Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-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 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.
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Materialwissenschaftliches Zentrum MZE, Building 30.48, Straße am Forum 7, 76131 Karlsruhe, Germany.
Andreas C
AC
Boukis
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Materialwissenschaftliches Zentrum MZE, Building 30.48, Straße am Forum 7, 76131 Karlsruhe, Germany.
Baptiste
B
Monney
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Materialwissenschaftliches Zentrum MZE, Building 30.48, Straße am Forum 7, 76131 Karlsruhe, Germany.
Michael A R
MA
Meier
Biginelli reaction; Passerini reaction; molecular diversity; multicomponent reactions; tandem reactions