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Synthesis 2022; 54(02): 429-438
DOI: 10.1055/a-1625-9538
paper

A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation

Wei Zhou‡
a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
,
Lan Yao‡
b   Inspection Department, Shanghai Blood Center, Shanghai 200051, P. R. of China
,
Yongxiurong Liu
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Lichun Shen
d   Qianweichang College, Shanghai University, Shanghai, 200444, P. R. of China
,
Jie Chen
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Hongmei Deng
e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Min Shao
e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Hui Zhang∗
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Xiaojun Tang∗
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Weiguo Cao∗
a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
f   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› InstitutsangabenThe authors are grateful to the National Natural Science Foundation of China (Grant No. 21672138) for financial support.
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Abstract

A novel synthesis of fused perfluoroalkylated 2,3-dihydroisoxazoles is achieved via oxa-Michael-aldol annulation between perfluoroalk-2-ynoates and N-hydroxyimides. This method provides a convenient route for the synthesis of pyrrolidin-2-one-fused perfluoroalkylated 2,3-dihydroisoxazoles in yields of up to 97%. Diverse and pharmaceutically attractive polycyclic scaffolds can be obtained rapidly and efficiently under these mild, catalyst-free conditions.

Key words

dihydroisoxazoles - piperidin-2-ones - perfluoroalkylated - oxa-Michael-aldol annulation - catalyst-free conditions

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1625-9538.
  • Supporting Information


