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

Boukis, Andreas C; Monney, Baptiste; Meier, Michael A R

Abstract (englisch):
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.

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Verlagsausgabe §
DOI: 10.5445/IR/1000067020
Veröffentlicht am 01.02.2018
DOI: 10.3762/bjoc.13.7
Zitationen: 8
Web of Science
Zitationen: 7
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Jahr 2017
Sprache Englisch
Identifikator ISSN: 1860-5397
KITopen-ID: 1000067020
Erschienen in Beilstein journal of organic chemistry
Band 13
Seiten 54–62
Schlagworte Biginelli reaction, molecular diversity, multicomponent reactions, Passerini reaction, tandem reactions
Nachgewiesen in Scopus
Web of Science
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