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Synthesis 2010(10): 1645-1648  
DOI: 10.1055/s-0029-1218718
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient Synthesis of 5-Substituted 2-Amino[1,2,4]triazolo[1,5- a][1,3,5]triazin-7(6H)-ones from N-Triazolide Imidates and 1,2,4-Triazole-3,5-diamine

Mehdi Khankischpur, Finn K. Hansen, Detlef Geffken*
Institute of Pharmacy, University of Hamburg, Bundesstr. 45, 20146 Hamburg, Germany
Fax: +49(40)428386573; e-Mail: geffken@chemie.uni-hamburg.de;
Further Information

Publication History

Received 17 December 2009
Publication Date:
26 March 2010 (online)

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Abstract

A convenient and efficient synthesis of previously unreported N-triazolide imidates and their reaction with 1,2,4-triazole-3,5-diamine to give regioselectively 5-substituted 2-amino[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(6H)-ones is described. The structure of the reported bicyclic compounds has been unambiguously proven by X-ray crystallography.

Key words

imidates - heterocycles - cyclizations - triazolotriazines - ring-closure

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CCDC-755847 contains the supplementary crystallographic data for the deposited structure. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Crystal data for compound 4f: Empirical formula: C12H12N6O; Mr = 256.28; Crystal system = monoclinic; Space group P21/n; Unit cell dimensions a = 11.6229(9), b = 9.8793(8), c = 10.1094(8) Å; β = 94.834(3)˚; V = 1156.69(16) ų; T = 100 K; Z = 4; D(calcd) = 1.472 Mg˙m-³; µ = 0.10 mm-¹; λ (Mo K α) = 0.71073 Å; F(000) = 536; 2636 independent reflections (R int = 0.027), 2254 reflections with I > 2s(I); refinement method full-matrix least-squares refinement on F ²; R[F ²>2s(F ²)] = 0.037, wR(F ²) = 0.094, S = 1.05.