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Title: Facile synthesis and fungicidal activity of novel 4,4'-bis[2''-(5'''-substituted rhodanin-3'''-yl)thiazol-4"-yl]bibenzyls
Authors: Siddiqui, I R
Singh, Pravin K
Singh, Jaya
Singh, Jagdamba
Keywords: Bibenzyl;thiazole;rhodanine;fungicide;microwave irradiation;Knoevenagel condensation;lock and key mechanism
Issue Date: Oct-2005
Publisher: CSIR
IPC Code: Int.Cl.7 C 07 D // A 61 P 31/10
Abstract: Acylation of bibenzyl, followed by reaction with thiourea and I2 in the presence of NH3, yields 4,4'-bis(2"-aminothiazol-4"-yl)bibenzyl 3. Compound 3, on treatment with CS2 in the presence of NH3 and cyclization with ClCH2COONa and HCl, furnishes 4,4'-bis[2"-(rhodanin-3"'-yl)thiazol-4"-yl]bibenzyl 4. Compound 4, 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'-bis[2''-(5'''-substituted rhodanin-3'''-yl)thiazol-4"-yl]bibenzyls 5a-p. 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 Fusarium oxysporum and Penicillium citrinum. Structure-activity relationships for the screened compounds are discussed.
Page(s): 2102-2106
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(10) [October 2005]

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