Azidotrimethylsilane-mediated Schmidt rearrangement of 2-aryl-1,2,3,4-tetrahydro-1-methylsulfonyl-4-quinolones: non-regioselectivity of carbon migration

Abstract

Azidotrimethylsilane-mediated Schmidt rearrangement of 2-aryl-1-methylsulfonyl-1,2,3,4-tetrahydro-4-quinolones in trifluoroacetic acid was investigated. In contrast to the corresponding 2-aryl-1,2,3,4-tetrahydro-4-quinolone precursors, the N-methylsulfonyl derivatives displayed non-regioselectivity of carbon migration during nitrogen insertion affording the isomeric ring-expanded derivatives via alkyl and aryl migration.