Synthesis and Properties of Substituted Isoxazolo[3',4':4,5]thieno[2,3-b]pyridines |
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| Authors: | V. K. Vasilin . A. Kaigorodova S. I. Firgang G. D. Krapivin |
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| Affiliation: | (1) Kuban State Technological University, Krasnodar, 350072, Russia;(2) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991 |
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| 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  -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. |
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| 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 |
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