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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 11, pp 1667–1673 | Cite as

Structural Proof of Tetrazolo[1,5-a]quinazoline Derivatives and their Application in the Synthesis of 4-Amino-2-(1,2,3-triazol-1-yl)quinazolines*

  • A. Kalniņa
  • Ē. Bizdēna
  • G. Kiselovs
  • A. Mishnev
  • M. TurksEmail author
Article

5-Azidotetrazolo[1,5-a]quinazoline (formally known as 2,4-diazidoquinazoline) undergoes regio-selective nucleophilic aromatic substitution with amines at the C-5 atom and provides corresponding 5-amino derivatives of tetrazolo[1,5-a]quinazoline. For the first time, the molecular structure of the latter tricyclic system is unambiguously proved by X-ray structural analysis. Tautomeric equilibrium between tetrazolo[1,5-a]quinazolines and 2-azidoquinazolines permits their use in the copper- catalyzed azide–alkyne 1,3-dipolar cycloaddition reaction. In this way a series of 4-(R-amino)-2-(1,2,3-triazol-1-yl)quinazolines were obtained.

Keywords

4-amino-2-(1,2,3-triazol-1-yl)quinazoline tetrazolo[1,5-a]quinazoline azide–alkyne 1,3-dipolar cycloaddition reaction azide–tetrazole equilibrium X-ray structural analysis 

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • A. Kalniņa
    • 1
  • Ē. Bizdēna
    • 1
  • G. Kiselovs
    • 2
  • A. Mishnev
    • 2
  • M. Turks
    • 1
    Email author
  1. 1.Riga Technical UniversityRigaLatvia
  2. 2.Latvian Institute of Organic SynthesisRigaLatvia

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