Cu/TEMPO catalyzed dehydrogenative 1,3-dipolar cycloaddition in the synthesis of spirooxindoles as potential
Chitrala Teja1, Spoorthy N Babu2, Ayesha Noor2
1Organic and Medicinal Chemistry Research Laboratory, Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology Vellore-632014 Tamil Nadu India nawaz_f@yahoo.co.in +91-944-423-4609.
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.
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