Nafion-H catalyzed cyclocondensation reaction for the synthesis of octahydroquinazolinone derivatives

A facile and environmentally friendly Nafion-H catalyzed multicomponent reaction for synthesis of octahydroquinazolinone derivatives is described. In order to improve the yield and selectivity, the effects of the mole proportion of reactants (cyclic β-diketones, urea and aldehydes) and solvents were investigated. The ability to reuse the catalyst, high yields and easy purification are important features of this process. Interestingly, under similar conditions, the use of nicotinaldehyde and isonicotinaldehyde as the aldehyde component of the reaction gives unexpected products that are distinct from Biginelli products. All of the products were characterized by 1H NMR, 13C NMR, EI-MS and IR, and the structure of one Biglnelli product (4k) was determined by single-crystal X-ray diffraction.

Graphical abstractA facile and environmentally friendly Nafion-H catalyzed multicomponent reaction for synthesis of octahydroquinazolinone derivatives is described. The ability to reuse the catalyst, high yields and easy purification are important features of this process. All products are characterized by 1H NMR, 13C NMR, EI-MS and IR, and the structure of one Biglnelli product (4k) was determined by single-crystal X-ray diffraction.Figure optionsDownload full-size imageDownload as PowerPoint slide