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

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 ob...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2017-01, Vol.13 (1), p.54-62
Main Authors: Boukis, Andreas C, Monney, Baptiste, Meier, Michael A R
Format: Article
Language:English
Subjects:
Biginelli reaction
Chemistry
Dichloromethane
Dimethyl sulfoxide
Energy consumption
Full Research Paper
molecular diversity
multicomponent reactions
Passerini reaction
Solvents
tandem reactions
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Summary: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(1 )-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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.13.7