Abstract
Background: Indolizine pharmacophore is known to exhibit various promising pharmacological properties such as analgesic, anticancer, antihistaminic, antidiabetic, anti-inflammatory, antileishmanic, antimicrobial, antimutagenic, antioxidant, antitubercular, antiviral, larvicidal and herbicidal activities.
Objective: In the present investigation, it was envisaged to synthesize a series of novel ethyl-7-substituted-3-(4-substituted benzoyl)-2-substituted indolizine-l-carboxylates by employing chromium(IV)oxide as dehydrogenating agent with triethylamine combination.
Method: Synthesis of a series of proposed polysubstituted indolizines by employing chromium(IV)oxide as dehydrogenating agent with triethylamine combination. Final compounds were characterized by spectroscopic techniques viz fourier-transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, liquid chromatography-mass spectrometry, elemental analysis and selected title compound diethyl-3-(4-cyanobenzoyl)indolizine-1,2-dicarboxylate by single crystal X-ray method.
Results: Aromatic cycloimmoniumylides undergo smooth cyclization with electron-deficient alkenes in the presence of triethylamine and DMF at room temperature to afford intermediates ethyl 7-substituted-2-substituted-3-(4-substituted benzoyl)-1,2,3,8a-tetrahydroindolizine-1-carboxylates, which on dehydrogenation with chromium(IV)oxide to obtain the title compounds ethyl-7-substituted-3-(4-substituted benzoyl)-2substituted indolizine-1 -carboxylates.
Conclusion: The research was focused on developing an efficient protocol for the synthesis of a novel series of ethyl 3-substituted benzoyl-7-substituted-2-substituted indolizine-l-carboxylates with suitable pharmacological properties in good to excellent yields.