Triflic‐Acid‐Catalyzed Tandem Epoxide Rearrangement and Annulation with Alkynes: An Efficient Approach for Regioselective Synthesis of Naphthalenes

Abstract

A facile triflic acid catalyzed method to synthesize 1-arylnaphthalenes from one-pot annulation reaction of arylepoxides and arylalkynes has been reported. The annulation reaction involves a successive epoxide to carbonyl rearrangement, electrophilic attack of carbonyl on arylalkyne followed by cyclization catalyzed by triflic acid. The present catalyst effects this transformation at room temperature itself.

A Direct Method for Synthesis of Quinoxalines and Quinazolinones Using Epoxides as Alkyl Precursor

“…In 2021, Feng [37] reported the first catalytic asymmetric multi-insertion olefin addition reaction triggered by an epoxy-vinyl Meinwald rearrangement using a chiral N,Ndioxide/Sc III complex catalyst. Encouraged by these discoveries and to further explore the applications of epoxides [38][39][40][41][42], herein, we developed a method for synthesizing pyrrolo [1,2-a]quinoxalines and quinazolin-4-ones via a tandem Meinwald rearrangement and cyclization in one pot.…”