Abstract
The cyclization of trans-1-acrylyl-4-n-alkylcyclohexanes with trans-1-N-piperidino-1-alkenes was used to synthesize 3-n-alkyl-6-(trans-4-n-alkyl-cyclohexyl)-3,4-dihydro-2-N-piperidino-2H-pyrans, which were converted under the influence of hydroxylamine to 5-n-alkyl-2-(trans-4-n-alkylcyclohexyl)-pyridines. Problems in the stereochemistry of the cyclohexane derivatives in the investigated scheme of synthesis were examined.
Similar content being viewed by others
Literature cited
M. Carissime, Farm. Ed. Sci., 34, 1039 (1979).
C. Botteghi, G. Caccia, and S. Gladiali, Synth. Commun., 9, 69 (1979).
R. Dulou, E. Elkik, and A. Veillard, Bull. Soc. Chim. Fr., No. 5, 967 (1960).
J.-L. Gras, Tetrahedron Lett., No. 32, 2955 (1978).
H. Schubert, V. Uhlig, and R. Dehne, Z. Chem., 12, 219 (1972).
W. Sucrow and H. Wolter, Chimia, 36, 460 (1982).
R. Kh. Geivandov and E. I. Kovshev, Zh. Org. Khim., 15, 218 (1979).
H. Rupe, W. Messner, and E. Kambli, Helv. Chim. Acta, 11, 449 (1928).
M. Kagawa, Chem. Pharm. Bull. (Tokyo), 9, 391 (1961); Chem. Abstr., 55, 24808 (1961).
F. G. Fischer and K. Lowenberg, Ann. Chem., 475, 183 (1929).
A. Gordon and R. Ford, The Chemist's Companion, Wiley (1973).
V. M. Potapov and A. P. Terent'ev, Zh. Obshch. Khim., 28, 3323 (1958).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 643–647, May, 1984.
Rights and permissions
About this article
Cite this article
Pavlyuchenko, A.I., Purvanetskas, G.V., Daukshas, V.K. et al. Synthesis of 5-n-alkyl-2-(trans-4-n-alkylcyclohexyl)pyridines. Chem Heterocycl Compd 20, 515–518 (1984). https://doi.org/10.1007/BF00514304
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00514304