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On triazoles XIX: The reaction of 5-amino-1,2,4-triazoles with functionalized acetoacetic esters

Über Triazole, 19. Mitt.: Die Reaktion von 5-Amino-1,2,4-triazolen mit funktionalisierten Acetoessigestern

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

Summary

Different “functionalized” alkyl 3-oxo-butyrates (2) were reacted with 5-amino-3-Q-1H-1,2,4-triazoles (1) to yield3 and4 type 1,2,4-triazolo[1,5-a]pyrimidinones. In case of2 (R 1=methyl,R 2=1-ethoxycarbonylethyl,R 3=ethyl) beside the corresponding derivative4 the unexpected 5,6-dihydro-6,8-dimethyl-7-ethoxycarbonyl-3-methylthio-1,2,4-triazolo[4,3-a]-1,3-diazepin-5(9H)-one (7) was isolated, representing a novel ring system.

Zusammenfassung

Verschiedene „funktionalisierte“ 3-Oxo-buttersäurealkylester (2) wurden mit 5-Amino-3-Q-1H-1,2,4-triazolen (1) umgesetzt, wobei 1,2,4-Triazolo[1,5-a]pyrimidinone der Typen3 und4 erhalten wurden. Im Fall von2 (R 1=Methyl,R 2=1-Ethoxycarbonylethyl,R 3=Ethyl) wurde neben dem erwarteten Derivat4 das unerwartete 5,6-Dihydro-6,8-dimethyl-7-ethoxycarbonyl-3-me-thylthio-1,2,4-triazolo[4,3-a]-1,3-diazepin-5(9H)-on (7) isoliert, welches ein neues Ringsystem darstellt.

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References

  1. For Part XVIII see: Reiter J., Rivó E. (1989) J. Heterocycl. Chem.26: 971

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Authors and Affiliations

  1. EGIS Pharmaceuticals, H-1475, Budapest, Hungary

    József Reiter & László Pongó

  2. Institute for Drug Research, H-1325, Budapest, Hungary

    Tamás Somorai & István Pallagi

Authors
  1. József Reiter
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  2. László Pongó
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  3. Tamás Somorai
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  4. István Pallagi
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Reiter, J., Pongó, L., Somorai, T. et al. On triazoles XIX: The reaction of 5-amino-1,2,4-triazoles with functionalized acetoacetic esters. Monatsh Chem 121, 173–187 (1990). https://doi.org/10.1007/BF00809530

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  • DOI: https://doi.org/10.1007/BF00809530

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