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A Facile Regioselective 1,3-dipolar Cycloaddition Protocol for the Synthesis of Thiophene containing Spiro Heterocycles

Author Affiliations

  • 1Department of Chemistry, Karpagam University, Coimbatore-641 021, Tamil Nadu, INDIA

Res.J.chem.sci., Volume 4, Issue (11), Pages 23-31, November,18 (2014)


An efficient three component synthesis of novel spiropyrrolidine compounds were obtained in good-to-excellent yields from the chemo-regio-and stereoselective reaction between -unsaturated ketones with thiophene substituents and non-stabilized azomethineylides, generated in situ from acenaphthenequinone and sarcosine. This protocol has the advantages of highly efficiency, mild reaction conditions, a one-pot procedure, easy workup, short reaction times, convenient operation, and catalyst-free conditions. The synthesized compounds have been characterized by their IR, H-NMR and 13C-NMR spectral data. Single crystal analysis of compounds 5a and 5c and 2D-NMR analysis of compound 5c confirmed the structures of spiropyrrolidine derivatives.


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