Fast and Efficient One-Pot Three-Component Synthesis of Some 1,2,3,4-Tetrahydro-6-methyl-N-phenyl-5-pyrimidinecarboxamide Derivatives via Biginelli Condensation Reaction

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dc.authoridGulten, Sirin/0000-0003-1735-0501
dc.contributor.authorGulten, Sirin
dc.contributor.authorGezerl, Ufuk
dc.contributor.authorGundogan, Elmas Aksanli
dc.date.accessioned2025-01-27T20:39:28Z
dc.date.available2025-01-27T20:39:28Z
dc.date.issued2020
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractTetrahydropyrimidine (THPM) synthesis has an enormous importance in organic chemistry and especially in pharmaceutical applications. Pyrimidines are the most active class of N-containing heterocyclic compounds and have different biological properties. The heterocyclic ring system with a thio group occupy a unique position in medicinal chemistry. This type of compounds play an important role in synthetic drugs and in biological processes. Dihydropyrimidinethione derivatives occur widely in nature. Several modifications of TIIPM-5-carboxamides have attracted considerable interest of medicinal chemists due to their pharmacological and therapeutic properties. A series of 1,2,3,4-tetrahydro-2-pyrimidinone/thione derivatives bearing a phenylcarbamoyl group at C-5 position were synthesized by one-pot three-component Biginelli condensation reaction. The reaction of acetoacetanilide as the 1,3-dicarbonyl component with various aromatic aldehydes and urea/thiourea in the presence of a catalytic amount of p-toluenesulfonic acid monohydrate (PTSA.H2O) or concentrated HCl as an efficient catalyst leads to Biginelli compounds. We have prepared eight THPM 5-carboxamide derivatives, four of them are new compounds. Their structures were confirmed by spectroscopic techniques and elemental analysis. These compounds have potential applications in organic synthesis and medicinal chemistry. We have synthesized a series of THPM-5-carboxamides by simple and efficient three-component Biginelli condensation reaction. Significant benefits of the present procedure include: a) application of inexpensive, non-toxic, environmentally friendly and easily available catalysts, b) the reactions are easy to carry out without high temperature and the workup is very simple, c) the required reaction times are relatively short (30-80 min with HCl and 8-24 h with PTSA.H2O), d) compatibility with various functional groups, e) the products are isolated in good to excellent yields (50-95%).
dc.description.sponsorshipCanakkale Onsekiz Mart University [BAP 2008/28]
dc.description.sponsorshipThis work was supported in part by Canakkale Onsekiz Mart University (BAP 2008/28).
dc.identifier.doi10.2174/1570178616666190819142221
dc.identifier.endpage371
dc.identifier.issn1570-1786
dc.identifier.issn1875-6255
dc.identifier.issue5
dc.identifier.scopus2-s2.0-85083788942
dc.identifier.scopusqualityQ4
dc.identifier.startpage366
dc.identifier.urihttps://doi.org/10.2174/1570178616666190819142221
dc.identifier.urihttps://hdl.handle.net/20.500.12428/23954
dc.identifier.volume17
dc.identifier.wosWOS:000530097700006
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherBentham Science Publ Ltd
dc.relation.ispartofLetters in Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectAcetoacetanilide
dc.subjectBiginelli condensation
dc.subjectone-pot condensation
dc.subjecttetrahydropyrimidines
dc.subjectthiourea
dc.subjecturea
dc.titleFast and Efficient One-Pot Three-Component Synthesis of Some 1,2,3,4-Tetrahydro-6-methyl-N-phenyl-5-pyrimidinecarboxamide Derivatives via Biginelli Condensation Reaction
dc.typeArticle

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