One-pot synthesis of 2-aryloxymethyl-1-cyanomethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline via rearrangement of the N-oxide from 1-aryloxy-4-tetrahydro-1-quinolylbut-2-yne

Abstract

1-Aryloxy-4-tetrahydro-1 -quinoylbut-2-yne (1), on treatment with m-chloroperbenzoic acid in dichloromethane at room temperature for 12 h, rearranged to give the bispyrroloquinoline derivative (3) in 30–45% yield. Addition of aqueous potassium cyanide to the intermediate (not isolated) gave the title compound (5) in 55–75% yield.