SYNTHESIS AND PROPERTIES OF 7-ACETYL-8-ARYL-9-CYANO-3-HYDROXY-6-METHYL-3,4-DIHYDRO-2H,8H-PYRIDO[2,1-<i>b</i>][1,3]THIAZINES

Authors

  • А. Краузе Latvian Institute of Organic Synthesis, Riga LV-1006
  • Л. Силе Latvian Institute of Organic Synthesis, Riga LV-1006
  • P. Дaнне Latvian Institute of Organic Synthesis, Riga LV-1006
  • Г. Дубурс Latvian Institute of Organic Synthesis, Riga LV-1006

DOI:

https://doi.org/10.1007/8199

Keywords:

2-alkylthio-1, 4-dihydropyridines, 1, 4-dihydropyridine-2(3H)-thiones, 3, 4-dihydro-2H, 8H-pyrido[2, 1-b][1, 3]thiazines, epichlorohydrin, amination, acylation

Abstract

7-Acetyl-8-aryl-2-(1-chloro-2-hydroxy-3-propyl)thio-9-cyano-6-methyl-1,4-dihydropyridines were obtained by treatment of 1,4-dihydropyridine-2(3H)-thiones with epichlorohydrin in the presence of sodium bicarbonate. When treated with NaOMe, these compounds are readily intramolecularly alkylated with formation of 7-acetyl-8-aryl-3-hydroxy-9-cyano-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b]-[1,3]thiazines. We have studied amination  of 2-(1-chloro-2-hydroxy-3-propyl)thio-1,4-dihydropyridines and acylation of 3-hydroxy-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines.

How to Cite
Krauze, A.; Sile, L.; Danne, R.; Duburs, G.  Chem. Heterocycl. Compd. 2005, 41, 1189. [Khim. Geterotsikl. Soedin. 2005, 1394.]

For this article in the English edition, see DOI 10.1007/s10593-005-0302-5


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Published

2023-10-25

Issue

No. 9 (2005)

Section

Original Papers