Cu/TEMPO catalyzed dehydrogenative 1,3-dipolar cycloaddition in the synthesis of spirooxindoles as potential antidiabetic agents |
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Authors: | Chitrala Teja Spoorthy N Babu Ayesha Noor J Arul Daniel S Asha Devi Fazlur Rahman Nawaz Khan |
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Institution: | Organic and Medicinal Chemistry Research Laboratory, Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore-632014 Tamil Nadu India, +91-944-423-4609 ; Centre for Bio Separation Technology, Vellore Institute of Technology, Vellore-632014 India ; Department of Biomedical Sciences, School of Bioscience and Technology, Vellore Institute of Technology, Vellore-632014 India |
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Abstract: | A series of spiro-indoline-3,3′-pyrrolizin/pyrrolidin]-2-ones, 4, 5 and 6 were synthesized in a sequential manner from Cu–TEMPO catalyzed dehydrogenation of alkylated ketones, 1 followed by 1,3-dipolar cycloaddition of azomethine ylides via decarboxylative condensation of isatin, 2 and l-proline/sarcosine, 3 in high regioselectivities and yields. The detailed mechanistic studies were performed to identify the reaction intermediates, which revealed that the reaction proceeds via dehydrogenative cycloaddition. Additionally, the regio and stereochemistry of the synthesized derivatives were affirmed by 2D NMR spectroscopic studies. The synthesized derivatives were explored further with molecular docking, in vitro antioxidant, and anti-diabetic activities.A series of spiro-indoline-3,3′-pyrrolizin/pyrrolidin]-2-ones were synthesized from Cu–TEMPO catalyzed dehydrogenation followed by 1,3-dipolar cycloaddition of azomethine ylides via decarboxylative condensation, resulting in high regioselectivities and yields. |
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