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Synthesis and e/z determination of substituted 2-phenylimidazoles

✍ Scribed by ToméŠ Szotkowski; Filip Bureš; Oldǐich Pytela; Jiǐí Kulhének; Zdeněk Trévníček

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
511 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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.

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