Dimethylformamide-mediated synthesis and characterization of novel pyrazole- and pyrimidine-based 3,4- dihydropyrimidine-2(1H)-thione derivatives

Ajani, Olayinka O. and JOLAYEMI, Emmanuel G. and OWOLABI, Fisayo E. and Aderohunmu, D. V. and Akinsiku, A.A. and Owoeye, Taiwo Felicia (2019) Dimethylformamide-mediated synthesis and characterization of novel pyrazole- and pyrimidine-based 3,4- dihydropyrimidine-2(1H)-thione derivatives. In: 3rd International Conference on Science and Sustainable Development, 2019, Online.

PDF Download (1MB)

Abstract

Pyrimidine, an essential component of nucleic acid is currently reported for its potential application in Acquired Immune Deficiency Syndrome (AIDS) chemotherapy. Also, pyrazole nucleus, a versatile heterocyclic compound is gaining more attention in drug designs owing to its pharmacological therapeutic potentials. Hence, this present study deals with cost effective synthesis of 6-methyl-4-phenyl-5-(substituted-5-phenyl-4H-pyrazol-3-yl)-3,4- dihydropyrimidine-2(1H)-thione derivatives which are concisely known as pyrazole-based pyrimidine scaffolds. The multicomponent reaction of benzaldehyde, acetyl acetone and thiourea in the presence of catalytic amount of hydrochloric acid (HCl)ab initio produced 5- aceto-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine, 1. Later, room temperature Claisen- Schmidt condensation of precursor 1 with diverse aromatic aldehydes which were benzaldehyde derivatives led to the formation of α,β-unsaturated carbonyl side chain, 2a-h. Finally, the thermal annellation through synthetic cyclization furnished crude products which were purified by recrystallization to afford 6-methyl-4-phenyl-5-(substituted-5-phenyl-4Hpyrazol- 3-yl)-3,4-dihydropyrimidine-2(1H)-thione derivatives 3a-h in a cheap condition. The chemical structures were authenticated using IR, UV, 1H-NMR and 13C-NMR as well as analytical data. The final products 3a-h possessed good candidature for further investigation regarding their biological activities and pharmacological potential for new drug discovery.

Item Type:	Conference or Workshop Item (Paper)
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Engineering, Science and Mathematics > School of Chemistry
Depositing User:	nwokealisi
Date Deposited:	14 Mar 2023 10:54
Last Modified:	14 Mar 2023 10:54
URI:	http://eprints.covenantuniversity.edu.ng/id/eprint/16694

Actions (login required)

View Item