Utilization of potassium carbonate for the synthesis of 2-(organylsulfonyl)thieno[2,3-b]pyridine derivatives
- Authors: Kalugin V.E.1, Shestopalov A.M.1
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Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Issue: Vol 68, No 2 (2019)
- Pages: 357-364
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/243254
- DOI: https://doi.org/10.1007/s11172-019-2393-7
- ID: 243254
Cite item
Abstract
A novel preparative method for the synthesis of 2-(organylsulfonyl)thieno[2,3-b]pyridine derivatives has been developed, which allows one to obtain the desired products in a good yield and to shorten the reaction duration. The reaction of 3-cyanopyridine-2(1H)-thiones with chloromethyl organyl sulfones in the presence of potassium carbonate as the base gave 2-(organylsulfonyl) thieno[2,3-b]pyridine-3-amines. The same reaction of methyl 4,6-dimethylpyridine- 2(1H)-thione-3-carboxylate with chloromethyl organyl sulfones resulted in tautomeric mixtures of 4,6-dimethyl-2-(organylsulfonyl)thieno[2,3-b]pyridine-3-oles and 4,6-dimethyl-2-(organylsulfonyl) thieno[2,3-b]pyridine-3(2H)-ones.
About the authors
V. E. Kalugin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Author for correspondence.
Email: vek@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
A. M. Shestopalov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: vek@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991