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Synthesis 2006(24): 4205-4211  
DOI: 10.1055/s-2006-950352
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Synthesis of 3-Methylene-4-aryl-1,3,4,5-tetrahydrobenzo[b][1,4]di­azepin-2-ones and 3-Arylmethylene-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-ylamines [1]

R. Pathak, S. Nag, S. Batra*
Medicinal Chemistry Division, Central Drug Research Institute, PO Box 173, Lucknow 226 001, India
Fax: +91(522)2623405; Fax: +91(522)2623938; e-Mail: batra_san@yahoo.co.uk;
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Publication History

Received 28 July 2006
Publication Date:
02 November 2006 (online)

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Abstract

A simple and convenient synthesis of 3-methylene-4-aryl-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-ones was accomplished by the SN2 nucleophilic substitution of the acetates of Baylis­-Hillman adducts of acrylate with 1,2-phenylenediamines, followed by base-mediated intramolecular cyclization. Similar substrates derived from the Baylis-Hillman adducts of acrylonitrile via Pinner’s reaction led to 3-arylmethylene-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-ylamines in good yields.

Key words

Baylis-Hillman - 1,2-phenylenediamine - diazipine - diazepin-2-ones - diazepin-2-ylamines

1

CDRI Communication No. 7050.

1

CDRI Communication No. 7050.