Abstract
By the interaction of a 4-R-cyclohe.xylidenecyanoacetic ester with cyanothio(seleno)acetainide, 6-oxo-3, 5dicyano-1, 4, 5, 6-tetrahydrospiro-(4′-R-cyclohexane-1 ', 4-pyridine)-2-thiols and -selenols have been obtained; these have also been synthesized from a cyclohexytidenecyanothioacetamide and cyanoacetic ester. These thiols and selenols have been used to prepare the corresponding disulfides, diselenides, and spiro systems, including the fragments alkylthio(seleno)tetrahydropyridine, thieno[2, 3-bjpyridine, and 2, 3-dihydrothiazolopyridine.
Similar content being viewed by others
References
G. Guillaumet, T. Podona, G. Adam, B. Guardiola, and P. Renarol, Eur. Pat. Appl. EP 564,358; Chem. Abstr.,120, 1,640,05d (1994).
G. Guillaumet, J. Pharm. Belg.,49, No. 3, 216 (1994).
U.S. Pat. 5185329.
Y. Xu, Z. Zhu, Z. Tong, D. Peng, and Z. Duan, Zhongguo Yiyao Zazhi,24, No. 2, 49 (1993; Chem. Abstr., 120, 8556c (1994).
V. V. Kuznetsov, Khim. Farm. Zh., No. 7, 61 (1991).
U.S. Pat. 4,652,564.
FRG Pat. 3,844,355.
V. P. Litvinov, L. A. Rodinovskaya, Yu. A. Sharanin, A. M. Shestopalov, and A. Senning, Sulfur Rep.,13, No. l, 1 (1992).
V. D. Dyachenko and Yu. A. Sharanin, Zh. Obshch. Khim.,61, 948 (1991).
V. N. Nesterov, V. E. Shklover, Yu. T. Struchkov, Yu. A. Sharanin, A. M. Shestopalov, and L. A. Rodinovskaya, Acta Crystallogr.,41, 1191 (1985).
S. Patai and Z. Rappoport (eds.), The Chemistry of Triple-Bonded Functional Groups, Wiley, New York (1983), p. 107.
Additional information
T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011, Ukraine. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9 pp. 1235–1242, September, 1996. Original article submitted May 13, 1996.
Rights and permissions
About this article
Cite this article
Dyachenko, V.D., Mitroshin, A.E. & Litvinov, V.P. Synthesis and properties of 6-oxo-3,5-dicyano-1,4,5,6tetrahydrospiro-(4′-r-cyclohexane-1′,4-pyridine)-2thiols and -selenols. Chem Heterocycl Compd 32, 1058–1065 (1996). https://doi.org/10.1007/BF01164713
Issue Date:
DOI: https://doi.org/10.1007/BF01164713