Stereoselective synthesis and alkylation of N-methylmorpholinium 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy- 5-(2-thenoyl)-6-trifluoromethyl- 1,4,5,6-tetrahydropyridine-2-thiolate. Molecular and crystal structure of 4,5-trans-4-(2-chlorophenyl)-3-cyano- 6-hydroxy-2-methallylthio-5-(2-thenoyl)- 6-trifluoromethyl-1,4,5,6-tetrahydropyridine

被引:0
作者
Krivokolysko S.G. [1 ]
Dyachenko V.D. [1 ]
Chernega A.N. [2 ]
Litvinov V.P. [3 ]
机构
[1] Taras Shevchenko Lugansk State Pedagogical University
[2] Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev
[3] N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
关键词
2-chlorobenzaldehyde; 2-thenoyltrifluoroacetone; Alkylation; Condensation; Cyanothioacetamide; Tetrahydropyridines;
D O I
10.1023/A:1013889208646
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摘要
The condensation of 2-chlorobenzaldehyde with cyanothioacetamide and 2-thenoyltrifluoroacetone in the presence of N-methylmorpholine takes place stereoselectively and leads to the formation of N-methylmorpholinium 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-5-(2-thenoyl) -6-trifluoromethyl-1,4,5,6-tetrahydropyridine-2-thiolate. The latter was used to synthesize the corresponding 2-alkylthiotetrahydropyridines. The structure of 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-2- methallylthio-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine was determined by X-ray crystallographic analysis.
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页码:1208 / 1215
页数:7
相关论文
共 11 条
  • [1] Litvinov V.P., Dyachenko V.D., Dokl. Akad. Nauk., 352, (1997)
  • [2] Litvinov V.P., Izv. Akad. Nauk, Ser. Khim., (1998)
  • [3] Vereshchagin A.N., Usp. Khim., 52, (1983)
  • [4] Krivokolysko S.G., Dyachenko V.D., Rusanov E.B., Litvinov V.B., Khim. Geterotsikl. Soedin., (2001)
  • [5] Alder R.W., Goode N.C., King T.J., Mellor J.M., Miller B.W., J. Chem. Soc. Chem. Commun., 5, (1976)
  • [6] Burke-Laing M., Laing M., Acta Crystallogr. (B), 32, (1976)
  • [7] Gilli P., Bertolasi V., Ferretti V., Gilli G., J. Am. Chem. Soc., 116, (1994)
  • [8] Kuleshova L.N., Zorkii P.M., Acta Crystallogr. (B), 37, (1981)
  • [9] Watkin D.J., Prout C.K., Carruthers J.R., Betteridge P.W., Crystals, 10, (1996)
  • [10] North A.C.T., Phillips D.C., Scott F., Mathews F.S., Acta Crystallogr. (A), 24, (1968)