SYNTHESIS AND PROPERTIES OF SUBSTITUTED ISOXAZOLO[3',4':4,5]THIENO[2,3-<i>b</i>]PYRIDINES

Authors

  • В. К. Василин Kuban State Technological University, Krasnodar 350072
  • Е. А. Кайгородова Kuban State Technological University, Krasnodar 350072
  • С. И. Фирганг N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991
  • Г. Д. Крапивин Kuban State Technological University, Krasnodar 350072

Keywords:

3-aminothieno[2,3-b]pyridines, 3-azidothieno[2,3-b]pyridines, isoxazolo[3',4':4,5]thieno[2,3-b]pyridines, 2-(2-R-ethylthio-2-oxo)-3-pyridyl cyanides, 3-cyano-2(1H)pyridinethiones

Abstract

We synthesized derivatives of a novel heterocyclic system, isoxazolo[3',4':4,5]thieno[2,3-b]pyridine by sequential conversions in three steps: isomerization of 2-(2-R-ethylthio-2-oxo)-3-pyridyl cyanides obtained by alkylation from substituted 3-cyano-2(1H)-pyridinethiones by α-halomethyl ketones in alkaline medium, to form 3-aminothieno[2,3-b]pyridines; diazotization of the amino group followed by nucleophilic substitution of the diazonium group by an azido group, bypassing the step of isolating the diazonium salts; and thermolysis of the azides formed.

How to Cite
Vasilin, V. K.; Kaigorodova, E. A.; Firgang, S. I.; Krapivin, G. D. Chem. Heterocycl. Compd. 2004, 40, 377. [Khim. Geterotsikl. Soedin. 2004, 462.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000028636.31350.c0

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Published

2004-03-25

Issue

No. 3 (2004)

Section

Original Papers