Diastereoselective synthesis of cis-fused pyrano and furanobenzopyrans catalyzed by indium trichloride or triphenyl phosphonium perchlorate

Indium trichloride (InCl3) and triphenyl phosphonium perchlorate (TPP) are found to be effective catalysts for the cyclization of o-hydroxyaldimines with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran at ambient temperature to afford novel pyrano and furanobenzopyran derivatives in excellent yields with high diastereoselectivity. One pot syntheses of pyrano and furanobenzopyrans from o-hydroxybenzaldehyde, aromatic amines and an enol ether under identical conditions is reported for the first time. Similarly, o-hydroxyaldimine reacted with ethyl vinyl ether to give 2-ethoxy-4-N-aryl aminobenzopyran in good yields.