Download PDF
Synthesis 2022; 54(18): 3989-3998
DOI: 10.1055/a-1824-6352
paper

A Direct Method for Synthesis of Fluorinated Quinazolinones and Quinoxalines Using Fluorinated Acids without Metals or Additives

Shichen Li
,
Xueyan Lv
,
Jianing Ren
,
Lei Feng
,
Chen Ma  ∗
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.
› Further Information
    Permissions and Reprints All articles of this category


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-only

Supporting 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

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • 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
    CrossrefPubMed
  • 4 Miró J, del Pozo C. Chem. Rev. 2016; 116: 11924
    CrossrefPubMed
  • 5 Ni C, Hu M, Hu J. Chem. Rev. 2015; 115: 765
    CrossrefPubMed
  • 6 Jeschke P. ChemBioChem 2004; 5: 570
    CrossrefPubMed
  • 7 Zhu Y, Han J, Wang J, Shibata N, Sodeoka M, Soloshonok VA, Coelho JA. S, Toste FD. Chem. Rev. 2018; 118: 3887
    CrossrefPubMed
  • 8 Han J, Remete AM, Dobson LS, Kiss L, Izawa K, Moriwaki H, Soloshonok VA, O’Hagan D. J. Fluorine Chem. 2020; 239: 109639
    Crossref
  • 9 Mei H, Remete AM, Zou Y, Moriwaki H, Fustero S, Kiss L, Soloshonok VA, Han J. Chin. Chem. Lett. 2020; 31: 2401
    Crossref
  • 10 Jeschke P. Pest Manag. Sci. 2017; 73: 1053
    CrossrefPubMed
  • 11 Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
    CrossrefPubMed
  • 12 Wong DT, Bymaster FP, Engleman EA. Life Sci. 1995; 57: 411
    CrossrefPubMed
  • 13 Scott LJ. Drugs 2018; 78: 1913
    CrossrefPubMed
  • 14 Scott LJ. Drugs 2019; 79: 875
    CrossrefPubMed
  • 15 Adkins JC, Noble S. Drugs 1998; 56: 1055
    CrossrefPubMed
  • 16 Roman DL, Walline CC, Rodriguez GJ, Barker EL. Eur. J. Pharmacol. 2003; 479: 53
    CrossrefPubMed
  • 17 Xiao H, Zhang Z, Fang Y, Zhu L, Li C. Chem. Soc. Rev. 2021; 50: 6308
    CrossrefPubMed
  • 18 Bhaskaran RP, Babu BP. Adv. Synth. Catal. 2020; 362: 5219
    Crossref
  • 19 Pike JA, Walton JW. Chem. Commun. 2017; 53: 9858
    CrossrefPubMed
  • 20 Wang X, Truesdale L, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 3648
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 22 Zhang X.-G, Dai H.-X, Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 11948
    CrossrefPubMed
  • 23 Novák P, Lishchynskyi A, Grushin VV. Angew. Chem. Int. Ed. 2012; 51: 7767
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 25 Zhou Y, Shen G, Sui Y, Zhou H. Tetrahedron Lett. 2016; 57: 3396
    Crossref
  • 26 Ghosh P, Mondal S, Hajra A. J. Org. Chem. 2018; 83: 13618
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 30 Almeida S, Marti R, Vanoli E, Abele S, Tortoioli S. J. Org. Chem. 2018; 83: 5104
    CrossrefPubMed
  • 31 Wang L.-C, Du S, Chen Z, Wu X.-F. Org. Lett. 2020; 22: 5567
    CrossrefPubMed
  • 32 Zhu J, Xie H, Chen Z, Li S, Wu Y. Org. Biomol. Chem. 2012; 10: 516
    CrossrefPubMed
  • 33 Zhu J, Xie H, Chen Z, Li S, Wu Y. Chem. Commun. 2011; 47: 1512
    CrossrefPubMed
  • 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
    CrossrefPubMed
  • 35 Patel B, Hilton ST. Synlett 2015; 26: 79
    Crossref
  • 36 Verma AK, Jha RR, Sankar VK, Aggarwal T, Singh RP, Chandra R. Eur. J. Org. Chem. 2011; 2011: 6998
    Crossref
  • 37 Xie C, Zhang Z, Li D, Gong J, Han X, Liu X, Ma C. J. Org. Chem. 2017; 82: 3491
    CrossrefPubMed