Cyclization of Bifunctional 3,5-Diamino-1H-1,2,4-triazole-1-carboximid­amide, 5-Amino-3-hydrazinotriazole and 3,6-Diguanidino-1,2,4,5-tetrazine: A One-Step Route to Fluorinated Heteropolycycles

Abstract

A series of new fluorine-containing triazolylpyrimidines and pyrimidinoaminotetrazines results from one-pot reactions of 3,5-diamino-1H-1,2,4-triazole-1-carboximid­amide hydrochloride and 1,4-diguanidino-2,3,4,5-tetrazine with fluoro-1,3-diketones. Bicyclization of a variety of fluorinated 1,3-diketones gave three fluorinated heterocyclic pyrazolo[1,2,4]triazolo[1,5-a]pyrimidines in moderate yield in a single step.

Key words

cyclization - bifunctional heterocycles - fluorinated polyheterocycles - triazolylpyrimidines - pyrazolo[1,2,4]triazolo[1,5-a]pyrimidines

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SMART: v.5.632, Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, WI, 2005

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SAINTPlus: v. 7.23a, Data Reduction and Correction Program, Bruker AXS, Madison, WI, 2004

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SADABS: v.2004/1, an empirical absorption correction program, Bruker AXS Inc., Madison, WI, 2004

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SHELXTL: v. 6.14, Structure Determination Software Suite, Sheldrick G.M., Bruker AXS Inc., Madison, WI, 2004

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CCDC 666024 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_-_request/cif.