WATER MEDIATED DIELS-ALDER [4+2] CYCLOADDITION REACTION: A GREEN CHEMICAL APPROACH FOR THE SYNTHESIS OF SOME 2-(6-METHOXY-2-NAPHTHYL)-3-(SUBSTITUTED PHENYL) BICYCLO [2.2.1] HEPTA-5-ENE-2-ONES AND EVALUATION OF BIOLOGICAL ACTIVITIES
Journal Title: Mintage journal of pharmaceutical and medical sciences - Year 2017, Vol 6, Issue 2
Abstract
Objective: To synthesis some 2-(6-methoxy-2-naphthyl)-3-(substituted phenyl) bicyclo[2.2.1] hepta-5-ene ketones and evaluation of their biological activities. Methods: Green chemical approach of water mediated fly-ash catalyzed Diels-Alder[4+2] cycloaddition reaction of E-(6-methoxy-2-naphthyl)-2-propen-1-ones and cyclopentadiene under cooling condition was employed for the synthesis of the Diels-Alder adducts. Analytical and spectral data have been used for characterization of the synthesized ketones. The antimicrobial activities of all ketones were studied using Bauer-Kirby disc diffusion as well as serial dilution methods. The antioxidant activities of all adducts were evaluated by DPPH radical scavenging activity. Results: This fly-ash catalyzed Diels-Alder [4+2] cycloaddition reaction more than 60% yields. All compounds show antimicrobial and antioxidant activities. Conclusion: This water mediated fly-ash catalyzed Diels-Alder[4+2] cycloaddition reaction of E-(6-methoxy-2-naphthyl)-2-propen-1-ones and cyclopentadiene under cooling condition was feasible. Analytical and spectroscopic data have been supported for all synthesized adducts. The methanone derivative possesses halogens, dimethylamino, nitro, methyl, amino, and H substituents were shown better and good antibacterial activity. The substituents nitro, amino, dimethylamino, parent and methoxy present in methanones have shown excellent, better and good antifungal activities against their fungal strains. The compounds containing hydroxy and methoxy substituents showed significant antioxidant activity against DPPH.
Authors and Affiliations
G THIRUNARAYANAN
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