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