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Chemistry of Heterocyclic Compounds

, Volume 46, Issue 9, pp 1148–1150 | Cite as

Synthesis and structure of substituted triazoloquinazolines

  • N. V. PoplevinaEmail author
  • A. A. Kuznetsova
  • A. P. Krivenko
Article

Carbonyl-substituted hydroxycyclohexanones such as diethyl 2-Ar-4-hydroxy-4-methyl-6-oxocyclo-hexane-1,3-dicarboxylates (1) and 3-Ar-2,4-diacetyl-5-hydroxy-5-methylcyclohexanones (2) are commonly used for the construction of condensed systems containing a five-membered heterocycle [1]. There have been only a few examples of the construction of six-membered heterocycles starting from such reagents.

We have studied the reaction of carbonyl-substituted hydroxycyclohexanones 1a-c and 2 with 3-amino-1,2,4-triazole. The presence of several nucleophilic sites in the reagent and their arrangement should be conducive for the annelation of a six-membered heterocycle and generation of systems possessing different types of ring fusion and possessing of the nitrogen atoms at different positions.

Heating equimolar amounts of the reagents at 120-140°C without solvent gave previously unreported triazoloquinazolines: ethyl 6-Ar-5,8-dihydroxy-8-methyl-6,7,8,9-tetrahydro[1,2,4]triazolo[3,4-b]quinazoline-...

Keywords

3-amino-1,2,4-triazole hydroxycyclohexanones hydroxyoxocyclohexanedicarboxylates tri- azoloquinazolines 

References

  1. 1.
    A. P. Krivenko and V. V. Sorokin, Zh. Org. Khim., 35, 357 (1999).Google Scholar
  2. 2.
    M. A. Metwally and M. Abdel-Galil, J. Indian Chem. Soc., 65, 766 (1988).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • N. V. Poplevina
    • 1
    Email author
  • A. A. Kuznetsova
    • 1
  • A. P. Krivenko
    • 1
  1. 1.N. G. Chernyshevskii Saratov State UniversitySaratovRussia

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