SYNTHESIS OF CIS OR TRANS 4-HETEROAROMATIC SUBSTITUTED FURANO AND PYRANO[3,2-c]TETRAHYDROQUINOLINES BY ONE-POT IMINO DIELS-ALDER REACTIONS

摘要

-A mild and an efficient method for the synthesis of substituted furano and pyrano[3,2-c]tetrahydroquinoline derivatives was described, using the imino Diels-Alder reaction between 2-(4-aminophenyl)benzofuran, aromatic aldehyde, and cyclic enol ethers. Furthermore, 2-hydroxyalkyl-4-heteroaromatic substituted tetrahydrofurano[3,2-c]quinoline was synthesized with good yields through the same imino Diels-Alder reaction in the absence of aldehydes. The advantages of this procedure are mild reaction conditions, and good yields with high diastereoselectivity.