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KMID : 0043319900130040351
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Archives of Pharmacal Research
1990 Volume.13 No. 4 p.351 ~ p.354
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Benzoin in Heterocyclic Synthesis: Synthesis and Reactions of 2,3-Diphenyl-4-cyanopyrrole-5-thione
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Khalifa FA
Zohdi HF/Ibrahim MKA/Ismail NA
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Abstract
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2,3-Diphenyl-4-cyano-pyrrole-5-thione (4) was prepared either by the reaction of benzoin (1) and cyanothioacetamide (3) followed by cycilzation using AcOH/sodium acetate or by refluxing a mixture of benzoin (1) and cyanothioacetamide in pyridine to afford directly 4. Several new pyrrole and pyrazole derivatives were synthesised using 4 as synthon. The structure of the newly synthesised derivatives were based on celemental and spectral data studies. Methylation of the SH group in 4 afforded 5. Reaction of 4 with ethyl bromo acetate afforded (6). Treatment of (5) and (6) with hydrazine hydrate afforded the same pyrazole derivative (10) through the intermediate (9). Treatment of 6 with aniline and phenythydrazine afforded the pyrrole derivatives 8a,b respectively. Treatment of 6 while dil HCl gave 2,3-diphenyl-4-cyano-pyrrole-5-one (7). Treatment of 6 with NH3/EtOH afforded the amidic derivatives (11) with treatment of 6 with NH3/heat then acidification it gave the carboxylic derivatives (12).
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