Author： Saleh Mohamed Hafez Yehia Abdel-Hay Foad Gad Wagdy
Publisher： Taylor & Francis Ltd
ISSN： 1042-6507
Source： Phosphorus, Sulfur, and Silicon and the Related Elements, Vol.179, Iss.2, 2004-02, pp. : 411-426
Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.
Abstract
Reaction of 3-phenylamino-2-thioxo-3H-quinazolin-4-one (1) with methyl iodide, -chloroethylacetate, and -bromobenzoylacetophenone in methanol in the presence of KOH with heating resulted in alkylation on the sulfur atom to 2-alkyl thio derivatives 2–4, respectively. Treatment of 1 with -bromo--cyanoethylacetate afforded 3-hydroxy-10-oxo-4-phenyl-4H,10H-1-thia-4,4a,9-triaza-anthrancene-2-carbonitrile (5). Reaction of the ester 3 with hydrazine hydrate afforded hydrazide 6. The hydrazide 6 on reaction with benzoylacetone, dibenzoylmethane, and ethyl acetoacetate furnished the corresponding pyrazoles 7 and 8 and pyrazolone 9 respectively. Treatment of 6 with methanolic KOH and carbon disulphide afforded 1,3,4-oxadiazole-2-thione derivative 10. Compound 1 reacted namely with 2,3,4,6-tetra-O-acetyl--D-glucopyranosylbromide, 2,3,4,6-tetra-O-acetyl--D-galactopyranosyl bromide, or with 2,3,4-tri-O-acetyl--D-xylopyranosyl bromide to yield S-glycoside derivatives 11–13, respectively. Oxidation of S-glucoside 11 with H2O2 afforded the corresponding sulphone; 2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosylsulphonyl)-3-phenlyamino-3H-quinazolin-4-one (14). The synthesized compounds have been screened for their antimicrobial activity.
Related content
Access to resources
Recommend
2-Methyl-3-{4-[2-(1
By Arulmurugan Subramaniyan Kavitha Helen P.
Molbank, Vol. 2010, Iss. 3, 2010-09 ,pp. :
Access to resources