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Synthesis and reactions of 3-cyano-6-methoxymethyl-4-methyl-2(1H)-pyridinethione

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Nucleophilic substitution of the chlorine atom in 2-chloro-3-cyano-6-methoxymethyl-4-methylpyridine by mercapto group produces the corresponding 2(1H)-pyridinethione, alkylation of which by halogenated compounds in the presence of KOH proceeds regioselectively to form S-alkyl derivatives. Thorpe—Ziegler cyclization of S-alkyl derivatives, which contain an active methylene group, yields new 3-aminothieno[2,3-b]-pyridines.

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Authors
  1. E. A. Kaigorodova
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  2. L. D. Konyushkin
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  3. S. N. Mikhailichenko
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  4. V. K. Vasilin
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  5. A. V. Sazonov
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  6. V. G. Kul'nevich
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Additional information

Kuban State Technological University, Krasnodar 350072, Russia, and N. D. Zelinskii Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow 117913; e-mail: stud@issep.rssi.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 337–341, March, 1999.

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Kaigorodova, E.A., Konyushkin, L.D., Mikhailichenko, S.N. et al. Synthesis and reactions of 3-cyano-6-methoxymethyl-4-methyl-2(1H)-pyridinethione. Chem Heterocycl Compd 35, 293–296 (1999). https://doi.org/10.1007/BF02259358

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  • DOI: https://doi.org/10.1007/BF02259358

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