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Russian Chemical Bulletin

, Volume 68, Issue 2, pp 357–364 | Cite as

Utilization of potassium carbonate for the synthesis of 2-(organylsulfonyl)thieno[2,3-b]pyridine derivatives

  • V. E. KaluginEmail author
  • A. M. Shestopalov
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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.

Key words

3-cyanopyridine-2(1H)-thiones methyl 4,6-dimethylpyridine-2(1H)-thione-3-carboxylate chloromethyl organyl sulfones potassium carbonate 2-(organylsulfonyl)- thieno[2,3-b]pyridine-3-amines 4,6-dimethyl-2-(organylsulfonyl)thieno[2,3-b]pyridine-3-oles 4,6-dimethyl-2-(organylsulfonyl)thieno[2,3-b]pyridine-3(2H)-ones 

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Copyright information

© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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