Chemoselective Sequential Reactions for the Synthesis of 12H-Benzo[a]xanthenes and Dihydro-1H-naphtho[1,2-e][1,3]oxazines

Abstract

Novel sequential Betti–Ullmann and Betti–C–H activation reactions for the synthesis of 12H-benzo[a]xanthenes and dihydro-1H-naphtho[1,2-e][1,3]oxazines have been developed. Depending on the used conditions selective Ullmann-type arylation or α-C-H aryloxylation of 2-bromophenyl alkylaminonaphthols occurred. A simple, fast, green, and high-yielding method for the synthesis of aminonaphthols catalyzed by bismuth(III) chloride under solvent-free conditions is reported.