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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 12, pp 1607–1609 | Cite as

Synthesis of the novel naphtho-[1,2-e][1,2,4]triazolo[5,1-b][1,3]oxazine heterocyclic system

  • V. A. OsyaninEmail author
  • D. V. Osipov
  • Yu. N. Klimochkin
Article
Condensed 1,2,4-triazoles find use in human and veterinary medicine as tranquilizers [ 1], fungicides [ 2], antihistamine [ 3], and antihypertensive [ 4] preparations. In continuing our studies of the synthetic potential of naphthalene series o-quinone methides for the preparation of condensed azolo-1,3-oxazines [ 5] we have carried out a one-stage synthesis of the naphtho[1,2- e][1,2,4]triazolo[5,1- b][1,3]oxazines 2a,b from 3,5-dibromo-1,2,4-triazole and the Mannich base 1b or its quaternized analog 1a in the presence of K 2CO 3. We have also found that derivative 1a in refluxing acetonitrile in the absence of the potassium carbonate selectively formed 1-[(3,5-dibromo-1  H-1,2,4-triazol-1-yl)methyl]-2-naphthol ( 3).

Keywords

3,5-dibromo-1,2,4-triazole o-quinone methides naphtho[1,2-e][1,2,4]triazolo[5,1-b][1,3]oxa- zines Mannich bases 

References

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    C. J. Paget, US Pat. Appl. 3974286.Google Scholar
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    V. Alagarsamy, V. R. Solomon, and M. Murugan, Bioorg. Med. Chem., 15, 4009 (2007).CrossRefGoogle Scholar
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    K.-C. Liu and M.-K. Hu, Arch. Pharm., 319, 188 (1986).CrossRefGoogle Scholar
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    V. A. Osyanin, D. V. Osipov, and Yu. N. Klimochkin, Khim. Geterotsikl. Soedin., 136 (2011). [Chem. Heterocycl. Comp., 47, 108 (2011)].Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • V. A. Osyanin
    • 1
    Email author
  • D. V. Osipov
    • 1
  • Yu. N. Klimochkin
    • 1
  1. 1.Samara State Technical UniversitySamaraRussia

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