A Simple and Efficient Approach for the Synthesis of Aryl-3-(trifluoromethyl)-1H-1,2,4-triazol-5(4H)-one Derivatives

Abstract

In this work, a series of 4-aryl-3-(trifluoromethyl)-1H-1,2,4-triazol-5(4H)-one derivatives is synthesized through nucleophilic intramolecular cyclization reactions of ethyl 2-(2,2,2-trifluoro-1-(arylimino)ethyl)hydrazine-1-carboxylate intermediates, which are themselves prepared in high yields via reactions of ethyl chloroformate and N-aryl-2,2,2-trifluoroacetimidoyl chloride derivatives. Some of the merits of the reported procedure are an operationally simple and concise method, the ready availability of starting materials, excellent product yields, no formation of harmful by-products and easy purification of the products.

Key words

4-aryl-3-(trifluoromethyl)-1H-1,2,4-triazol-5(4H)-ones - ethyl chloroformate - ethyl 2-(2,2,2-trifluoro-1-(arylimino)ethyl)hydrazine-1-carboxylates - trifluoroacetimidoyl chlorides - trifluoroacetimidohydrazides - N-heterocycles

• References

• 1 Bahceci S, Yueksek H, Ocak Z, Azakli I, Alkan M, Oezdemir M. Collect. Czech. Chem. Commun. 2002; 67: 1215
• 2 Gursoy Kol O, Yuksek H. J. Chem. 2010; 7: 123
• 3 Suleymanoglu N, Ustabaş R, Alpaslan YB, Unver Y, Turan M, Sancak K. J. Mol. Struct. 2011; 989: 101
• 4 Demirbaş N, Ugurluoglu R, Demirbaş A. Bioorg. Med. Chem. 2002; 10: 3717
• 5 Zhang X, Luo J, Li Q, Xin Q, Ye L, Zhu Q, Shi Z, Zhang F, Chu B, Liu Z, Jiang Y. Eur. J. Med. Chem. 2021; 226: 113812
• 6 Zhang Y, Zhou J, Pan W, Wu X, Wang S. Lett. Drug Des. Discovery 2010; 7: 18
• 7 Shi W, Nacev BA, Aftab BT, Head S, Rudin CM, Liu JO. J. Med. Chem. 2011; 54: 7363
• 8 Pace JR, DeBerardinis AM, Sail V, Tacheva-Grigorova SK, Chan KA, Tran R, Raccuia DS, Wechsler-Reya RJ, Hadden MK. J. Med. Chem. 2016; 59: 3635
• 9 Gitto R, Orlando V, Quartarone S, De Sarro G, De Sarro A, Russo E, Ferreri G, Chimirri A. J. Med. Chem. 2003; 46: 3758
• 10 Hu Y, Ruan W, Gao A, Zhou Y, Gao L, Xu M, Gao J, Li J, Pang T. Pharmazie 2017; 72: 707
• 11 Sabat M, Dougan DR, Knight B, Lawson JD, Scorah N, Smith CR, Taylor ER, Vu P, Wyrick C, Wang H, Balakrishna D, Hixon M, Madakamutil L, McConn D. J. Med. Chem. 2021; 64: 12893
• 12 Lv G, Zhang DL, Wang D, Pan L, Liu Y. J. Struct. Chem. 2019; 60: 1173
• 13 An F, Xuan X, Liu Z, Bian M, Shen Q, Quan Z, Zhang G, Wei C. Molecules 2022; 27: 5035
• 14 Liu S, Qian X, Song G, Chen J, Weidong C. J. Fluorine Chem. 2000; 105: 111
• 15 Liu J, Nie M, Wang Y, Hu J, Zhang F, Gao Y, Liu Y, Gong P. Eur. J. Med. Chem. 2016; 123, 431
• 16 Zhou C.-H, Wang Y. Curr. Med. Chem. 2012; 19: 239
• 17 Han S, Zhang FF, Xie X, Chen JZ. Eur. J. Med. Chem. 2014; 74: 73
• 18 Yang P, Cheng G, Tang J, Hu W, Zhang G, Yang H. Cryst. Growth Des. 2022; 23: 207
• 19 Weng JQ, Wang L, Liu XH. J. Chem. Soc. Pak. 2012; 34: 1248
• 20 Dayan FE, Green HM, Weete JD, Hancock HG. Weed Sci. 1996; 44: 797
• 21 Dayan FE, Duke SO, Weete JD, Hancock HG. Pestic. Sci. 1997; 51: 65
• 22 Pilgram KH. Synth. Commun. 1985; 15: 697
• 23 Grant SM, Clissold SP. Drugs 1989; 37: 310
• 24 Schiller DS, Fung HB. Clin. Ther. 2007; 29: 1862
• 25 Zhang C, Yan K, Fu C, Peng H, Hawker CJ, Whittaker AK. Chem. Rev. 2021; 122: 167
• 26 Haranahalli K, Honda T, Ojima I. J. Fluorine Chem. 2019; 217: 29
• 27 Caron S. Org. Process Res. Dev. 2020; 24: 470
• 28 Jaroschik F. Chem. Eur. J. 2018; 24: 14572
• 29 Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
• 30 Wei ZY, Cui BR, Cui X, Wu YL, Fu Y, Liu LP, Piao HR. Chem. Biol. Drug Des. 2017; 89: 47
• 31 You Y, Chen Y, You C, Wang J, Weng ZS. Org. Biomol. Chem. 2019; 17: 9343
• 32 Du S, Wang WF, Song Y, Chen Z, Wu XF. Org. Lett. 2021; 23: 974
• 33 Zheng Y, Wang SB, Cao X, Liu DC, Shu B, Quan ZS. Drug Res. 2014; 64: 40
• 34 Nagy D, Pilipecz MV, Kiss LA, Alekszi-Kaszas A, Simon A, Schlosser GZ, Nemes P, Varga TR. Synth. Commun. 2021; 51: 1956
• 35 Wu W, Wang J, Wang Y, Huang Y, Tan Y, Weng Z. Angew. Chem. Int. Ed. 2017; 56: 10476
• 36 Wang Z, Yuan Z, Han X, Weng Z. Adv. Synth. Catal. 2018; 360: 2178
• 37 Luo B, Weng Z. Chem. Commun. 2018; 54: 10750
• 38 Chen Y, You Y, Weng Z. Org. Chem. Front. 2019; 6: 213
• 39 Wang J, Weng Z. Eur. J. Org. Chem. 2019; 1330
• 40 Yan W, Wang R, Zhang T, Deng H, Chen J, Wu W, Weng Z. Org. Biomol. Chem. 2018; 16: 9440
• 41 Darehkordi A, Khabazzadeh H, Saidi K. J. Fluorine Chem. 2005; 126: 1140
• 42 Zeinali N, Darehkordi A. Synthesis 2023; 55: 683