IngentaConnect Synthesis and Antimicrobial Activity of Some New 1,3-Diphenylpyra...

Authors: El-Emary, T.¹; Abdel-Mohsen, Sh.¹

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Volume 181, Number 11, November 2006 , pp. 2459-2474(16)

Publisher: Taylor and Francis Ltd

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Abstract:

1,3-diphenyl-1H-pyrazole-4-carboxaldehyde ( 1 ) reacted with ethyl cyanoacetate and thiourea to give the pyrimidinethione derivative 2 . The reaction of 2 with some alkylating agents gave the corresponding thioethers 3a-e and 7 . Thione 2 was cyclized to 5 and 6 upon a reaction with chloroacetic acid and with benzaldehyde, respectively. Thioether 3c was cyclized to 4 upon boiling with sodium acetate in ethanol, and 7 was cyclized to 8 upon boiling in an acetic anhydride-pyridine mixture. The hydrazino derivative 9 was prepared either by boiling 2 and/or 3a with hydrazine. The reaction of 9 with nitrous acid, acetylacetone, triethyl orthoformate, acetic anhydride, and carbon disulfide gave 10-14 . The alkylation of 14 with ethyl iodide, phenacyl bromide, and ethyl chloroacetate afforded the alkythiotriazolo pyrimidinone derivatives 15a-c . The dialkyl derivative 16 was produced upon the treatment of 2 with two equivalents of ethyl iodide. Boiling 16 with hydrazine afforded the hydrazino 17 . The reaction of 17 with nitrous acid, carbon disulfide, ethyl cyanoacetate, ethyl acetoacetae, and phenacyl bromide gave 18-22 , respectively. Some of the newly obtained compounds were tested for their antibacterial and antifungal activities.

Keywords: 1,3-diphenylpyrazole; pyrimidine; pyrimidinethione; thiazolopyrimidine; thio-and alkylthiotriazolpyrimidinone; triazolopyrimidine

Document Type: Research article

DOI: 10.1080/10426500600754695

Affiliations: 1: Chemistry Department, Assiut University, Assiut, Egypt

Synthesis and Antimicrobial Activity of Some New 1,3-Diphenylpyrazoles Bearing Pyrimidine, Pyrimidinethione, Thiazolopyrimidine, Triazolopyrimidine, Thio-and Alkylthiotriazolop-Yrimidinone Moieties at the 4-Position