Synthesis and Microbial Evaluation of Versatile Base Catalyzed Chiral Tetrahydrobenzofuran Derivatives via Multicomponent Reaction

Title:Synthesis and Microbial Evaluation of Versatile Base Catalyzed Chiral Tetrahydrobenzofuran Derivatives via Multicomponent Reaction

Volume: 13 Issue: 6

Author(s): Khushal Kapadiya, Rohit Kotadiya, Kishor Kavadia, Ramesh Kothari, Krunal Mehariya and Ranjan Khunt

Affiliation:

Keywords: Tetrahydrobenzofurans, dimedone, multicomponent reactions (MCRs), antimicrobial activity, MIC, XRD study.

Abstract: A base catalyzed sequential one-pot protocol for an effective preparation of 3-(substitutedphenyl) -6,6-dimethyl-2-(substitutedphenylcarbonyl)-3,5,6,7-tetrahydro-1-benzofuran- 4(2H)-one derivatives have been described. One-pot reaction of aromatic aldehydes, various phenacyl bromide and dimedone gives corresponding substituted benzofurans in economically affordable yields with stereo specificity at 2^nd and 3^rd position via formation of substituted pyridinium ylides. Newly synthesized compounds were characterized by different spectral techniques such as IR, ¹H NMR, ¹³C NMR and Mass spectrometry. Furthermore, the structure of compound 4f was unambiguously assigned by X-ray crystallography. All the synthesized compounds were subjected to in-vitro antimicrobial screening against a panel of pathogenic strains of bacteria to evaluate their potency as a MIC. Some of the compounds were found to be equipotent or extra potent than commercial antibiotics against some active strains.

Cite this article as:

Kapadiya Khushal, Kotadiya Rohit, Kavadia Kishor, Kothari Ramesh, Mehariya Krunal and Khunt Ranjan, Synthesis and Microbial Evaluation of Versatile Base Catalyzed Chiral Tetrahydrobenzofuran Derivatives via Multicomponent Reaction, Letters in Drug Design & Discovery 2016; 13 (6) . https://dx.doi.org/10.2174/1570180812666150914220727