N-Substituted Ureas and Thioureas in Biginelli Reaction Promoted by Chlorotrimethylsilane: Convenient Synthesis of N1-Alkyl-, N1-Aryl-, and N1,N3-Dialkyl-3,4-Dihydropyrimidin-2(1H)-(thi)ones

Sergey V. Ryabukhin; Andrey S. Plaskon; Eugeniy N. Ostapchuk; Dmitriy M. Volochnyuk; Andrey A. Tolmachev

doi:10.1055/s-2007-965881

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Synthesis 2007(3): 417-427
DOI: 10.1055/s-2007-965881

PAPER

N-Substituted Ureas and Thioureas in Biginelli Reaction Promoted by Chlorotrimethylsilane: Convenient Synthesis of N1-Alkyl-, N1-Aryl-, and N1,N3-Dialkyl-3,4-Dihydropyrimidin-2(1H)-(thi)ones

Sergey V. Ryabukhin^a,b, Andrey S. Plaskon^a,b, Eugeniy N. Ostapchuk^a, Dmitriy M. Volochnyuk*^a,c, Andrey A. Tolmachev^b
^a Enamine Ltd, 23 A. Matrosova St, Kyiv, 01103, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
^b National Taras Shevchenko University, 62 Volodymyrska St, Kyiv-33, 01033, Ukraine
^c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02094, Ukraine

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Publication History

Received 10 October 2006
Publication Date:
12 January 2007 (online)

Abstract
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Abstract

The classical Biginelli reaction has been extended by the use of N-substituted ureas and thioureas. A set of N1-alkyl-, N1-aryl-, and N1,N3-dialkyl-3,4-dihydropyrimidin-2(1H)-(thi)ones was readily prepared in excellent yield when chlorotrimethylsilane in N,N-dimethylformamide was used as promoter and water scavenger.

Key words

Biginelli reaction - heterocycles - Lewis acid - multicomponent reaction - parallel synthesis

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