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Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies

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Abstract

Simple and efficient strategies towards the synthesis of substituted spiro-oxindole and oxazolidine systems by one-pot multi-component catalyst-free reactions utilising aryl aldehydes and α-amino acids have been developed. Owing to their complicated structure and ring strain spiro-oxindole moieties are not easily synthesised. In either route 1,3-dipolar cycloadditions involving non-stabilised azomethine ylides as intermediates, generated in situ from amino acids and aldehydes, with the dipolarophile present in the reaction mixture viz. (E)-β-nitrostyrene, were utilised. The route to substituted oxazolidines involved cycloaddition to the C=O bond of a second molecule of the aldehyde.

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Acknowledgments

The authors thank the University of Calcutta for providing laboratory and spectroscopic facilities. B. Gayen thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, India. for the award of Senior Research Fellowship. B. Gayen also thanks to Dr. K. P. Dhara.

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Authors and Affiliations

  1. Department of Chemistry, Centre of Advanced Studies on Natural Products Including Organic Synthesis, University College of Science and Technology, University of Calcutta, 92, Acharya Prafulla Chandra Road, Kolkata, 700 009, India

    Biswajit Gayen & Avijit Banerji

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  1. Biswajit Gayen
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  2. Avijit Banerji
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Correspondence to Avijit Banerji.

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Gayen, B., Banerji, A. Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies. Monatsh Chem 145, 1953–1965 (2014). https://doi.org/10.1007/s00706-014-1269-7

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