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| PAPER | Synthesis 2007: 417-427
DOI: 10.1055/s-2007-965881 |
© Georg Thieme Verlag Stuttgart · New York
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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
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| Sergey V. Ryabukhina,b, Andrey S. Plaskona,b, Eugeniy N. Ostapchuka, Dmitriy M. Volochnyuk*a,c, Andrey A. Tolmachevb |
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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Received
10 October 2006 |
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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