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Wiley, Journal of Heterocyclic Chemistry, 6(47), p. 1259-1268, 2010

DOI: 10.1002/jhet.377

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Structural Studies of 2-Methyl-7-substituted Pyrazolo[1,5-a]pyrimidines

Journal article published in 2010 by Clarissa P. Frizzo ORCID, M. Ángeles García, Marcos A. P. Martins ORCID, Mara R. B. Marzari, Patrick T. Campos, Rosa M. Claramunt, M. Ángeles García, Dionisia Sanz ORCID, Ibon Alkorta ORCID, José Elguero
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Six pyrazolo[1,5-a]pyrimidines bearing a 7-trifluoromethyl (three compounds), a 7-trichloromethyl (two compounds), and a 7-ethoxycarbonyl (one compound) have been structurally characterized. The new X-ray structures of 2-methyl-5-(p-bromophenyl)-7-trifluoromethylpyrazolol[1,5-a]pyrimidine (3) and 2-methyl-7-trichloromethylpyrazolo[1,5-a]pyrimidine (4) are reported. The combined use of GIAO/B3LYP/6-311++G(d,p) calculations with NMR spectroscopy in solution and in the solid state allows to establish some general rules that can be useful for characterizing related compounds. Compounds 3 and 4 present in the solid-state interesting intra- and intermolecular halogen bonds.