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Synthesis 2012(5): 800-804  
DOI: 10.1055/s-0031-1289691
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Dibenzo[b,e][1,4]diazepin-1-ones

Monica Nardi*a, Annalisa Cozzaa, Antonio De Ninoa, Manuela Oliveriob, Antonio Procopiob
a Dipartimento di Chimica, Università della Calabria, ponte Bucci cubo 12/c, 87030 Arcavacata di Rende (Cs), Italy
Fax: +39(0984)493077; e-Mail: nardi@unical.it;
b Dipartimento di Scienze Farmacobiologico, Università Magna Græcia di Catanzaro, Complesso Ninì Barbieri, 88021 Roccelletta di Borgia (CZ), Italy
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Publication History

Received 9 November 2011
Publication Date:
03 February 2012 (online)

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Abstract

A simple and efficient method for the synthesis of wide range of 3,3-dimethyl-11-alkyl or aryl 2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepin-1-ones, recently reported as hepatitis C virus (HCV) NS5B polymerase inhibitors, is presented. The proposed method consists of one-pot condensation between 1,2-phenylenediamine and 5,5-dimethylcyclohexane-1,3-dione (dimedone) followed by cyclization with various alkyl and aryl acyl chlorides catalyzed by Er(III) triflate. With respect to methods previously reported, the proposed one-pot procedure furnishes appreciably higher yield of product in shorter reaction time.

Key words

amines - azo compounds - drugs - Lewis acids - lanthanides

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