Studies in aza-Claisen rearrangement: synthesis of dimedone-annelated unusual heterocycles

A number of 3-N-(4′-aryloxybut-2′-ynyl)N-methyl amino-5,5-dimethyl cyclohex-2-enones are synthesized in 62–65% yield by refluxing 3-chloro-5,5-dimethyl cyclohex-2-enone with a number of 4-aryloxy-4-chlorobut-2-ynes in ethanol for 4 h. The amines are then heated in refluxing chlorobenzene to give 7,7-dimethyl-1,2,3,6,7,8-hexahydro-4-aryloxymethylene-1-methyl quinoline-5-one in 75–80% yields.