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An improved protocol for the synthesis of 3,4-disubstituted isoxazol-5(4H)-ones through L-valine-mediated domino three-component strategy

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Abstract

An expeditious, metal-free protocol has been demonstrated for the synthesis of isoxazolone derivatives using domino multi-component strategy. The envisaged methodology involves the L-valine promoted three-component cyclo-condensation reaction of alkylacetoacetates, hydroxylamine hydrochloride and aldehydes in ethanol under reflux. The reaction proceeded to deliver the desired products in good to excellent yields (74–97%), exhibited good functional group tolerance and completed in less than 4 min with most of the substrates. High yields, short reaction time, noncorrosive organocatalyst, mild reaction conditions, clean reaction profiles and the absence of any tedious workup or purification are the beneficial features of this process. Moreover, quantum computational study has been performed at B3LYP/6-311G++(d, p) level to investigate the various DFT based molecular descriptors, HOMO–LUMO energy gap and electrostatic potential surface properties of the synthesized product.

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An improved protocol for the synthesis of 3,4-disubstituted isoxazol-5(4H)-ones through L-valine-mediated domino three-component strategy

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Acknowledgements

The author thanks SMVDU for providing facilities. P.K. thanks the University Grants Commission for a BSR fellowship. The contribution of IIM Jammu, Saif Chandigarh and the Department of Chemistry at University of Jammu for providing spectral data is also acknowledged.

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Authors and Affiliations

  1. Synthetic Organic Chemistry Laboratory, Faculty of Sciences, Shri Mata Vaishno Devi University, Katra, 182 320, Jammu and Kashmir, India

    Parteek Kour & Anil Kumar

  2. School of Chemical Sciences, Devi Ahilya University, Indore, 452 001, Madhya Pradesh, India

    Monika Ahuja, Pratibha Sharma & Ashok Kumar

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  1. Parteek Kour
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Correspondence to Anil Kumar.

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Kour, P., Ahuja, M., Sharma, P. et al. An improved protocol for the synthesis of 3,4-disubstituted isoxazol-5(4H)-ones through L-valine-mediated domino three-component strategy. J Chem Sci 132, 108 (2020). https://doi.org/10.1007/s12039-020-01801-5

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