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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. Turks
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Abstract


5-Azidotetrazolo[1,5-a]quinazoline (formally known as 2,4-diazidoquinazoline) undergoes regioselective nucleophilic aromatic substitution with amines at 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 diffraction 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.

How to Cite
Kalniņa, A.; Bizdēna, Ē.; Kiselovs, G.; Mishnev, A.; Turks, M. Chem. Heterocycl. Compd. 2014, 49, 1667. [Khim. Geterotsikl. Soedin. 2013, 1797.]

For this article in the English edition see DOI 10.1007/s10593-014-1418-2


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 crystallografy

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