Fruit juice of Citrus limon as a biodegradable and reusable catalyst for facile, eco-friendly and green synthesis of 3,4-disubstituted isoxazol-5(4H)-ones and dihydropyrano[2,3-c]-pyrazole derivatives

Abstract

Fruit juice of Citrus limon (lemon juice) has been utilized as a natural and renewable catalyst for the green and environmentally friendly preparation of 3,4-disubstituted isoxazol-5(4H)-one derivatives and 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives in hydroalcoholic media at 90 °C. A one-pot three-component reaction of β-oxoesters with hydroxylamine hydrochloride and various aromatic aldehydes afforded 3,4-disubstituted isoxazole-5(4H)-one derivatives in excellent yields. The rate constant (K = 6.12 × 10−2 min−1 at 25 °C) for the formation of isoxazole derivative (1g) was also calculated. Similarly, a four-component reaction of ethyl acetoacetate, hydrazine hydrate, aryl aldehydes, and malononitrile gives pyrano[2,3-c]-pyrazole derivatives in very good yields. After completion of the reaction, the products were isolated by simple filtration. A simple work-up process, high product yields, short reaction times, and the use of an inexpensive and biodegradable catalyst are the advanced rewards of the present protocol.

Graphical Abstract

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Acknowledgments

The authors are thankful to the Department of Chemistry, Gujarat University, Ahmedabad, for providing the necessary facilities. UGC-Info net and INFLIBNET Gujarat University are acknowledged for providing the e-resource facilities, the NFDD Centre for proton NMR and carbon NMR, and the Synzeal Research Laboratory for mass spectroscopy. R.H.V. is thankful to UGC-BSR (F.7-74/2007 (BSR)) for financial assistance.

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Correspondence to Hitesh D. Patel.

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Vekariya, R.H., Patel, K.D. & Patel, H.D. Fruit juice of Citrus limon as a biodegradable and reusable catalyst for facile, eco-friendly and green synthesis of 3,4-disubstituted isoxazol-5(4H)-ones and dihydropyrano[2,3-c]-pyrazole derivatives. Res Chem Intermed 42, 7559–7579 (2016). https://doi.org/10.1007/s11164-016-2553-4

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Keywords

  • Isoxazole-5(4H)-ones
  • Pyrano[2,3-c]-pyrazole
  • Lemon juice
  • One-pot
  • Multi-component reaction
  • Homogeneous catalysis
  • Green synthesis