Organocatalyzed Synthesis of Dihydropyrimidinone/Thiones via Biginelli Condensation Reaction
Publish place: 26th Iranian Seminar on Organic Chemistry
Publish Year: 1397
نوع سند: مقاله کنفرانسی
زبان: English
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شناسه ملی سند علمی:
ISOC26_133
تاریخ نمایه سازی: 2 شهریور 1398
Abstract:
Compounds containing 3,4-dihydropyrimidonone/thione frameworks are best known for theirbiological and pharmacological activities. Due to the therapeutic properties of some 3,4-dihydropyrimidonones (DHPMs) and their applications in the pharmaceutical industry, discoveryefficient and cost-effective methods for the synthesis of these compounds is a concernof many organic chemists. In general, the main method for the synthesis of DHPMs is a onepotmulticomponent reaction (MCR) of 1,3-dicarbonyl compounds, various aldehydes, andurea/thiourea derivatives called Biginelli reaction. Generally, this MCR has been catalyzedusing various reagents such as Lewis acids, organoacids, organic and inorganic bases, inorganicacids, nanomaterials, supported catalysts, and metal-organic frameworks [1-3]. In thepresent work, we have synthesized 2-benzyl-1-sulfopyridin-1-ium via sulfonation processandused it to the synthesis of DHPMs through a MCR technique. The three-component reactionof ethyl acetoacetate, various aromatic aldehydes, and urea/thiourea under solvent conditionin the presence of 2-benzyl-1-sulfopyridin-1-ium led to the formation of 3,4-dihydropyrimidonone/thione heterocycles in good to excellent yields (Fig. 1). This procedurehas notable features, including relatively shorter reaction times, simplicity, and environmentallyfriendliness.
Authors
Mohadeseh Goli
School of Chemistry, Damghan University, Damghan, Iran
Hamzeh Kiyani
School of Chemistry, Damghan University, Damghan, Iran