Zn(OTf)2-catalyzed three component, one-pot cyclocondensation reaction of some new octahydroquinazolinone derivatives and access their bio-potential

Abstract

An efficient synthesis of some new octahydroquinazolinone derivatives 4a-x by the cyclocondensation reaction of corresponding 2-thi(oxo)-1,2-dihydroquinoline-3-carbaldehyde 1a-e, 1,3-dicarbonyl compounds 2a-b, and substituted urea 3a-c using zinc triflate as a catalyst in refluxing ethanol in high yield is described. The structures of new compounds have been characterized on the basis of elemental analysis, FT-IR, 1 H NMR, 13 C NMR, and mass spectral data. All the synthesized compounds were evaluated for their antimicrobial activities against various microbes. Minimum inhibitory concentration values of all the 24 synthesized compounds were also determined. Some of the synthesized compounds exhibited excellent antimicrobial activity.

Synthesis, characterization and biological activity of some new carbostyril bearing 1H-pyrazole moiety

“…As part of our ongoing research in discovery of new active antimicrobial compounds (Makawana et al, 2011;Ladani et al, 2009aLadani et al, , b, 2010Mungra et al, 2009Mungra et al, , 2011Nirmal et al, 2009Nirmal et al, , 2010Shah et al, 2009a, b;Shah and Patel, 2011;Thakor et al, 2008;Patel, 2009a, b, 2011), in this article, we try to study the influence of carbostyril moiety and pyrazole scaffold combination on the antimicrobial effect. So we report herein the synthesis of some new derivatives of 4-pyrazolyl-N-arylquinoline-2,5-dione 4a-p through MCR approach.…”

Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties

“…Shah and Patel synthesized new octahydroquinazolinone derivatives, using a modified Biginelli synthesis ( Scheme 11 ) and a Lewis acid, zinc triflate, as catalyst [ 80 ]. Compounds 35a – 35m were screened for their antibacterial activity against Bacillus subtilis MTCC 441, Clostridium tetani MTCC 449, Streptococcus pneumoniae MTCC 1936, E. coli MTCC 443, Salmonella typhi MTCC 98, and Vibrio cholerae MTCC 3906 as well as for antifungal activity against Aspergillus fumigatus MTCC 3008 and Candida albicans MTCC 227.…”

Silty Clay-Containing Soil Catalyzed Microwave Assisted Multicomponent Synthesis of Octahydroquinazolinone Derivatives

“…Octahydroquinazolinone derivatives is an important class of organic compounds because of their pharmacological activities such as antihypertensive, 1 antibacterial, 2,3 antitumor, 4 anti-inflammatory etc. 5 Multicomponent reactions (MCRs) have apparently been a route to the synthesis of large number of complex molecules from readily available building blocks.…”

“…6 Octahydroquinazolinones synthesis is a modified Biginelli reaction. 1 Octahydroquinazolinone have been synthesized using aromatic aldehydes, dimedone and urea/thiourea in presence of various catalysts such as montmorillonite, 7 zeolites, 8 boron compounds, 9 Zn(OTf)2, 3 conc. H2SO4, 10 ionic liquids, 11 ion exchange resins, 12 Trimethyl silyl chloride, 13 Nafion-H, 14 VOSO4, 15 conc.…”