecedented condensation reaction with various 2-aminobenzamide derivatives in boiling water to afford 11a-hydroxy-11,11a-dihydrobenzo-[e]indeno[2,1-b][1,4]diazepine-10,12-dione derivatives. These hitherto unreported products are easily isolated in high yield by a simple filtration step. An interesting “ortho effect” was observed in the condensation reaction of ninhydrin with 2-amino-N-phenylbenzamide derivatives having an orthosubstituent in the N-phenyl moiety wherein the corresponding expected 3′-phenyl-1′H-spiro[indene-2,2′-quinazoline]-1,3,4′(3′H)-triones were obtained.

 
 
SIRD Digital E-Sangrahay