Reaction of 1-methylthio-3,4-dihydroisoquinolines with amines

Article abstract of DOI:10.1007/BF01164868

A study was carried out on the reaction of 1-methylthio-3,4-dihydroisoquinolines with aromatic and aliphatic amines, thiourea, semicarbazide, and thiosemicarbazide. The reactions with anthranilic acid and 2-amino-3-carboethoxy-4,5-dimethylthiophene give 6,6-dimethyl-5,6-dihydro-8H-isoquino[1,2-b]quinazolin-8-one and6,6,9,10-tetramethyl-5,6-dihydro-8H-benzo[i]thieno[2,3-b]quinolizin-8-one, respectively. 1-Semicarbazido-and 1-thiosemicarbazido-3,4-dihydroisoquinolines were shown to undergo thermal elimination of ammonia to give substituted 1,2,4-triazolo[3,4-a]isoquinolin-3-ones and 1,2,4-triazolo[3,4-a]isoquinoline-3-thiones. 1997 Plenum Publishing Corporation.