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Regio- and stereoselective synthesis of novel trispiropyrrolidine/thiapyrrolizidines using deep eutectic solvent as an efficient reaction media

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Abstract

An efficient synthesis of novel trispiropyrrolidine/thiapyrrolizidines has been reported by the 1,3-dipolar cycloaddition reaction of azomethine ylides with a novel dipolarophile 8,10-bis[(E)arylidene]-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-one using deep eutectic solvent (DES). The DES is cheaper, biodegradable, non-toxic, recyclable and serves as dual role of catalyst as well as solvent. The suitable azomethine ylides were generated ‘in situ’ from the reaction of substituted isatin/acenaphthenequinone and sarcosine/1,3-thiazolane-4-carboxylic acid. In this protocol generation of one new five-membered pyrrolidine ring with three contiguous stereocenters occurred in a single operation. The stereochemistry of the synthesized compounds including regio- and diastereo was confirmed by spectroscopic techniques and single-crystal X-ray of one representative compound.

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Fig. 1
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Acknowledgements

R. S thanks DST, New Delhi for start-up grant (YSS/2015/000972). We are thankful to the Central Drug research institute (CDRI), Lucknow, and MNIT, Jaipur, for the spectral analyses and elemental analyses. We are also thankful to STIC Cochin for single-crystal X-ray analysis. Crystallographic data (excluding structure factors) for trispiroderivative 8a in this letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 996220. Copy of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223-336033 or deposit@ccdc.cam.ac.uk].

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  1. Department of Chemistry, School of Basic Sciences, Jaipur National University, Jaipur, India

    Ruby Singh & Aakash Singh

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Singh, R., Singh, A. Regio- and stereoselective synthesis of novel trispiropyrrolidine/thiapyrrolizidines using deep eutectic solvent as an efficient reaction media. J IRAN CHEM SOC 14, 1119–1129 (2017). https://doi.org/10.1007/s13738-017-1062-8

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