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Synthesis 2008(11): 1775-1782  
DOI: 10.1055/s-2008-1067047
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Zhuo Zeng, Wendell Scott Hyer, Brendan Twamley, Jean’ne M. Shreeve*
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA
e-Mail: jshreeve@uidaho.edu;
Further Information

Publication History

Received 5 February 2008
Publication Date:
29 April 2008 (online)

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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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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.