Convenient Synthesis of Benzofuro[3,2-b]quinolines from 1-Azadienes and Arynes

Abstract

An efficient method has been developed for the synthesis of benzofuro[3,2-b]quinolines through tandem [4+2] cycloaddition/ aromatization under transition-metal-free conditions. A range of aurone­-derived N-tosyl-1-azadienes smoothly reacted with arynes, generated­ in situ via fluoride ion-induced 1,2-elimination of 2-(trimethyl­silyl)aryl triflates, delivering structurally diverse benzofuro[3,2-b]quinolines in moderate to good yields.

Key words

1-azadienes - arynes - benzofuro[3,2-b]quinolines - aromatization - cycloaddition

Publication History

Received: 10 June 2021

Accepted after revision: 14 July 2021

Accepted Manuscript online:
14 July 2021

Article published online:
12 August 2021

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