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Synthesis 2022; 54(18): 3989-3998
DOI: 10.1055/a-1824-6352
DOI: 10.1055/a-1824-6352
paper
A Direct Method for Synthesis of Fluorinated Quinazolinones and Quinoxalines Using Fluorinated Acids without Metals or Additives
We are grateful to the National Science Foundation of China (Grant No. 21572117) and the Shandong Key Research and Program (Grant No. 2019JZZY021015 and 2019GHY112053) for their financial support.
Abstract
The trifluoromethyl group only exists in synthetic compounds. Owing to the unique bioactivities of this group, the trifluoromethylation of alkanes, arenes, unsaturated compounds like olefins, aldehydes, and ketones, and heterocycles has been studied constantly in recent decades. Herein, a direct method using trifluoroacetic acid as a CF3 source for the synthesis of 2-(trifluoromethyl)quinazolin-4-ones and 4-(trifluoromethyl)pyrrolo/indolo[1,2-a]quinoxalines without any catalysts or additives is reported; a wide range of fluorinated compounds were obtained in 52%–94% yield.
Key words
fluorination - trifluoromethyl - quinazolinones - quinoxalines - metal-free - solvent-onlySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1824-6352.
- Supporting Information
Publication History
Received: 14 February 2022
Accepted after revision: 13 April 2022
Accepted Manuscript online:
13 April 2022
Article published online:
07 June 2022
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References
- 1 Dumas J, Péligot E. Ann. Pharm. 1835; 15: 246
- 2 Dumas J, Péligot E. Ann. Chim. Phys. 1836; 61: 193
- 3 Han J, Kiss L, Mei H, Remete AM, Ponikvar-Svet M, Sedgwick DM, Roman R, Fustero S, Moriwaki H, Soloshonok VA. Chem. Rev. 2021; 121: 4678
- 4 Miró J, del Pozo C. Chem. Rev. 2016; 116: 11924
- 5 Ni C, Hu M, Hu J. Chem. Rev. 2015; 115: 765
- 6 Jeschke P. ChemBioChem 2004; 5: 570
- 7 Zhu Y, Han J, Wang J, Shibata N, Sodeoka M, Soloshonok VA, Coelho JA. S, Toste FD. Chem. Rev. 2018; 118: 3887
- 8 Han J, Remete AM, Dobson LS, Kiss L, Izawa K, Moriwaki H, Soloshonok VA, O’Hagan D. J. Fluorine Chem. 2020; 239: 109639
- 9 Mei H, Remete AM, Zou Y, Moriwaki H, Fustero S, Kiss L, Soloshonok VA, Han J. Chin. Chem. Lett. 2020; 31: 2401
- 10 Jeschke P. Pest Manag. Sci. 2017; 73: 1053
- 11 Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 12 Wong DT, Bymaster FP, Engleman EA. Life Sci. 1995; 57: 411
- 13 Scott LJ. Drugs 2018; 78: 1913
- 14 Scott LJ. Drugs 2019; 79: 875
- 15 Adkins JC, Noble S. Drugs 1998; 56: 1055
- 16 Roman DL, Walline CC, Rodriguez GJ, Barker EL. Eur. J. Pharmacol. 2003; 479: 53
- 17 Xiao H, Zhang Z, Fang Y, Zhu L, Li C. Chem. Soc. Rev. 2021; 50: 6308
- 18 Bhaskaran RP, Babu BP. Adv. Synth. Catal. 2020; 362: 5219
- 19 Pike JA, Walton JW. Chem. Commun. 2017; 53: 9858
- 20 Wang X, Truesdale L, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 3648
- 21 Zhang C.-P, Wang Z.-L, Chen Q.-Y, Zhang C.-T, Gu Y.-C, Xiao J.-C. Angew. Chem. Int. Ed. 2011; 50: 1896
- 22 Zhang X.-G, Dai H.-X, Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 11948
- 23 Novák P, Lishchynskyi A, Grushin VV. Angew. Chem. Int. Ed. 2012; 51: 7767
- 24 Zhang L.-S, Chen K, Chen G, Li B.-J, Luo S, Guo Q.-Y, Wei J.-B, Shi Z.-J. Org. Lett. 2013; 15: 10
- 25 Zhou Y, Shen G, Sui Y, Zhou H. Tetrahedron Lett. 2016; 57: 3396
- 26 Ghosh P, Mondal S, Hajra A. J. Org. Chem. 2018; 83: 13618
- 27 Yang X, Sun R, Li S, Zheng X, Yuan M, Xu B, Jiang W, Chen H, Fu H, Li R. Org. Lett. 2020; 22: 7108
- 28 Natte K, Jagadeesh RV, He L, Rabeah J, Chen J, Taeschler C, Ellinger S, Zaragoza F, Neumann H, Brückner A, Beller M. Angew. Chem. Int. Ed. 2016; 55: 2782
- 29 Beck HP, Kohn T, Rubenstein S, Hedberg C, Schwandner R, Hasslinger K, Dai K, Li C, Liang L, Wesche H, Frank B, An S, Wickramasinghe D, Jaen J, Medina J, Hungate R, Shen W. Bioorg. Med. Chem. Lett. 2008; 18: 1037
- 30 Almeida S, Marti R, Vanoli E, Abele S, Tortoioli S. J. Org. Chem. 2018; 83: 5104
- 31 Wang L.-C, Du S, Chen Z, Wu X.-F. Org. Lett. 2020; 22: 5567
- 32 Zhu J, Xie H, Chen Z, Li S, Wu Y. Org. Biomol. Chem. 2012; 10: 516
- 33 Zhu J, Xie H, Chen Z, Li S, Wu Y. Chem. Commun. 2011; 47: 1512
- 34 Primas N, Suzanne P, Verhaeghe P, Hutter S, Kieffer C, Laget M, Cohen A, Broggi J, Lancelot J.-C, Lesnard A, Dallemagne P, Rathelot P, Rault S, Vanelle P, Azas N. Eur. J. Med. Chem. 2014; 83: 26
- 35 Patel B, Hilton ST. Synlett 2015; 26: 79
- 36 Verma AK, Jha RR, Sankar VK, Aggarwal T, Singh RP, Chandra R. Eur. J. Org. Chem. 2011; 2011: 6998
- 37 Xie C, Zhang Z, Li D, Gong J, Han X, Liu X, Ma C. J. Org. Chem. 2017; 82: 3491