REACTION OF DICHLOROCARBENE WITH SUBSTITUTED 3,4-DIHYDROISOQUINOLINES AND 1-METHYLENE-1,2,3,4-TETRAHYDROISOQUINOLINES

Article abstract of DOI:10.1007/BF00480869

Reaction of dichlorocarbene with 3,3-dialkyl-3,4-dihydroisoquinolines results in the formation of gem-dichloroazirino<2,1-a>isoquinolines, which are in turn converted to 3-benzazepinones upon hydrolysis.Reaction of dichlorocarbene with the ethyl ester or amide of (3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)acetic acid is accompanied by rearrangement of the intermediate carbene adducts at the enamine C=C bond and results in the formation of a 1-azadiene, 3-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-3-chloroacrylic acid ethyl ester, and a spirolactam, 3,3-dimethyl-3-chlorospiro<1,2,3,4-tetrahydroisoquinoline-1,2'-pyrrole>-5'(2'H)- one, respectively.