Synthesis of heterocyclics via enamines. II. Reactions of Cyclohex-1-enyl -aniline, -morpholine and -piperidine with 1,1-Dimethyl-3-oxobutyl isothiocyanate

Abstract

The condensation of cyclohex-1-enylaniline (8) with 1,1-dimethyl-3- oxobutyl isothiocyanate (5) gave 1,4,5,6,7,8,9,10-octahydro-2,4,4- trimethyl-1-phenyl-1,5-benzodiazocine-6(1H)-thione (9) as the major product and 3-phenyl-4,6,6-trimethyl-1,2,3,6-tetrahydropyrimidine-2- thione (7; R = Ph) as the minor product. The similar condensations of (5) with cyclohex-1-enylmorpholine and cyclohex-1-enylpiperidine formed the 1-thiocarbamoyl derivatives through β-elimination of the intermediate (15).