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

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.

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Correspondence to V. E. Kalugin.

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Dedicated to Corresponding Member of the Russian Academy of Sciences G. I. Nikishin on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0357–0364, February, 2019.

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Kalugin, V.E., Shestopalov, A.M. Utilization of potassium carbonate for the synthesis of 2-(organylsulfonyl)thieno[2,3-b]pyridine derivatives. Russ Chem Bull 68, 357–364 (2019). https://doi.org/10.1007/s11172-019-2393-7

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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