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Synthese und Reaktionsverhalten von 6-sec-Amino-1,3-thiazin-2-thionen

Synthesis and chemical behaviour of 6-sec-amino-1,3-thiazine-2-thiones

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

Abstract

The title compounds3 have been prepared by ring transformation reactions of the isomeric 2-sec-amino-1,3-thiazine-6-thiones1 via ring-opening products2 and by special cyclocondensation reactions with thiocarboxamides8, and with iminium salts10, starting from 2,2-dichlorovinyl ketones6 in all cases. The pathways differ specifically in scope and limitations. On the other hand the intermediates2 react with alkylating agents to 2,6-di-sec-amino-1,3-thiazinium salts4, which are also available via alkylation of3 to 2-methylthio-1,3-thiazinium salts11 and aminolysis. Moreover,11 serve as useful precursors for other 1,3-thiazine derivatives by nucleophilic methylthio displacement (examples12).

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Literatur

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  7. Schroth W, Spitzner R, Freitag S, Richter M, Dobner B (1986) Synthesis: 916

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

  9. In der Formulierung für2 bleibt die Möglichkeit einer intramolekularen [N,S]-H-Brückenbindung unberücksichtigt (vgl. IR-Absorption bei 2 700–3 000 cm−1)

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  14. Detaillierte Ergebnisse von vergleichenden Untersuchungen werden später mitgeteilt

  15. Umfangreiche analoge Reaktionen wurden auch mit 6-Organylthio-1,3-thiaziniumsalzen durchgeführt:Schroth W,Richter M,Freitag S,Spitzner R (1987) Publikation in Vorbereitung

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Authors and Affiliations

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

    Werner Schroth, Monika Richter, Bodo Dobner, Roland Spitzner & Sabine Freitag

Authors
  1. Werner Schroth
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  2. Monika Richter
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  3. Bodo Dobner
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  4. Roland Spitzner
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  5. Sabine Freitag
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Schroth, W., Richter, M., Dobner, B. et al. Synthese und Reaktionsverhalten von 6-sec-Amino-1,3-thiazin-2-thionen. Monatsh Chem 119, 463–476 (1988). https://doi.org/10.1007/BF00810427

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  • DOI: https://doi.org/10.1007/BF00810427

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