Ultrasound-Assisted Synthesis of Some New N-(Substituted Carboxylic Acid-2-yl)-6-Methyl-4-Substituted Phenyl-3, 4-Dihydropyrimidine-2(1H)-One Carboxamides

Authors: Karzan K. Hameed & Faiq H. S. Hussain

Abstract:  In this work, the starting material 6-methyl-4- substituted phenyl-3,4-dihydropyrimidine-2- (1H)-one-5-carboxylic acid ethyl ester (3a,b) have been prepared from the condensation of benzaldehyde (or anisaldehyde), urea and ethyl acetoacetate, in presence of an acid in ethanol under sonication, then hydrolysed to the corresponding acids (4a,b) which were chlorinated with SOCl2 to produce 6-methyl- 4-substituted phenyl-3, 4-dihydropyrimidine-2-(1H)-one-carbonyl chloride (5a,b). The compounds (5a,b) then subjected to react with different amino acids in the presence of LaCl3.7H2O as a catalyst using a green method (ultrasound assisted technique) to give a new series of N-(Substituted carboxylic acid-2- yl)-6-methyl-4-substituted phenyl-3,4- dihydropyrimidine-2-(1H)-one-5-carboxamide (6a-e and 7a-h). The structures of the synthesized compounds were characterized by using FT-IR, 1H-NMR, 13C-NMR and elemental analysis.

Keywords: Dihydropyrimidinone, Biginelli Reaction, Lacl3.7H2O, Amino Acids, Ultrasonic Technique, Green Chemistry
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doi: 10.23918/eajse.v4i2p61

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