Efficient Synthesis of N-Phenyl-4-(trifluoromethyl)thiazol-2-amine and Its Antibacterial Activity

Xing Tian; Jin Zhang; Yang Li

doi:10.1055/a-2518-6288

Synlett, Table of Contents

Synlett 2025; 36(09): 1272-1276
DOI: 10.1055/a-2518-6288

letter

Efficient Synthesis of N-Phenyl-4-(trifluoromethyl)thiazol-2-amine and Its Antibacterial Activity

Xing Tian

^aSchool of Chemistry and Chemical Engineering, Shaanxi Normal University. 710119, Xi’an, P. R. of China

,

Jin Zhang

^bSchool of Chemistry and Chemical Engineering, Xi’an Polytechnic University. 710048, Xi’an, P. R. of China

,

Yang Li ∗

^bSchool of Chemistry and Chemical Engineering, Xi’an Polytechnic University. 710048, Xi’an, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

N-Phenyl-4-(trifluoromethyl) thiazole-2-amine is an important class of fluorinated heterocyclic compounds, particularly in the fields of fungicides and insecticides. However, there are very limited reports on the synthesis of such compounds. Here, we report a concise and efficient new method for synthesizing this thiazol-2-amine, which has good substrate versatility, strong functional group tolerance, and a single-product structure. The product structure and yield can be effectively and selectively controlled by adding or not adding alkali and other factors. Bactericidal activity tests showed that most of these compounds exhibit bactericidal activity, with the best bactericidal rate reaching 99%.

Key words

trifluoromethyl - thiazole-2-amine - phenylthiourea - transition-metal free - bactericidal activity

Full Text

References

References and Notes

1a Mikami K, Itoh Y, Yamanaka M. Chem. Rev. 2004; 104: 1
1b Kirk KL. Org. Process Res. Dev. 2008; 2: 305
1c Saito A, Kumagai N, Shibasaki M. Angew. Chem. Int. Ed. 2017; 56: 5551
1d O'Hagan D, Schaffrath C, Cobb SL, Hamilton JT. G, Murphy CD. Nature 2002; 416: 279

2a Pitterna T, Böger M, Maienfisch P. Chimia 2004; 58 (03) 108
2b Bégué J.-P, Bonnet-Delpon D. J. Fluorine Chem. 2006; 127 (08) 992
2c Hagmann WK. J. Med. Chem. 2008; 51 (15) 4359
2d Salwiczek M, Nyakatura EK, Gerling U, Ye S, Koksch B. Chem. Soc. Rev. 2012; 41: 2135
2e Foster RW, Lenz EN, Simpkins NS, Stead D. Chem. Eur. J. 2017; 23 (37) 8810

3a Welch JT. Tetrahedron 1987; 43 (14) 3123
3b Ismail FM. D. J. Fluorine Chem. 2002; 118: 27
3c Böhm HJ, Banner D, Bendels S, Kansy M, Kuhn B, Muller K, Obst-Sander U, Stahl M. ChemBioChem 2004; 5: 637
3d See ref. 2c
3e Cho EJ, Senecal TD, Kinzel T, Zhang Y, Watson DA, Buchwald SL. Science 2010; 328: 1679

4a Rodrigues I, Bonnet-Delpon D, Bégué J.-P. J. Org. Chem. 2001; 66: 2098
4b Schlosser M. Angew. Chem. Int. Ed. 2006; 45: 5432
4c Meanwell NA. J. Med. Chem. 2011; 54: 2529

5a Motoki R, Kanai M, Shibasaki M. Org. Lett. 2007; 9: 2997
5b Honey MA, Pasceri R, Lewis W, Moody CJ. J. Org. Chem. 2012; 77: 1396

6a Parise L, Pelagalli A, Pellacani L, Sciubba F, Vergari MC, Fioravanti S. J. Org. Chem. 2016; 81: 2864
6b Chen P, Yue Z.-T, Zhang J.-Y, Lv X, Wang L, Zhang J.-L. Angew. Chem. Int. Ed. 2016; 55: 13316

7a Muller K, Faeh C, Diederich F. Science 2007; 317: 1881
7b Ma JA, Cahard D. J. Fluorine Chem. 2007; 128: 975
7c Hagooly Y, Gatenyo J, Hagooly A, Rozen S. J. Org. Chem. 2009; 74: 8578

8a See ref. 7c
8b Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev. 2011; 111: 455

9a Katagiri T, Katayama Y, Taeda M, Ohshima T, Iguchi N, Uneyama K. J. Org. Chem. 2011; 76: 9305
9b Studer AA. Angew. Chem. Int. Ed. 2012; 51: 8950
9c See ref. 4b
9d Luo B.-B, Weng Z.-Q. Chem. Commun. 2018; 54: 10750

