What is it about?
Factorial design guided, energy-efficient, and versatile synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (DHPM) (Biginelli synthesis) was developed. The optimum levels of potential variables (benzyl-n-triethylammonium chloride (BTEAC) and glacial acetic acid) were determined through studies. The factorial design (32) analysis inferred the use of BTEAC (10.25 mol%) and glacial acetic acid (7.6 ml) as optimal for the 60 min condensation. Thirteen new 3,4- dihydropyrimidine-2-(1H)-one (DHPM) analogs were synthesized using optimized reaction conditions. The quaternary ammonium ion of BTEAC stabilizes the polarization of carbonyl group in aryl aldehydes and enolizable ketone (alkyl acetoacetate) to facilitate the cyclocondensation, in order to produce DHPMs through N-acyliminium ion and Michael adducts formation.
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Why is it important?
The biocompatible strategy, simple product isolation (non-chromatographic method), and good to excellent yields are attractive features of this new protocol. Hence, the newly developed methodology is superior to the literature methods.
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This page is a summary of: Application of Design of Experiments (DoE) Approach for the Optimiza-tion of Phase-transfer Catalyzed Biginelli Dihydropyrimidinone (DHPM) Synthesis, Letters in Organic Chemistry, August 2020, Bentham Science Publishers,
DOI: 10.2174/1570178617999200812133809.
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