Abstract
The reaction of 3-oxoquinuclidine with ethyl formate in the presence of sodium and with dimethylformamide diethylacetal was used to synthesize 2-hydroxymethylene- and 2-dimethylaminomethylene-3-oxoquinuclidines, which upon reaction with amines from N-substituted 2-aminomethylene-3-oxoquinuclidines and upon reaction with hydrazine hydrate give pyrazolo [3,4-b]quinuclidines. The reaction of 2-aryl- and 2-heteroarylmethylene-3-oxoquinuclidines with hydrazine hydrate and thiourea, which led to the synthesis of pyrazolo[3,4-b]- and pyrimido[5,4-b]quinuclidines with aryl or heteroaryl substituents in the resulting ring, was studied.
Similar content being viewed by others
Literature cited
V. Georgian and W. Koster, Heterocycles, 7, 1017 (1977).
D. R. Bender and D. L. Coffen, J. Org. Chem., 33, 2504 (1968).
V. A. Bondarenko, N. A. Komarova, N. I. Andreeva, T. Ya. Filipenko, K. F. Turchin, E. E. Mikhlina, M. D. Mashkovskii, Yu. N. Sheinker, and L. N. Yakhontov, Khim.-farm. Zh., No. 8, 45 (1979).
V. A. Bondarenko, E. E. Mikhlina, T. Ya. Filipenko, K. F. Turchin, Yu. N. Sheinker, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 10, 1393 (1979).
O. I. Gorbyleva, T. Ya. Filipenko, E. E. Mikhlina, K. F. Turchin, Yu. N. Sheinker, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 6, 793 (1982).
E. J. Warawa and J. R. Campbell, J. Org. Chem., 39, 3511 (1974).
S. Elkin and H. Lieberman, US Patent No. 3726877; Chem. Abstr., 79, 31939 (1973).
T. Ya. Filipenko, O. I. Gorbyleva, K. F. Turchin, O. S. Anisimova, E. M. Peresleni, E. E. Mikhlina, Yu. N. Sheinker, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 5, 666 (1981).
O. I. Gorbyleva, E. E. Mikhlina, T. Ya. Filipenko, K. F. Turchin, O. S. Anisimova, Yu. N. Sheinker, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 3, 407 (1981).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1232–1237, September, 1982.
Rights and permissions
About this article
Cite this article
Gorbyleva, O.I., Filipenko, T.Y., Mikhlina, E.E. et al. Synthesis of 2-hydroxymethylene- and 2-dimethylaminomethylene-3-oxoquinuclidines and their reactions with nucleophilic reagents. Chem Heterocycl Compd 18, 948–954 (1982). https://doi.org/10.1007/BF00513439
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00513439