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Synthesis 2006(18): 3067-3074  
DOI: 10.1055/s-2006-950182
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Cyclization of Carbon Nucleophiles with 2-Isothiocyanatobenzoni­trile (ITCB): Synthesis of 4-Alkylidene-3,4-dihydroquinazoline-2(1H)thiones

Uwe Albrechta, Helmut Reinkeb, Peter Langer*b,c
a Institut für Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany
b Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
c Leibniz-Institut für Katalyse e. V. , Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 13 March 2006
Publication Date:
15 August 2006 (online)

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Abstract

The one-pot cyclization of 2-isothiocyanatobenzonitrile (ITCB) with carbon nucleophiles afforded 4-alkylidene-3,4-dihy­droquinazoline-2(1H)thiones with very good E diastereoselectivity.

Key words

cyclizations - heterocycles - isothiocyanates - one-pot reactions

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15

Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-601337 (8), CCDC-601338 (9a), and CCDC-601339 (9c). Copies of this data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk) or via www.ccdc.cam.ac.uk/conts/retrieving.html.

21

Jiao, H.; Langer, P., unpublished results.