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Ringschlußreaktionen von 2-Acyl-1-chlor-enaminen mit thioamidfunktionellen Verbindungen: Wahlweiser Zugang in die 1,3-Thiazin- und 1,3-Oxazin-Reihe

Cyclization reactions of 2-acyl-1-chloro-enamines with thioamide functional compounds: Alternative access to the 1,3-thiazine and 1,3-oxazine series

  • Organische Chemie Und Biochemie
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Abstract

2-Acyl-1-chloro-enamines2 react with thioureas to 2,6-diamino-1,3-thiazinium salts3, following the usual transformation mode of 1-heterosubstituted acylvinylchloridesA. On the other hand the reaction of2 with thiobenzamide preferably leads to 4-amino-1,3-oxazinium salts7. The last course is discussed in terms of imidoyl-migration in the primary productE formingF, which finally undergoes ring condensation. This assumption corresponds in the best way with all experimental findings, moreover with special model reactions (e.g.2 →13).

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Literatur

  1. Schroth W (1985) Khim Geterotsikl Soedin 1985: 1587

    Google Scholar 

  2. Schroth W, Spitzner R, Koch B (1982) Synthesis 1982: 203;

    Google Scholar 

  3. Schroth W, Spitzner R, Koch B, Freitag S, Mielke D (1982) Tetrahedron 38: 937;

    Google Scholar 

  4. vgl. auchSpitzner R, Menzel M, Schroth W (1982) Synthesis 1982: 206;

    Google Scholar 

  5. vgl.Schroth W, Spitzner R, Freitag J (1983) Synthesis 1983: 827

    Google Scholar 

  6. Schroth W, Dill G, Dung NgK, Khoi NgM, Binh Ph, Waskiewicz H-J (1974) Z Chem 14: 52;

    Google Scholar 

  7. Schroth W, Burkhardt U, Thieβ P, Spitzner R (1984) Z Chem 24: 435

    Google Scholar 

  8. Schroth W, Hildebrandt A, Becker U, Freitag S, Akram M, Spitzner R (1985) Z Chem 25: 20

    Google Scholar 

  9. Spitzner R, Mielke D, Scholz D, Schroth W, Preiβ A (1982) Tetrahedron 38: 927

    Google Scholar 

  10. Schroth W, Spitzner R, Hugo S (1982) Synthesis 1982: 199

    Google Scholar 

  11. Schroth W,Richter M,Dobner B,Spitzner R,Freitag S (1987) (Veröffentlichung in Vorbereitung)

  12. Erste Ergebnisse bei:Spitzner R, Schroth W (1976) Mittbl Chem Gesellsch DDR 23: 1 (Vortragsreferat)

    Google Scholar 

  13. Vgl. Übersichten über 1,3-Oxaziniumsalze: a)Schmidt RR (1972) Synthesis 1972: 333;

    Google Scholar 

  14. Kato T, Katagiri N (1980) Heterocycles 14: 1333

    Google Scholar 

  15. Schroth W,Freitag S,Richter M (noch unveröffentlicht)

  16. Vgl. auchSchmidt RR, Schwille D, Sommer S (1969) Liebigs Ann Chem 723: 111

    Google Scholar 

  17. Schroth W, Spitzner R (1987) Monatsh Chem 118: 1263

    Google Scholar 

  18. Woodward RB, Olofson RA (1961) J Am Chem Soc 83: 1007;

    Google Scholar 

  19. Woodward RB, Olofson RA (1966) Tetrahedron [Suppl] 7: 415

    Google Scholar 

  20. Niederhauser A, Bart G, Neuenschwander M (1973) Helv Chim Acta 56: 2427

    Google Scholar 

  21. Vgl. a)Minkin VI, Olechnovich LP, Shdanov JuA, Kiselev VV, Metlushenko VP, Borisenko NI (1974) Zh Org Khim 10: 2248, und dort zit. Lit.;

    Google Scholar 

  22. Wachsen E, Hartke K (1976) Chem Ber 109: 1353, und dort zit Lit.

    Google Scholar 

  23. Vgl. auchHartke K, Wachsen E (1976) Liebigs Ann Chem 1976: 730

    Google Scholar 

  24. Gompper R, Schäfer H (1967) Chem Ber 100: 591, speziell S 601

    Google Scholar 

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Authors and Affiliations

  1. Sektion Chemie, Martin-Luther-Universität Halle-Wittenberg, DDR-4050, Halle (Saale), Deutsche Demokratische Republik

    Roland Spitzner, Sabine Freitag & Werner Schroth

Authors
  1. Roland Spitzner
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  2. Sabine Freitag
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  3. Werner Schroth
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Herrn Prof. Dr.Klaus Hafner zum 60. Geburtstag gewidmet.

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Spitzner, R., Freitag, S. & Schroth, W. Ringschlußreaktionen von 2-Acyl-1-chlor-enaminen mit thioamidfunktionellen Verbindungen: Wahlweiser Zugang in die 1,3-Thiazin- und 1,3-Oxazin-Reihe. Monatsh Chem 118, 1383–1394 (1987). https://doi.org/10.1007/BF00810643

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  • DOI: https://doi.org/10.1007/BF00810643

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