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Development of Environmentally Benign Methods Towards the Synthesis of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth[1,2-e][1,3]oxazines Using Brønsted Acidic Catalysts

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Abstract

This report has described three environmentally acceptable Brønsted acidic catalytic systems (p-toluene sulfonic acid, sulfamic acid and 1,3-disulfoimidazolium trifluoroacetate [DSIM][CF3COO] ionic liquid) for the preparation of complex library of anti-diastereomer of 2,3-dihydro-1,2,3-trisubstituted-1H-naphth [1,2-e][1,3]oxazines 4 from the three components reaction of 2-naphthol, p-substituted aromatic aldehydes and primary amines in 25 % aqueous ethanol at room temperature or in neat conditions at 80 °C. The reactions utilized 15 mol% of the two conventional acids to produce 82–97 % of naphthoxazines during 10–30 min. The same reactions could also be performed satisfactorily within 8–20 min employing 10 mol% of task specific acidic 1,3-disulfoimidazolium trifluoroacetate [DSIM][CF3COO] as catalyst. The three catalysts were recycled for four runs in aqueous ethanol with excellent catalytic activity.

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Acknowledgments

The authors are thankful to Sophisticated Analytical Instrumentation Centre, Tezpur University, for analysis of various samples for this work and also to CSIR, New Delhi, India for granting a research project no. 02(0067)/12/EMR-II to the corresponding author.

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Authors and Affiliations

  1. Department of Chemical Sciences, Tezpur University, Napaam, Tezpur, Assam, 784028, India

    Arup Kumar Dutta, Pinky Gogoi, Manas Pratim Saikia & Ruli Borah

Authors
  1. Arup Kumar Dutta
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  2. Pinky Gogoi
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  3. Manas Pratim Saikia
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  4. Ruli Borah
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Corresponding author

Correspondence to Ruli Borah.

Electronic supplementary material

Below is the link to the electronic supplementary material.

10562_2015_1678_MOESM1_ESM.doc

This document includes the spectra of new product 4 and melting point of other known trisubstituted naphthoxazine derivatives. Supplementary material 1 (DOC 7899 kb)

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Dutta, A.K., Gogoi, P., Saikia, M.P. et al. Development of Environmentally Benign Methods Towards the Synthesis of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth[1,2-e][1,3]oxazines Using Brønsted Acidic Catalysts. Catal Lett 146, 902–908 (2016). https://doi.org/10.1007/s10562-015-1678-1

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  • DOI: https://doi.org/10.1007/s10562-015-1678-1

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