An efficient one-pot synthesis of phenol derivatives by ring opening and rearrangement of diels-alder cycloadducts of substituted furans using heterogeneous catalysis and microwave irradiation

Abstract

The use of silica-supported Lewis acids as catalysts ­under microwave irradiation promotes regiospecific opening of the 7-oxa bridge of Diels-Alder cycloadducts of furan derivatives and produces polysubstituted phenols in a single step. This rapid and ­efficient procedure permits the synthesis of tri-, tetra- and penta­substituted benzene derivatives by reaction of 2,5-dimethylfuran (1), 2-ethylfuran (2) and 2-methoxyfuran (3) with dienophiles such as dimethyl acetylenedicarboxylate and methyl propiolate.