Reactions of dihydroquinolines and dihydroisoquinolines with arenesulphonyl azides

Abstract

Tosyl azide reacts with 1,4-dihydro-1-methylquinoline-4-carbonitrile in ethyl acetate solution to form 1,2,3,4-tetrahydro-1-methyl-2-p-tolylsulphonyliminoquinoline-4-carbonitrile; in methanol, 1,2-dihydro-1-methyl-2-p-tolylsulphonyliminoquinoline-4-carbonitrile is also formed. 1,2-Dihydro-2-methylisoquinoline-1-carbonitrile reacts with tosyl azide yielding a mixture of 2,3-dihydro-2-methyl-3-p-tolylsulphonyliminoisoquinoline and the corresponding 1-carbonitrile.