10a Morandi B, Carreira EM. Org. Lett. 2011; 13: 5984
10b Ji S.-L, Alkil AE, Su Y.-P, Xia X.-W, Chong S.-Y, Wang K.-H, Huang D.-F, Fu Y, Hu Y.-L. Synlett 2015; 26: 1725
10c Alonso C, Marigorta EM, Rubiales G, Palacios F. Chem. Rev. 2015; 115: 1847
10d Wu W, Weng Z.-Q. Synthesis 2018; 50: 1958

11a Morisaki K, Morimoto H, Ohshima T. Chem. Commun. 2017; 53: 6319
11b Mszar NW, Mikus MS, Torker S, Haeffner F, Hoveyda AH. Angew. Chem. Int. Ed. 2017; 56: 8736
11c Wang D, Carlton CG, Tayu M, McDouall JJ. W, Perry GJ. P, Procter DJ. Angew. Chem. Int. Ed. 2020; 59: 15918

12a Takahashi K, Ano Y, hatani N. Chem. Commun. 2020; 56: 11661
12b Alberca S, Matador E, Iglesias-Sigüenza J, Retamosa MC, Fernández R, Lassaletta JM, Monge D. Chem. Commun. 2021; 57: 11835

13a Zhang H.-Y, Huo W.-G, Ge C, Zhao J.-Q, Zhang Y.-C. Synlett 2017; 28: 962
13b Liu X.-D, Wang Y, Ma H.-Y, Xing C.-H, Yuan Y, Lu L. Tetrahedron 2017; 73: 2283
13c Chen F.-F, Chang Z.-X, Paidamoyo C, Zeng X.-F, Wang Y.-J, Han X.-Y. Synlett 2019; 30: 240

14a Zhang Q.-W, Hartwig JF. Chem. Commun. 2018; 54: 10124
14b Fujita T, Ide K, Jankins TC, Nojima T, Ichikawa J. Asian J. Org. Chem. 2019; 8: 637
14c Mykhailiuk PK. Chem. Rev. 2020; 120: 12718
14d Li S.-R, Yan W.-W, Shi J.-J, Dan T.-T, Han Y.-J, Cao Z.-C, Yang M.-Y. ACS Catal. 2023; 13: 2142

15a Burriss A, Edmunds AJ. F, Emery D, Hall RG, Jacob O, Schaetzer J. Pest Manage. Sci. 2018; 74: 1228
15b Liu X.-L, Liu H.-M, Bian C, Wang K.-H, Wang J.-J, Huang D.-F, Su Y.-P, Lv X.-B, Hu Y.-L. J. Org. Chem. 2022; 87: 5882
15c Khoroshilova OV, Boyarskaya IA, Vasilyev AV. J. Org. Chem. 2022; 87: 15845
15d Vayer M, Mayer RJ, Moran J, Lebœuf D. ACS Catal. 2022; 12: 10995
15e Kim H, Jung Y.-J, Cho SH. Org. Lett. 2022; 24: 2705

16a Onyeagusi CI, Malcolmson SJ. ACS Catal. 2020; 10: 12507
16b Yang T.-Y, Deng Z.-B, Wang K.-H, Li P.-F, Huang D.-F, Su Y.-P, Hu Y.-L. J. Org. Chem. 2020; 85: 924
16c Liu X, Liu L, Huang T.-Z, Zhang J.-J, Tang Z, Li C.-Y, Chen T.-Q. Org. Lett. 2021; 23: 4930
16d Zhang X.-L, Ning Y.-Q, Liu Z.-H, Li S, Zanoni G, Bi X.-H. ACS Catal. 2022; 12: 8802

17a Xu S.-X, Deng Y.-P, He J.-J, Zeng Q.-D, Liu C, Zhang Y, Zhu B, Cao S. Org. Lett. 2021; 23: 5853
17b Liu S, Huang Y.-G, Wang J, Qing F.-L, Xu X.-H. J. Am. Chem. Soc. 2022; 144: 1962

18a Liu Y, Huang J.-Q, Sun Z.-D, Deng Y.-P, Qian Y.-H, Huang Q.-C, Cao S. Org. Biomol. Chem. 2024; 22: 4641
18b Huang Z.-L, Yang H, Lai X.-B, Li J, Yang W.-R, Zheng J. J. Org. Chem. 2024; 89: 12387

19a Zhang X.-X, Liu G.-Y, Peng Y.-Y, Li H, Zhou Y.-R. Eur. J. Org. Chem. 2022; e202200658
19b Lu D, Li S.-S, Yang X.-G, Yin S.-F, Kambe N, Qiu R.-H. Org. Lett. 2022; 24: 5197
19c Zhang J.-D, Feng X.-M, Guo T.-Y, Han X.-L, Liu H.-D, Li X.-Y, Wang X, Li H.-S, Li X.-J. ChemistrySelect 2023; 8: e202301062
19d Liu H, He X, Chen Z.-C, Zhang J.-C, Fang X.-J, Sun Z.-Z, Chu W.-Y. Chem. Asian J. 2023; 18: e202300039

