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Title: Facile synthesis and fungicidal activity of novel 4,4<i>'</i>-bis[2<i>''</i>-(5<i>'''</i>-substituted rhodanin-3<i>'''</i>-yl)thiazol-4<i>"</i>-yl]bibenzyls<b></b>
Authors: Siddiqui, I R
Singh, Pravin K
Singh, Jaya
Singh, Jagdamba
Keywords: Bibenzyl
microwave irradiation
Knoevenagel condensation
lock and key mechanism
Issue Date: Oct-2005
Publisher: CSIR
Series/Report no.: <b>Int.Cl.<sup>7</sup> C 07 D // A 61 P 31/10</b>
Abstract: Acylation of bibenzyl, followed by reaction with thiourea and I<sub>2</sub> in the presence of NH<sub>3</sub>, yields 4,4<i style="">'</i>-bis(2<i style="">"</i>-aminothiazol-4<i style="">"</i>-yl)bibenzyl <b style="">3</b>. Compound <b style="">3</b>, on treatment with CS<sub>2</sub> in the presence of NH<sub>3</sub> and cyclization with ClCH<sub>2</sub>COONa and HCl, furnishes 4,4<i style="">'</i>-bis[2<i style="">"</i>-(rhodanin-3<i style="">"'</i>-yl)thiazol-4<i style="">"</i>-yl]bibenzyl <b style="">4</b>. Compound <b style="">4</b>, on Knoevenagel condensation with aromatic aldehydes by conventional methods as well as microwave irradiation in the presence of NaCl as catalyst under solvent-free conditions, gives 4,4<i style="">'</i>-bis[2<i style="">''</i>-(5<i style="">'''</i>-substituted rhodanin-3<i style="">'''</i>-yl)thiazol-4<i style="">"</i>-yl]bibenzyls <b style="">5a-p</b>. The reaction rate is enhanced 230 times by using microwave heating with improved yields in comparison with conventional method. All compounds show promising antifungal activity against <i style="">Fusarium oxysporum </i>and <i style="">Penicillium citrinum</i>. Structure-activity relationships for the screened compounds are discussed.
Description: 2102-2106
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(10) [October 2005]

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