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Cyanoethylation of 2,5-dimethyltetrahydro-4-thiopyranone isomers and selective reduction of 2,5-dimethyl-5-(β-cyanoethyl)tetrahydro-4-thiopyranone and — 4-pi pe ridone

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It has been found that only the cis isomer (liquid) of 2,5-dimethyltetrahydro-4-thiopyranone is cyanoethylated under the usual conditions. 2,5-Dimethyl-5-(β-carboxyethyl)tetrahydro-4-thiopyranone was synthesized by the acid hydrolysis of 2,5-dimethyl-5-(β-cyanoethyl)-tetrahydro-4-thiopyranone. The selective reduction with aluminum isopropoxide of 2,5-dimethyl-5-(β-eyanoethyl) tetrahydro-4-thiopyranone and of the individual isomers of 2,5-dimethyl-5-(β-cyanoethyl)-4-piperidone gave the isomeric 2,5-dimethyl-5-(β-cyanoethyl)-tetrahydro-4-thiopyranols and -4-piperidols. The reaction of the isomeric 5-cyanoethyl-4-piperidols with allyl bromide gave the corresponding 1-allyl-2,5-dimethyl-5(β-cyanoethyl)-4-piperidols.

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Literature cited

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Authors and Affiliations

  1. Kazakh State University, Alma-Ata

    A. Sh. Sharifkanov, N. A. Bushneva, K. Kh. Tokmurzin & I. S. Chanysheva

Authors
  1. A. Sh. Sharifkanov
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  2. N. A. Bushneva
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  3. K. Kh. Tokmurzin
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  4. I. S. Chanysheva
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 12–14, January, 1972.

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Sharifkanov, A.S., Bushneva, N.A., Tokmurzin, K.K. et al. Cyanoethylation of 2,5-dimethyltetrahydro-4-thiopyranone isomers and selective reduction of 2,5-dimethyl-5-(β-cyanoethyl)tetrahydro-4-thiopyranone and — 4-pi pe ridone. Chem Heterocycl Compd 8, 10–12 (1972). https://doi.org/10.1007/BF00478479

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  • DOI: https://doi.org/10.1007/BF00478479

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