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*

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