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Article info. : 2005; 2(4) (pp 244~337)


Novel One-Pot Synthesis of New Derivatives of Dihydropyrimidinones, Unusual Multisubstituted Imidazoline-2-ones: X-ray Crystallography Structure

S. Balalaiea,٭, M. Soleiman-Beigia and F. Romingerb

aDepartment of Chemistry, K.N.Toosi University of Technology, P.O.Box 15875-4416 Tehran -Iran, Fax +98-21- 2285 3650
bOrganisch-Chemisches Institut der Universitšt Heidelberg, Im Neuenheimer Feld 270, D-69120, Heidelberg, Germany

(Received 14 September2005, Accepted 2 November2005)

Three-component condensation of phenylglyoxal, alkyl acetoacetates or acetylacetone and urea proceeds smoothly, catalyzed by ZnCl2, to afford the corresponding new 3,4- dihydropyrimidinones. This reaction is also catalyzed by AlCl3:ZnCl2 (3:1) under microwave irradiation in solvent-free conditions. One-pot three-component condensation of dimethyl urea, acetylacetone or alkyl acetoacetate and phenylglyoxal catalyzed by ZnCl2 or AlCl3:ZnCl2 (3:1) yields new multisubstituted imidazoline-2-ones derivatives. Structures of products were studied by X-ray crystallographic data. The reaction of phenylglyoxal, urea and β-ketoesters in the presence of hydrochloric acid produces only 5-phenylhydantoins.

Keywords: Dihydropyrimidinones, ZnCl2, AlCl3:ZnCl2 (3:1), Imidazoline-2-one derivatives, X-Ray data, One-pot multicomponent reaction


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