Abstract
Reaction of dichlorocarbene with 3,3-dialkyl-3,4-dihydroisoquinolines results in the formation of gemdichloroazirino[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.
Similar content being viewed by others
Literature Cited
N. S. Zefirov, I. V. Kazimirchik, and K. A. Lukin, Cycloaddition of Dichlorocarbene to Olefins [in Russian], Nauka, Moscow (1985).
U. K. Pandit, Heterocycles, 8, 609 (1977).
R. R. Kostikov and A. F. Khlebnikov, Khim. Geterotsikl. Soedin., No. 11, 1443 (1976).
W. Kirmse, Carbene Chemistry [Russian translation], Mir, Moscow (1966).
R. E. Brooks, J. O. Edwards, G. Levey, and F. Smith, Tetrahedron, 22, 1279 (1966).
K. Ichimura and M. Ohta, Bull. Chem. Soc. Jpn., 40, 1933 (1967).
R. R. Kostikov, A. F. Khlebnikov, and K. A. Ogloblin, Zh. Org. Khim., 9, 2346 (1973).
T. Saraie, I. Ishiguro, K. Kawashima, and K. Morita, Tetrahedron Lett., No. 23, 2121 (1973).
G. Hölfe, Z. Naturforsch., B28, 831 (1973).
H. P. Soetens and U. K. Pandit, Rec. Trav. Chim., 99, 271 (1980).
C. D. Perchonock, I. Lantos, J. A. Finkelstein, and K. G. Holden, J. Org. Chem., 45, 1950 (1980).
I. Lantos, D. Bhattachiriee, and D. S. Eggleston, J. Org. Chem., 51, 4147 (1986).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1086–1091, August, 1990.
Rights and permissions
About this article
Cite this article
Khlebnikov, A.F., Kostikov, R.R., Shklyaev, V.S. et al. Reaction of dichlorocarbene with substituted 3,4-dihydroisoquinolines and 1-methylene-1,2,3,4-tetrahydroisoquinolines. Chem Heterocycl Compd 26, 909–913 (1990). https://doi.org/10.1007/BF00480869
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00480869