20a Tang Y, Yu Q, Ma S.-M. Org. Chem. Front. 2017; 4: 1762
20b Keerthika K, Nath S, Geetharani K. Catal. Sci. Technol. 2020; 10: 7142

21a Kundu BK, Han C, Srivastava P, Nagar S, White KE, Krause JA, Elles CG, Sun Y.-J. ACS Catal. 2023; 13: 8119
21b Aradi K, Kiss L. Synthesis 2023; 55: 1834

22 Lu Y, Liu Z.-R, Liu C, Wu Y.-P, Li L, Liu S.-Y, Wang H, Gao W, Liu Z.-X, Chen J.-B. Org. Chem. Front. 2023; 10: 1283
23 Zhao X, Zhong B, Dong L.-K, Zhang Y.-S, Luo H.-T, Yang J.-D, Cheng J.-P. Chem. Eur. J. 2024; 30: e202400995

24a Wang Y.-X, Li S.-J, Jiang F, Lan Y, Wang X.-M. J. Am. Chem. Soc. 2024; 146: 19286
24b Guo P, Pu G.-L, Wang G.-R, Zeng L.-Y, Li W.-P, Li X.-F, Zhou P.-P, He C.-Y. Org. Lett. 2024; 26: 3097

25 Song Q.-L, Zhang L, Wang B, Chen Z.-R, Jin W.-W, Xia Y, Wu S.-F, Liu C.-J, Zhang Y.-H. Org. Lett. 2024; 26: 3685

26a Zhao X.-W, Gao X, Zhao F.-L, Wang L, Zhang M, Zhou N.-N. Org. Lett. 2024; 26: 7261
26b Han J.-F, Gao F.-L, Chen L, He Z.-X, Lin Y.-Q, Ye K.-Y. Chem. Asian J. 2024; 13: e202300579
26c Tang L, Jia F.-J, Yu R.-J, Wei X.-M, Zhang L.-F, Lv G, Zhou Q.-J. J. Org. Chem. 2024; 89: 13117

27 Ding Y, Liu Y, Ge J, Wu X, Li Z, Cheng G. J. Org. Chem. 2024; 89: 12255
28 Emilia O, Magdalena B, Marcin KK, Grzegorz M, Heina H. J. Fluorine Chem. 2019; 220: 35
29 Tanaka K, Nomura K, Oda H, Yoshida S, Mitsuhashi K. J. Heterocycl. Chem. 1991; 28: 907
30 Wagdy RA, Abutaleb NS, Fathalla RK, Elgammal Y, Weck S, Pal R, Fisher PD, Ducho C, Abadi SH, Seleem MN, Engel M, Abdel-Halim M. Eur. J. Med. Chem. 2023; 261: 115789
31 Rajendra MA, Naseem M, Joy MN, Sunil K, Sajith AM, Howari F, Nazzal Y, Xavier C, Alshammari MB, Haridal KR. Mol. Diversity 2022; 26: 1761
32 Nguyen W, Jacobson J, Jarman KE, Jousset SH, Haety L, McMahon J, Lewin SR, Purcell DF, Sleebs BE. J. Med. Chem. 2019; 62: 5148
33 Wilkes MC, Lavrik PB, Greenplate J. J. Agric. Food Chem. 1991; 39: 1652
34 Colella M, Musci P, Carlucci C, Lillini S, Tomassetti M, Aramini A, Degennaro L, Luisi R. ACS Omega 2018; 3: 14841

35a Li Z.-B, Zhang J, Shi Y.-R, Li H, Yang M.-G, Zhu W.-Q, Fan Q.-W, Li Y. Synlett 2024; 19: 2241
35b Li Y, Shi Y.-R, Li Z.-B, Li H, Zhu W.-Q, Fan Q.-W, Li X.-Y. Synlett 2025; 2: 186

36a Li Y, Jing Y, Shi Y.-R, Li H, Yang M.-G, Kou Y.-L, Fan Q.-W. Eur. J. Org. Chem. 2024; 27: e202301255
36b Zhong M, Li X.-Y, Zhang J, Chen L, Hu Y.-L, Li Y. Asian J. Org. Chem. 2024; e202400541
36c Zhao X.-W, Zhu W.-Q, Jing Y, Shi Y.-R, Zhang J, Li H, Yang M.-G, Fan Q.-W, Li Y. Chem. Eur. J. 2024; 30: e202304056

37a Babbaud C, Kitchell AG, Labots H, Reuteb G, Simonsen B. Fleischwirtschaft 1967; 47: 1313
37b Kramer BJ. M, Gilbert RJ. J. Hyg. 1978; 81: 151

38 CCDC 2405407 (3a) and 2405408 (4a) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.

Supplementary Material

Supporting Information