Tandem Reactions of Thermolysis and [3+2] Cycloaddition in the Synthesis of 3-Hetaryl-4-Nitrofuroxans from 4-Nitrofuroxannitrolic Acid

A tandem method of synthesis of 3-hetaryl-4-nitrofuroxans was developed based on the one-pot sequence of thermolysis of 4-nitrofuroxannitrolic acid to the corresponding 4-nitro-3-furoxancarbonitrile oxide and [3+2] cycloaddition of the latter to acetylenes and olefins. It was established that the synthesized 3-(isoxazol-3-yl)- and 3-(isoxazolin-3-yl)-4-nitrofuroxans are formed with high regioand diastereoselectivity.

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Correspondence to Leonid L. Fershtat.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 607–610

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Larin, A.А., Fershtat, L.L. & Makhova, N.N. Tandem Reactions of Thermolysis and [3+2] Cycloaddition in the Synthesis of 3-Hetaryl-4-Nitrofuroxans from 4-Nitrofuroxannitrolic Acid. Chem Heterocycl Comp 56, 607–610 (2020). https://doi.org/10.1007/s10593-020-02706-4

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Keywords

  • nitrofuroxans
  • nitrolic acids
  • 1,2,5-oxadiazoles
  • cycloaddition
  • regioselectivity