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SYNTHESIS OF NOVEL N-ARYL-4-[6-(2-FLUOROPYRIDIN-3-YL)QUINAZOLIN-2-YL]PIPERAZINE-1-CARBOXAMIDE OR -CARBOTHIOAMIDE DERIVATIVES AND THEIR ANTIMICROBIAL ACTIVITY

D. Suresh Babu, Doddaga Srinivasulu, Venkata S. Kotakadi
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Abstract


A series of n

ovel N-aryl-4-[6-(2-fluoropyridin-3-yl)quinazolin-2-yl]-piperazine-1-carboxamide or -carbothioamide derivatives was synthesized by cyclization of 5-bromo-2-fluorobenzaldehyde and guanidine carbonate in the presence of dimethylacetamide followed by treatment with isoamylnitrite and diiodomethane in the presence of copper iodide to afford 6-bromo-2-iodoquinazoline. The latter was treated with piperazine in the presence of triethylamine followed by (2-fluoropyridin-3-yl)boronic acid in the presence of  Pd(PPh3)2Cl2 to afford 6-(2-fluoropyridin-3-yl)-2-(piperazin-1-yl)quinazoline which was further treated with various substituted arylisocyanates and arylisothiocyanates to obtain the title compounds. The chemical structures of the synthesized compounds were confirmed by means of LC-MS, 1H, 13C NMR, IR, and mass spectra and elemental analysis. All the  synthesized compounds were evaluated for their in vitro  antibacterial activity against two Gram-positive and two  Gram-negative bacterial species, as well as two different  strains of antibiotic-resistant E. coli and for antifungal activity  against two fungal strains. Some of the compounds have shown potential antimicrobial activity.

How to Cite
Babu, D. Suresh; Srinivasulu, D.; Kotakadi, V. S. Chem. Heterocycl. Compd. 2015, 51, 60. [Khim. Geterotsikl. Soedin. 2015, 51, 60.]

For this article in the English edition see DOI 10.1007/s10593-015-1660-2

 


Keywords


arylisocyanates; arylisothiocyanates; piperazine; quinazoline; Suzuki coupling; antimicrobial activity

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