Synthesis of Diverse Indene Derivatives from 1‑Diazonaphthalen-2(1<i>H</i>)‑ones via Thermal Cascade Reactions

Abstract

A sequential Wolff rearrangement of 1-diazonaphthalen-2(1<i>H</i>)-ones followed by trapping of the ketene intermediate with primary and aromatic amines or alcohols and phenols in the presence of various aldehydes generates 1<i>H</i>-indene-3-carboxamides or 1<i>H</i>-indene-3-carboxylates. This constitutes an unprecedented three-component coupling reaction that allows for the synthesis of functionalized indene derivatives under catalyst-free thermal conditions