Synthesis 2023; 55(04): 683-691
DOI: 10.1055/a-1933-3655
paper

Trifluoromethylated Amidrazone Derivatives as Key Compounds for the Synthesis of 4-Aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles

Najmeh Zeinali
,
We gratefully acknowledge financial support of a research grant from the Rafsanjan Faculty of Vail-e-Asr University.


Abstract

A novel, efficient, and solvent-free approach for the synthesis of aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles is disclosed via the nucleophilic intramolecular cyclization reaction of trifluoromethylated amidrazone and 2,2,2-trifluoroacetic anhydride. The trifluoromethylated amidrazone intermediates used in this project are synthesized from the reaction of N-aryl-2,2,2-trifluoroacetimidoyl chloride derivatives and hydrazine hydrate at ambient temperature in excellent yields.

Supporting Information



Publikationsverlauf

Eingereicht: 08. Juli 2022

Angenommen nach Revision: 30. August 2022

Accepted Manuscript online:
30. August 2022

Artikel online veröffentlicht:
06. Oktober 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Dixit D, Verma PK, Marwaha RK. J. Iran. Chem. Soc. 2021; 18: 2535
  • 2 Nural Y, Ozdemir S, Yalcin MS, Demir B, Atabey H, Seferoglu Z, Ece A. Bioorg. Med. Chem. Lett. 2022; 55: 128453
  • 3 Veloso RV, Shamim A, Lamarrey Y, Stefani HA, Sciani JM. Bioorg. Chem. 2021; 109: 104709
  • 4 Luo L, Jia JJ, Zhong Q, Zhong X, Zheng S, Wang G, He L. Eur. J. Med. Chem. 2021; 213: 113039
  • 5 Kumar S, Khokra SL, Yadav A. Future J. Pharm. Sci. 2021; 7: 1
  • 6 Karim HA, Raauf AM, Ali KF. Syst. Rev. Pharm. 2021; 12: 190
  • 7 Patil PS, Kasare SL, Haval NB, Khedkar VM, Dixit PP, Rekha EM, Haval KP. Bioorg. Med. Chem. Lett. 2020; 30: 127434
  • 8 Sallam HH, Mohammed YH. I, Al-Ostoot FH, Sridhar MA, Khanum SA. J. Mol. Struct. 2021; 1246: 131242
  • 9 Karaali N, Aydin S, Baltas N, Mentese E. J. Heterocycl. Chem. 2020; 57: 1806
  • 10 Song MX, Huang YS, Zhou QG, Deng XQ, Yao XD. Bioorg. Chem. 2021; 106: 104505
  • 11 Mohamed MA, Abd Allah OA, Bekhit AA, Kadry AM, El-Saghier AM. J. Heterocycl. Chem. 2020; 57: 2365
  • 12 Singh K, Pal R, Khan SA, Kumar B, Akhtar MJ. J. Mol. Struct. 2021; 1237: 130369
  • 13 Alasalvar C, Oztürk N, Gokce H, Guder A, Mentese E, Bektas H. J. Biomol. Struct. Dyn. 2021; 1
  • 14 Deo PS, Rawat R, Shakya B. J. Nepal Chem. Soc. 2021; 42: 6
  • 15 Zhang J, Tang J, Chen Z, Wu XF. Adv. Synth. Catal. 2021; 363: 3060
  • 16 Kharb R, Sharma PC, Yar MS. J. Enzyme Inhib. Med. Chem. 2011; 26: 1
  • 17 Aggarwal R, Sumran G. Eur. J. Med. Chem. 2020; 205: 112652
  • 18 Wu WN, Jiang YM, Fei Q, Du HT, Yang MF. J. Heterocycl. Chem. 2020; 57: 1379
  • 19 Yang H, Xu TH, Lu SN, Chen Z, Wu XF. Org. Chem. Front. 2021; 8: 3440
  • 20 Lu SN, Yang H, Zhang J, Chen Z, Wu XF. Adv. Synth. Catal. 2021; 363: 4982
  • 21 Ismail FM. J. Fluorine Chem. 2002; 118: 27
  • 22 Klix MB, Verreet JA, Beyer M. Crop Prot. 2007; 26: 683
  • 23 Michel D, Schlosser M. Tetrahedron 2000; 56: 4253
  • 24 Welch JT. Tetrahedron 1987; 43: 3123
  • 25 Chen M, Wang XF, Wang SS, Feng YX, Chen F, Yang CL. J. Fluorine Chem. 2012; 135: 323
  • 26 Kumar BN. P, Mohana KN, Mallesha L. J. Fluorine Chem. 2013; 156: 15
  • 27 Haber J. Cas. Lek. Ces. 2001; 140: 596
  • 28 Faidallah HM, Khan KA, Asiri AM. J. Fluorine Chem. 2011; 132: 870
  • 29 Jiao S, Li Y, Gao Z, Chen R, Wang Y, Zou Z. New J. Chem. 2019; 43: 18823
  • 30 Du S, Wang LC, Yang Z, Chen Z, Wu XF. Adv. Synth. Catal. 2020; 362: 5130
  • 31 Hu S, Yang Z, Chen Z, Wu XF. Adv. Synth. Catal. 2019; 361: 4949
  • 32 Zhang J, Tang J, Chen Z, Wu XF. Chin. J. Chem. 2021; 39: 3443
  • 33 Zhang J, Xu TH, Chen Z, Wu XF. Org. Chem. Front. 2021; 8: 4490
    • 34a Barlow MG, Bell D, O’Reilly NJ, Tipping AE. J. Fluorine Chem. 1983; 23: 293
    • 34b Bell D, Eltoum AO. A, O’Reilly NJ, Tipping AE. J. Fluorine Chem. 1993; 64: 151
    • 34c Abdul-Ghani MM, Tipping AE. J. Fluorine Chem. 1995; 72: 95
  • 35 Darehkordi A, Khabazzadeh H, Saidi K. J. Fluorine Chem. 2005; 126: 1140
  • 36 Tamura K, Mizukami H, Maeda K, Watanabe H, Uneyama K. J. Org. Chem. 1993; 58: 32
  • 37 Darehkordi A, Ramezani M. Mol. Divers. 2017; 21: 305
  • 38 Reitz DB, Finkes MJ. J. Heterocycl. Chem. 1989; 26: 225