Synthesis of N-alkyl(acyl)-1,2,3,4-tetrahydro-4-methylspiro [quinoline-2-cyclohexanes] and their conversions

The alkylation and acylation of 1,2,3,4-tetrahydro-4-methylspiro[quinoline-2-cyclohexane] and its bromo (methyl) derivatives substituted in the benzene ring, as well as 1,2,3,4-tetrahydro-4-methylspiro[benzo(h)quinoline-2-cyclohexane], were studied. It was established that the N-allyl derivatives ofspiro[tetrahydroquinolinecyclohexanes] are converted to their 8-allyl-substituted analogs by the action of sulfuric acid, boron trifluoride etherate, and aluminum chloride. It was shown that the N-acyl-substituted spiro[tetrahydroquinolinecyclohexanes] are recyclized to spiro[indan-1-cyclohexanes] in phosphoric acid. © 1994 Plenum Publishing Corporation.