Synthesis of fused quinazolinones via visible light induced cyclization of 2-aminobenzaldehydes with tetrahydroisoquinolines

Abstract

This study reports a novel method for the synthesis of fused quinazolinones by visible-light-induced cyclization of 2-aminobenzaldehydes and tetrahydroisoquinolines. The reaction is easily carried out by irradiation with a blue LED in the presence of 9-fluorenone and air. A broad substrate scope with good tolerance of functionalities was observed under the optimized reaction conditions. Moreover, using 2-aminophenone as the substrate and under similar reaction conditions, the same product was obtained when a carbon was removed. The bio-active naturally occurring alkaloid rutaecarpine could be obtained by this strategy. The success of the reaction on the gram-scale and the further transformation of the substrate demonstrated the synthetic practicability of this reaction.