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Structural studies of 2‐methyl‐7‐substituted pyrazolo[1,5‐ a ]pyrimidines
Author(s) -
Frizzo Clarissa P.,
Martins Marcos A.P.,
Marzari Mara R. B.,
Campos Patrick T.,
Claramunt Rosa M.,
García M. Ángeles,
Sanz Dionisia,
Alkorta Ibon,
Elguero José
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.377
Subject(s) - chemistry , pyrimidine , intermolecular force , halogen , solid state , trifluoromethyl , nuclear magnetic resonance spectroscopy , computational chemistry , stereochemistry , medicinal chemistry , organic chemistry , molecule , alkyl
ix 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‐trifluoromethylpyrazolo[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. J. Heterocyclic Chem., (2010).