Publikationsverlauf

Eingereicht: 03. August 2021

Angenommen nach Revision: 31. August 2021

Accepted Manuscript online:
31. August 2021

Artikel online veröffentlicht:
17. September 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Habeeb AG, Praveen PN, Knaus EE. J. Med. Chem. 2001; 44: 2921
      CrossrefPubMed
    • 1b Fraley ME, Garbaccio RM, Hartman GD. WO Patent WO2006023440, 2006
      PubMed
    • 2a Sailu B, Srinivas M, Satya SA, Balram B, Ram B, Taara B, Vasudha B. Pharm. Chem. 2012; 4: 2036
    • 2b Kadnor V, Pandhare G, Gadhave A, Uphade B. Rasayan J. Chem. 2011; 4: 437
    • 2c Gutierrez M, Matus MF, Poblete T, Amigo J, Vallejos G, Astudillo L. J. Pharm. Pharmacol. 2013; 65: 1796
      CrossrefPubMed
    • 2d Banerjee M, Azam AM, Sahu SK. J. Chem. Pharm. Sci. 2009; 2: 35
    • 3a Chukanov NV, Reznikov VA. Russ. Chem. Bull. 2011; 60: 379
      Crossref
    • 3b Pinho e Melo TM. V. D. Eur. J. Org. Chem. 2010; 3363
      Crossref
    • 3c Freeman JP. Chem. Rev. 1983; 83: 241
      Crossref
    • 3d Alibes R, Blanco P, Casas E, Closa M, March P, Figueredo M, Font J, Sanfeliu E, Larena AA. J. Org. Chem. 2005; 70: 3157
      CrossrefPubMed
    • 4a Giurgea C, Salama M. Prog. Neuro-Psychopharmacol. 1977; 1: 235
      Crossref
    • 4b Winblad B. CNS Drug Rev. 2005; 11: 169
      CrossrefPubMed
    • 4c Waegemans T, Wilsher CR, Danniau A, Ferris SH, Kurz A, Winblad B. Dement. Geriatr. Cogn. Disord. 2002; 13: 217
      CrossrefPubMed
    • 4d Malykh AG, Sadaie MR. Drugs 2010; 70: 287
      CrossrefPubMed
    • 4e Wheble PC. R, Sena ES, Macleod MR. Cerebrovasc. Dis. 2008; 25: 5
      CrossrefPubMed
    • 4f Gualtieri F, Manetti D, Romanelli MN, Ghelardini C. Curr. Pharm. Des. 2002; 8: 125
      CrossrefPubMed
    • 4g Mohan G, Madhwi O, Divya Y, Swati P, Rakesh Y. ACS Chem. Neurosci. 2020; 11: 2849
      CrossrefPubMed
    • 4h Aida J, Fushimi M, Kusumoto T, Sugiyama H, Arimura N, Ikeda S, Sasaki M, Sogabe S, Aoyama K, Koike T. J. Med. Chem. 2018; 61: 9205
      CrossrefPubMed
    • 5a Speck K, Magauer T. Beilstein J. Org. Chem. 2013; 9: 2048
      CrossrefPubMed
    • 5b Sanchez C, Mendez C, Salas JA. Nat. Prod. Rep. 2006; 23: 1007
      CrossrefPubMed
    • 5c Gundugdu O, Noma SA. A, Taskin T, Ates B, Kishali N. J. Mol. Struct. 2020; 1204: 127523
      Crossref
    • 5d Mikolasch A, Hessel S, Salazar MG, Neumann H, Manda K, Gordes D, Schmidt E, Thurow K, Hammer E, Lindequist U, Beller M, Schauer F. Chem. Pharm. Bull. 2008; 56: 781
      CrossrefPubMed
    • 5e Hardcastle IR, Ahmed SU, Atkins H, Farnie G, Golding BT, Griffin RJ, Guyenne S, Hutton C, Kallblad P, Kemp SJ, Kitching MS, Newell DR, Norbedo S, Northen JS, Reid RJ, Sarvanan K, Willems HM. G, Lunec J. J. Med. Chem. 2006; 49: 6209
      CrossrefPubMed
    • 5f Schneider MJ. Pyridine and Piperidine Alkaloids: An Update. In Alkaloids: Chemical and Biochemical Perspectives, Vol. 10. Pelletier SW. Elsevier Science Ltd; Oxford: 1996
      Google Scholar
    • 6a Brown ED, Wright GD. Nature 2016; 529: 336
      CrossrefPubMed
    • 6b Wright GD. Nat. Prod. Rep. 2017; 34: 694
      CrossrefPubMed
    • 6c Neto LR, Filho JT, Neves BJ, Maidana RL, Guimaraes AC, Furnham N, Andrade CH, Silva FP. Front. Chem. 2020; 8: 93
      CrossrefPubMed
    • 6d Radhika T, Babu VH. Asian J. Pharm. Clin. Res. 2019; 12: 245
      Crossref
    • 6e Alfawaz AA. S, Yassine R, Obaid A, Sandhya B, Fareeda A, Quamrul HM. Chem. Biol. Drug Des. 2020; 96: 1418
      CrossrefPubMed
    • 7a Youseftabar-Miri L, Ramazani A, Ahmadi E, Sedrpoushan A. Phosphorus, Sulfur Silicon Relat. Elem. 2007; 182: 2523
      Crossref
    • 7b Zhou Q, Chu X, Ge F, Wang Y, Lu T. Adv. Synth. Catal. 2013; 355: 2787
      Crossref
    • 7c Zhao S, Zhu Y, Wu Y, Lu T, Zhou Q. ChemistrySelect 2017; 2: 1700
      Crossref
    • 7d Xie J, Yu B, Guo C, He L. Green Chem. 2015; 17: 4061
      Crossref
    • 7e Xie J, He L, Fu H, Wang N, Wang M. Curr. Catal. 2018; 7: 60
      Crossref
    • 8a Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
      CrossrefPubMed
    • 8b Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Acena JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422
      CrossrefPubMed
    • 8c Park BK, Kitteringham NR, O’Neill PM. Annu. Rev. Pharmacol. 2001; 41: 443
      CrossrefPubMed
    • 8d Tamejiro H, Yamamoto H. Organofluorine Compounds: Chemistry and Applications . Springer-Verlag; Berlin: 2000
      Google Scholar
  • 9 For a recent review, see: Sun X, Han J, Chen J, Zhang H, Cao W. Chem. Rec. 2016; 16: 907
    CrossrefPubMed
  • 10 CCDC 1919617 (3r′) contains the supplementary crystallographic data for this paper. Unit cell parameters (3r′): space group = P2(1)/c, a = 8.504(10) Å, b = 11.766(14) Å, c = 16.165(19) Å, α = 90°, β = 90.479(14)°, γ = 90°. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
  • 11 Hamper BC. Org. Synth. 1992; 70: 246
    Crossref
  • 12 Kushch O, Hordieieva I, Novikova K, Litvinov Y, Kompanets M, Shendrik A, Opeida I. J. Org. Chem. 2020; 85: 7112
    CrossrefPubMed