Efficient Ce(NO3)3·6H2O-Catalyzed Solvent-Free Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones.docVIP

Molecules 2006, 11, 649-654 molecules ISSN 1420-3049 Full Paper Efficient Ce(NO3)3·6H2O-Catalyzed Solvent-Free Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Mehdi Adib,* Khadijeh Ghanbary, Manizheh Mostofi and Mohammad Reza Ganjali School of Chemistry, University College of Science, University of Tehran, P. O. Box 14155-6455, Tehran, Iran * Author to whom correspondence should be addressed; Tel/fax: +98(21 E-mail: madib@khayam.ut.ac.ir Received: 27 October 2005; in revised form: 9 May 2006/ Accepted: 23 August 2006 / Published: 23 August 2006 Abstract: Cerium(III) nitrate hexahydrate efficiently catalyzes the three-component Biginelli reaction under solvent-free conditions of an aldehyde, a β-keto ester or β- diketone and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)- ones or –thiones in excellent yields. Keywords: Dihydropyrimidinones; cerium(III) nitrate; Biginelli reaction; solvent-free synthesis. Introduction 3,4-Dihydropyrimidin-2(1H)-ones (DHPM) and their sulfur analogs have been reported to possess remarkable pharmacological properties. Some of which have antiviral, antitumor, antibacterial, antiinflammatory, and antihypertensive activities [1-5], some are calcium channel modulators [6], and α1a adrenoceptor-selective antagonists [7]. The structurally rather simple DHPM monastrol (Figure 1) specifically inhibits the mitotic kinesin Eg5 motor protein and can be considered as a new lead for the development of anticancer drugs [8]. The batzelladine alkaloids A and B (Figure 1) inhibit the binding of HIV envelope protein gp-120 to human CD4 cells and, therefore, are potential new leads for AIDS therapy [9]. As a result new synthetic methods for the efficient preparation of these heterocyclic compounds are of great importance. Very recently, several modified and improved procedures for the  Molecules 2006, 11 650 one-pot synthesis of dihydropyrim