Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions

Beilstein Journal of Organic Chemistry

Andreas C. Boukis¹  Baptiste Monney¹  Michael A. R. Meier¹ 

[1] Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Materialwissenschaftliches Zentrum MZE, Building 30.48, Straße am Forum 7, 76131 Karlsruhe, Germany;

关键词: Biginelli reaction;    molecular diversity;    multicomponent reactions;    Passerini reaction;    tandem reactions;   

DOI  :  10.3762/bjoc.13.7

来源: DOAJ

【 摘 要 】

The Biginelli reaction was combined with the Passerini reaction for the first time in a sequential multicomponent tandem reaction approach. After evaluation of all possible linker components and a suitable solvent system, highly functionalized dihydropyrimidone–α-acyloxycarboxamide compounds were obtained in good to excellent yields. In a first reaction step, different 3,4-dihydropyrimidin-2(1H)-one acids were synthesized, isolated and fully characterized. These products were subsequently used in a Passerini reaction utilizing a dichloromethane/dimethyl sulfoxide solvent mixture. By variation of the components in both multicomponent reactions, a large number of structurally diverse compounds could be synthesized. In addition, a one-pot Biginelli–Passerini tandem reaction was demonstrated. All products were carefully characterized via 1D and 2D NMR as well as IR and HRMS.

【 授权许可】

Unknown