The regioselective one-pot four-component synthesis of novel functionalized 4H-pyrano[2, 3-b]quinoline derivatives using DABCO as a homogeneous organocatalyst.

Abstract

This study deals with the synthesis of the regioselective and facile domino one-pot four-component reaction of 2-chloroquinoline-3-carbaldehydes, 1, 3-cyclodione compounds (as cyclic active methylene), ethyl acetoacetate (as β-keto ester), and hydrazine hydrate in the presence of DABCO as a homogeneous organocatalyst yielding a novel series of 4H-pyrano[2, 3-b]quinolones. This multicomponent reaction has some advantages; the significant one is C-O bond formation under metal-free conditions. Other benefits include simple procedure, mild and green condition, high yield, easy purification, and excellent regioselectivity. All polycyclic products (7a-k, 11 new compounds) were characterized by IR, 1H NMR, 13C NMR, and mass spectra.