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Synthesis 2009(15): 2579-2583  
DOI: 10.1055/s-0029-1216868
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Versatile, Unexpected, One-Pot Regioselective Synthesis of a New Class of 1,3-Diazepinoindolones by Reaction of Pyranoindolones with Monosubstituted Ureas

Despina Livadiotou, Constantinos A. Tsoleridis*, Julia Stephanidou-Stephanatou*
Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Macedonia, Greece
Fax: +30(2310)997679; e-Mail: tsolerid@chem.auth.gr; e-Mail: ioulia@chem.auth.gr;
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Publication History

Received 11 March 2009
Publication Date:
26 June 2009 (online)

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Abstract

The regioselective one-pot synthesis of a new class of 4,6-dihydro[1,3]diazepino[5,6-b]indol-3(2H)-ones, in very good yields, via reaction of pyranoindolones with monosubstituted ureas is described. Reaction of N,N′-disubstituted ureas with pyranoindol­ones, under similar conditions, gave the corresponding β-carbolin­ones. The reaction mechanisms leading to both types of product are discussed and the structures are confirmed by spectroscopic techniques.

Key words

bisnucleophiles - carbenes - diazepinoindolones - pyranoindolones - substituted ureas - one-pot reaction