Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,- c]coumarins and Furo[3,2,- c]pyran-4-ones via Nonsymmetric Triarylmethanes

Org Lett. 2020 Mar 6;22(5):1801-1806. doi: 10.1021/acs.orglett.0c00123. Epub 2020 Feb 25.

Abstract

A one-pot synthesis of functionalized 2,3-disubstituted furo[3,2,-c]coumarins and furo[3,2,-c]pyran-4-ones under hydrated ferric sulfate catalysis was performed. It was revealed that the reaction proceeds with intramolecular cyclofunctionalization of nonsymmetric triarylmethanes via ring opening of 2-methylfuran followed by recyclization, resulting in the selective formation of desired products. The versatility of this method was demonstrated via the succinct synthesis of an anticoagulant agent analogue and 2,3-disubstituted benzofurans.

Publication types

  • Research Support, Non-U.S. Gov't