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Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Research on Chemical Intermediates volume 41, pages 7847–7882 (2015)Cite this article

Abstract

A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

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Acknowledgment

The authors are grateful to the Damghan University.

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Authors and Affiliations

  1. School of Chemistry, Damghan University, 36715-364, Damghan, Iran

    Hamzeh Kiyani & Fatemeh Ghorbani

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  1. Hamzeh Kiyani
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  2. Fatemeh Ghorbani
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Correspondence to Hamzeh Kiyani.

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Kiyani, H., Ghorbani, F. Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water. Res Chem Intermed 41, 7847–7882 (2015). https://doi.org/10.1007/s11164-014-1863-7

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  • DOI: https://doi.org/10.1007/s11164-014-1863-7

Keywords

  • Three-component reaction
  • 4H-Chromenes
  • 4H-Pyrans
  • Isoxazol-5(4H)-ones
  • Potassium hydrogen phthalate
  • Cyano compounds