A Novel Route for the Diastereoselective Synthesis of Dispiro [tetrahydroquinoline-bis(2,2-dimethyl[1,3]dioxane-4,6-dione)] Derivatives via a One-Pot Domino Multicomponent Reaction of Arylamines, Aromatic Aldehydes, and Meldrum's Acid

摘要

A protocol has been developed for the diastereoselective synthesis of dispiro[tetrahydroquinoline-bis(2,2-dimethyl[1,3] dioxane-4,6-dione)] derivatives via a one-pot domino multicomponent reaction of arylamines, aromatic aldehydes, and Meldrum's acid for the first time. The products, with remarkable diastereoselectivity, were successfully synthesized in acetic acid media in ambient temperature along with the suggested mechanism through combination of domino Knoevenagel, Michael, and Diels-Alder reactions. The products have been characterized by IR, mass, H-1 NMR, C-13 NMR spectroscopy, and elemental analyses. The stereoselectivity of compounds was established with crystallography and NMR spectroscopy.