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Synthese des 4-Hydroxy-6,6-dimethyl-5,6-dihydro-2H-thiopyran-2-thions bzw. -ons und der entsprechenden Tautomeren

Syntheses of 4-hydroxy-6,6-dimethyl-5,6-dihydro-2H-thiopyran-2-thione resp.-one and the corresponding tautomers

Über Heterocyclen, 69. Mitteilung

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

The tautomers 4-hydroxy-6,6-dimethyl-5,6-dihydro-2H-thiopyran-2-thione (4 a) and 2-mercapto-6,6-dimethyl-5,6-dihydro-4H-thiopyran-4-one (4 b) resp. were synthesized by hydrolysis of 4-amino-5,6-dihydro-2H-thiopyranthiones6,8. On methylation of4 a,b only the S-methyl product7 is formed. Hydrolysis of 4-amino-2-methylthiothiopyranyliden iodides11 leads—depending on the amino group of11—either to the thiopyranone7 or to the 4-imino-thiopyranes12 and to β-amino-α,β,γ,δ-unsaturated-methyldithio carboxylates13. On reaction of4 a,b with hydrogenperoxyd the tautomers 4-hydroxy-5,6-dihydro-2H-thiopyran-2-one5 a and 5,6-dihydro-2H-thiopyran-2,4(3H)diones5 b resp. are formed.4 a,b and5 a,b undergo an aminolysis with prim. and sec. amines to the corresponding 4-amino-2H-thiopyran-2-thiones6,8 and -ones10 resp. On heating in alcohols the 4-alkoxy-thiopyrane-2-thiones and -ones9,14 are formed from4 a,b and5 a,b resp.

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  1. Institut für Pharmazeutische Chemie, Karl-Franzens-Universität Graz, A-8010, Graz, Österreich

    Klaus Schweiger

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  1. Klaus Schweiger
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Schweiger, K. Synthese des 4-Hydroxy-6,6-dimethyl-5,6-dihydro-2H-thiopyran-2-thions bzw. -ons und der entsprechenden Tautomeren. Monatsh Chem 113, 1283–1297 (1982). https://doi.org/10.1007/BF00808744

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  • DOI: https://doi.org/10.1007/BF00808744

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