Skip to main content
SpringerLink
Log in

Über 4-Alkylamino-bzw. 4-Arylamino-5,6-dihydro-2(1H)-pyridinthione

4-Alkylamino- and 4-arylamino-5,6-dihydro-2(1H)-pyridinethiones

Über Heterocyclen, 45. Mitt.

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

Abstract

Heating 1-alkyl- or 1-aryldihydro-6-methyl-2(1H)-pyrimidinethiones5, 6 in an inert medium causes rearrangement to 4-alkylamino-(4-arylamino-)-5,6-dihydro-2(1H)-pyridinethiones11, 12, probably via the methylene form29, by thermal heterolysis of the N1/C2 bond and exchange of the alkylamino (arylamino) group 1 through the carbon atom of the methylene group 6. The aminodihydropyridinethiones11, which can be regarded as cyclic derivatives of 3-aminothiocrotonamide, react with bistrichlorophenylmalonate under diacylation, and with formaldehyde and primary amines to yield aminodialkylation products of the enamine system, tetrahydro-4-hydroxy-7,7-dimethyl-5-thioxopyrido[4,3-b]pyridine-2(1H)-ones13, 14 and hexahydro-7,7-dimethylpyrido[4,3-d]pyrimidine-5(6H)-thiones18, 19, 21 respectively. H2O2 converts11 to the corresponding 4-aminodihydro-2(1H)-pyridones22, which can be reconverted into11 with P4S10.11 reacts with alkyl halides to 2-alkylthiodihydropyridines23, 24, 25. The mechanism of the methylpyrimidine-pyridine rearrangement is discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literatur

  1. B. V. Unkovskii undL. A. Ignatova, Khim. Get. Soed.1969, 896.

  2. Vgl. versiegeltes Schreiben, welches am 1. Juni 1973 unter dem Kennwort “Dihydro-2(1H)-pyridinthione” zur Wahrung der Priorität unter der Nr. 1777 bei der Österr. Akademie der Wissenschaften in Wien deponiert wurde.

  3. G. Zigeuner, W. Galatik, W.-B. Lintschinger undF. Wede, Mh. Chem.106, 1219 (1975).

    Google Scholar 

  4. G. Zigeuner, A. Frank, H. Dujmovits undW. Adam, Mh. Chem.101, 1415 (1970).

    Google Scholar 

  5. G. Zigeuner, W.-B. Lintschinger undA. Fuchsgruber, unveröffentlicht; vgl. auch DissertationW.-B. Lintschinger, Univ. Graz 1973.

  6. Zur S-Alkylierung der Dihydropyrimidin-2(1H)-thione vgl. z. B.G. Zigeuner, T. Strallhofer, F. Wede undW.-B. Lintschinger, Mh. Chem.106, 1469 (1975).

    Google Scholar 

  7. G. Zigeuner und Mitarb., unveröffentlicht; vgl. auch DissertationKr. Kollmann, Univ. Graz, 1974.

  8. Vgl. auch Diss.F. Wede, Univ. Graz, 1975.

  9. A. J. Birch, J. chem. Soc.1937, 1270.

  10. R. Lukeš undJ. Jizba, Coll. Czech. Chem. Commun.19, 930, 941 (1954).

    Google Scholar 

  11. D. R. Osborne, W. T. Wieder undR. Levine, J. heterocycl. Chem.1, 145 (1964).

    Google Scholar 

  12. T. L. Cairns, A. W. Larchar undB. C. McKusick, J. Amer. Chem. Soc.74, 5633 (1952).

    Google Scholar 

  13. Vgl.L. J. Bellamy, Ultrarot-Spektrum und chemische Konstitution. Darmstadt: Steinkopf-Verlag. 1966 bzw.L. J. Bellamy, Advances in Infrared Group Frequencies, Methuen, 1968.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Pharmazeutische Chemie der Universität Graz, Universitätsplatz 1, A-8010, Graz, Österreich

    Gustav Zigeuner, W.-Bernd Lintschinger, Alfred Fuchsgruber & Krystyna Kollmann

Authors
  1. Gustav Zigeuner
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. W.-Bernd Lintschinger
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alfred Fuchsgruber
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Krystyna Kollmann
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zigeuner, G., Lintschinger, WB., Fuchsgruber, A. et al. Über 4-Alkylamino-bzw. 4-Arylamino-5,6-dihydro-2(1H)-pyridinthione. Monatshefte für Chemie 107, 155–170 (1976). https://doi.org/10.1007/BF00909092

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00909092

Search

Navigation