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

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

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 simp...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 81; no. 4; pp. 1689 - 1695
Main Authors: Devi, Rajkumari Vijilata, Garande, Ashok M, Maity, Dilip K, Bhate, Prakash M
Format: Journal Article
Language:English
Published: United States American Chemical Society 19-02-2016
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Summary: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 ortho- substituent 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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02327