A Competitive Substitution of the Difluoromethoxy Group in Aminodehalogenation Reactions of Aromatic Nitro Compounds

Authors

DOI:

https://doi.org/10.24959/ophcj.25.329747

Keywords:

difluoromethoxynitrobenzenes, difluoromethoxy group, amination, nucleophilic substitution

Abstract

The interaction of substituted nitrobenzenes containing activated halogen atoms (fluorine or chlorine) and the difluoromethoxy group with an aqueous solution of ammonia at high pressure and temperature of 80 - 160 °C was studied. It has been found that under the conditions studied, the difluoromethoxy group can be replaced by the amino group as a pseudohalogen. It has been shown that the reactivity of the difluoromethoxy group in the same positions is lower than that of the fluorine atom, but significantly higher than that of the chlorine atom.

Supporting Agency

  • The authors received no specific funding for this work.

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References

  1. Lu Y., Liu C., Chen Q-Y. Recent Advances in difluoromethylation reactions. Curr. Org. Chem. 2015, 19 (16), 1638 - 1650. http://dx.doi.org/10.2174/1385272819666150615235605.
    |
  2. Mignani, S.; Audiau, F.; Blevec, J. L.; Nemecek, C.; Barreau, M.; Jimonet, P.; Gueremy, C. Versatile Methods for the Synthesis of 2-Amino-6-Trifluoromethoxy-(Nitro)Benzothiazoles. Synthetic Communications 1992, 22 (19), 2769 - 2780. https://doi.org/10.1080/00397919208021542.
    |
  3. Wang, P.; Zheng, G.; Wang, Y.; Wang, X.; Wei, H.; Xiang, W. Highly Practical and Cost-Efficient Synthesis of Telmisartan: An Antihypertensive Drug. Tetrahedron 2012, 68 (11), 2509 - 2512. https://doi.org/10.1016/j.tet.2012.01.056.
    |
  4. Jacitho J.D., Clark R.C., Sheng T., Oballa R.N., Stock N.S., Roppe J.R. Arylcarboxamides and uses thereof. WO 2017/192304 A1, 2017.
  5. Suzuki R., Katayama K., Uedo S., Sugumoto Y., Watanabe H. Benzimidazole derivatives. WO 2020/095912 A1, 2020.
  6. Yagupol’skii, L. M.; Fialkov, Yu. A.; Tarasova, E. V. Clofelin Analogs Containing Difluoromethoxy Groups. Pharm Chem J 2006, 40 (4), 189 - 193. https://doi.org/10.1007/s11094-006-0089-4.
  7. Shen, T. Y.; Lucas, S.; Sarett, L. H. Chlorodifluoromethane as a Difluoromethylating Agent. Tetrahedron Letters 1961, 2 (2), 43 - 47. https://doi.org/10.1016/S0040-4039(01)99204-4.

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Published

2025-06-03

How to Cite

(1)
Petko, K. I.; Filatov, A. A.; Yurchenko, O. O.; Volokitin, O. V. A Competitive Substitution of the Difluoromethoxy Group in Aminodehalogenation Reactions of Aromatic Nitro Compounds. J. Org. Pharm. Chem. 2025, 23, 29-34.

Issue

Vol. 23 No. 2 (2025): Issue in Progress

Section

Original Researches

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