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

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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)

Abstract

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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  27. (a) The crystal structure has been deposited at the Cambridge Crystallographic Data centre CCDC number: 1004671, molecular formula: C28H23NO2S, unit cell parameters: a 9.6859(3), b 9.8620(3), c 12.9293(4), 76.6380 (10), space group P-1. Data acquisition: The Cambridge Crystallographic Data Center; deposit , ccdc.cam.ac.uk, http://www.ccdc.cam.ac.uk/deposit, (2014) (b)The crystal structure has been deposited at the Cambridge Crystallographic Data centre CCDC number: 1004647, molecular formula: C2721NOS, unit cell parameters: a 13.0132(6), b 9.8726(5), c 17.8545(8), 108.882(2), space group P2(1)/c. Data acquisition: The Cambridge Crystallographic Data Center; deposit , ccdc.cam.ac.uk, http: // www.ccdc.cam.ac.uk / deposit, (2014)
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