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Synthesis and e/z determination of substituted 2‐phenylimidazoles
Author(s) -
Szotkowski ToméŠ,
Bureš Filip,
Pytela Oldǐich,
Kulhének Jiǐí,
Trévníček Zdeněk
Publication year - 2006
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.5570430623
Subject(s) - chemistry , methylene , aldol condensation , stereospecificity , molecule , double bond , condensation , hydrogen bond , pentane , stereochemistry , condensation reaction , crystallography , crystal structure , medicinal chemistry , catalysis , polymer chemistry , organic chemistry , physics , thermodynamics
Nine new 4‐substituted 2‐phenylimidazole derivatives have been synthesized by aldol condensation of 2‐phenylimidazole‐4‐carbaldehyde with various active methylene compounds. In case of non‐symmetric active methylene compound used, the stereospecific formation of only one cis‐trans isomer has been observed. The predominant formation of products with bulkier substituents standing opposite on double bond formed by aldol condensation has been proved. cis‐trans Isomerism of three unsymmetrically substituted products has been determined by 1 H coupled 13 C NMR experiments. 3‐[(2‐Phenylimidazol‐4‐yl)methylene]pentane‐2,4‐dione has been characterized by single crystal X‐ray structural analysis as well. Selected bond lengths and angles have proved the expected large mesomerical stabilisation in the molecule. The hydrogen bond in crystal phase has been observed.