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Synthesis 2004(16): 2659-2664  
DOI: 10.1055/s-2004-834860
PAPER
© Georg Thieme Verlag Stuttgart · New York

2-(3,4-Dihydro-4-oxo-2-quinazolinyl)acetonitriles in the Synthesis of New Condensed Pyrimidines

Yulian M. Volovenkoa, Evgeniy V. Blyumin*b, Tatiana A. Volovnenkoa, Tatiana V. Shokola, Oleg V. Shishkinc
a Kiev National Taras Schevchenko University, Chemical Department, Volodimirska str. 64, Kiev, 01033, Ukraine
b Darmstadt University of Technology, Institute of Organic Chemistry, Petersenstraße 22, 64287 Darmstadt, Germany
Fax: +49(6151)166016; e-Mail: evgeniy@oc.chemie.tu-darmstadt.de;
c Scientific Research Department of Alkali Halide Crystals, National Academy of Sciences of Ukraine, 60 Lenina ave., Khar’kov, 310001, Ukraine
Further Information

Publication History

Received 17 March 2004
Publication Date:
29 September 2004 (online)

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Abstract

The reaction of the title compounds with 5-chloro-2-(methylsulfonyl/methylthio)pyrimidine-4-carbonyl chlorides afforded a series of new nitriles (6, 7). In the reaction of 6 with aliphatic amines the replacement of the methylsulfonyl group took place to give products 8. Compounds 6 cyclized into 3-(methylsulfonyl)-5,12-dioxo-7,12-dihydro-5H-pyrimido[4′,5′:5,6]pyrido[2,1-b]quinazoline-6-carbonitriles in the presence of Et3N. An X-ray crystallographic study was carried out to confirm the structure of the new compounds unambiguously. The influence of basicity and steric factors on the course of this cyclization was discussed.

Key words

pyrimidines - cyclizations - nucleophilic aromatic substitutions - quinazolines - acylations

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Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].