Abstract
The synthesis of 2,2-dimethyl-4-chloromethyl-1,2-dihydro- and -1,2,3,4-tetrahydro-γ-carbolines was developed, and it is shown that the latter undergo rearrangement processes to give 4,4-dimethyl-, 1-piperidino-4,4-dimethyl-, and 1-morpholino-4,4-dimethyl-1, 2,3,4,5,6-hexahydroazepino[4,5-b]indoles, respectively, under the influence of nucleophilic reagents, viz., sodium borohydride, piperidine, and morpholine.
Similar content being viewed by others
Literature cited
R. C. Fuson and C. W. Zorkle, J. Am. Chem. Soc., 70, 2760 (1948).
J. H. Biel, W. K. Hoya, and A. A. Leiser, J. Am. Chem. Soc., 81, 2527 (1959).
N. B. Chapman and D. J. Triggle, J. Chem. Soc., No. 3, 1385 (1963).
J. M. Surzur, L. Stella, and P. Tordo, Bull. Soc. Chim. Fr., No. 1, 115 (1970).
T. B. Zalucky, L. Malspeis, and G. Hite, J. Org. Chem., 29, 3143 (1964).
L. H. Sternbach, J. Med. Chem., 22, 1 (1979).
M. Julia, J. Bagot, and O. Siffert, Bull. Soc. Chim. Fr., No. 4, 1424 (1973).
N. N. Komzolova, N. F. Kucherova, and V. A. Zagorevskii, Zh. Org. Khim., 1, 1139 (1965).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1387–1390, October, 1980.
Rights and permissions
About this article
Cite this article
Zagorevskii, V.A., Novikova, N.N., Kucherova, N.F. et al. Synthesis and transformations of 2,2-dimethyl-4-chloromethyl-1,2,3,4-tetrahydro-γ-carboline. Chem Heterocycl Compd 16, 1054–1057 (1980). https://doi.org/10.1007/BF00496610
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00496610