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Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides

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Chemistry of Heterocyclic Compounds Aims and scope

2-(1,2,3-Thiadiazol-5-yl)enamines and 3-(1,2,3-triazol-4-yl)enaminones react with arylhydroxamoyl chlorides at room temperature with the exclusive formation of 3-aryl-4-(1,2,3-thiadiazol-5-yl)- and [4-(1,2,3-triazol-4-yl)carbonyl]isoxazoles in high yields. The proposed mechanism includes in situ generation of nitrile oxides, which participate in the (3+2)-dipolar cycloaddition reactions leading to the formation of the isoxazole ring.

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Notes

  1. Successively added methylamine hydrochloride (2.7 g, 40 mmol) and NaOH (1.2 g, 30 mmol) can be used as methylamine (2) source.

  2. The assignment was done on the basis of the data of a 2D HMBC experiment.

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This work was supported financially by the Russian Foundation for Basic Research (grant 14-03-01033) and the Ministry of Education and Science of the Russian Federation (State assignment 4.1626.2014/K).

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Authors and Affiliations

  1. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Ilya V. Efimov, Yuri M. Shafran, Natalia N. Volkova, Nikolai A. Beliaev, Pavel A. Slepukhin & Vasiliy A. Bakulev

  2. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi St., Yekaterinburg, 620137, Russia

    Pavel A. Slepukhin

Authors
  1. Ilya V. Efimov
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  2. Yuri M. Shafran
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  3. Natalia N. Volkova
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  4. Nikolai A. Beliaev
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  5. Pavel A. Slepukhin
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  6. Vasiliy A. Bakulev
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Correspondence to Vasiliy A. Bakulev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(9), 743–749

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Efimov, I.V., Shafran, Y.M., Volkova, N.N. et al. Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides. Chem Heterocycl Comp 52, 743–749 (2016). https://doi.org/10.1007/s10593-016-1958-8

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