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
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).


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 


  1. 1.
    M. Negwer, Organic Chemical Drugs and Their Synonyms, 6th edition, Akademie-Verlag, Berlin (1987).Google Scholar
  2. 2.
    C. J. Paget, US Pat. Appl. 3974286.Google Scholar
  3. 3.
    V. Alagarsamy, V. R. Solomon, and M. Murugan, Bioorg. Med. Chem., 15, 4009 (2007).CrossRefGoogle Scholar
  4. 4.
    K.-C. Liu and M.-K. Hu, Arch. Pharm., 319, 188 (1986).CrossRefGoogle Scholar
  5. 5.
    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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