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Hypervalent iodine-induced formation of 3,5-disubstituted isoxazoles via [3 + 2] cycloaddition of diynes with aldoximes

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Abstract

A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing 3,5-disubstituted isoxazoles in moderate to good yields with high regioselectivity at room temperature. This transformation was carried out in the presence of [bis(trifluoroacetoxy)iodo]benzene as a promoter and demonstrated high levels of functional-group tolerance.

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References

  1. Joule JA, Mills K (2000) Heterocyclic chemistry, 4th edn. Blackwell, Oxford

    Google Scholar 

  2. Kögel B, Christoph T, Friderichs E, Hennies HH, Matthiesen T, Schneider J, Holzgrabe U (1998) CNS Drug Rev 4:54

    Article  Google Scholar 

  3. McAteer CH, Balasubramanian M, Murugan R (2008) In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK (eds) Comprehensive heterocyclic chemistry III, vol 7. Elsevier, Oxford, p 310

    Google Scholar 

  4. Magedov IV, Manpadi M, van Slambrouck S, Steelant WFA, Rozhkova E, Przhevalskii NM, Rogelj S, Kornienko A (2007) J Med Chem 50:5183

    Article  CAS  Google Scholar 

  5. Sharma P, Gangopadhyay D, Mishra P, Mishra H, Singh R (2016) J Med Chem 59:3418

    Article  CAS  Google Scholar 

  6. Kalwat M, Huang Z, Wichaidit C, McGlynn K, Earnest S, Savoia C, Dioum E, Schneider J, Hutchison M, Cobb M (2016) ACS Chem Biol 11:1128

    Article  CAS  Google Scholar 

  7. Yoon H, Kwak Y, Choi S, Cho H, Kim ND, Sim T (2016) J Med Chem 59:358

    Article  CAS  Google Scholar 

  8. Vilela G, Fernandes T, Rosa R, Kelly S, Sitney K, Merlo A (2016) Polym Bull 73:959

    Article  CAS  Google Scholar 

  9. Refat HM, Fadda AA (2016) J Heterocycl Chem 53:1129

    Article  CAS  Google Scholar 

  10. Velaparthi S, Brunsteiner M, Uddin R, Wan B, Franzblau SG, Petukhov PA (2008) J Med Chem 51:1999

    Article  CAS  Google Scholar 

  11. Waller CC, Cawley AT, Suann CJ, Ma P, McLeod MD (2016) J Pharm Biomed Anal 124:198

    Article  CAS  Google Scholar 

  12. Rakesh KS, Jagadish S, Balaji KS, Zameer F, Swaroop TR, Mohan CD, Jayarama S, Rangappa KS (2016) Inflammation 39:269

    Article  CAS  Google Scholar 

  13. Moger M, Pradhan A, Singh A, Govindaraju DRC, Hindupur RM, Pati HN (2016) Med Chem Res 25:449

    Article  CAS  Google Scholar 

  14. Pedada SR, Yarla NS, Tambade PJ, Dhananjaya BL, Bishayee A, Arunasree KM, Philip GH, Dharmapuri G, Aliev G, Rangaiah SPG (2016) Eur J Med Chem 112:289

    Article  CAS  Google Scholar 

  15. Kumar V, Kaur K (2015) J Fluorine Chem 180:55

    Article  CAS  Google Scholar 

  16. Giustiniano M, Mercalli V, Cassese H, Maro SD, Galli U, Novellino E, Tron GC (2014) J Org Chem 79:6006

    Article  CAS  Google Scholar 

  17. Kondacs LA, Pilipecz MV, Mucsi Z, Balázs B, Gáti T, Nyerges M, Dancsó A, Nemes P (2015) Eur J Org Chem 31:6872

    Article  Google Scholar 

  18. Hu F, Zostak M (2015) Adv Synth Catal 357:2583

    Article  CAS  Google Scholar 

  19. Hashimoto T, Maruoka K (2015) Chem Rev 115:5366

    Article  CAS  Google Scholar 

  20. Yin C, Lin L, Zhang D, Feng J, Liu X, Feng X (2015) J Org Chem 80:9691

    Article  CAS  Google Scholar 

  21. Augustine JK, Akabote V, Hegde SG, Alagarsamy P (2009) J Org Chem 74:5640

    Article  CAS  Google Scholar 

  22. Grecian S, Fokin VV (2008) Angew Chem Int Ed 47:8285

    Article  CAS  Google Scholar 

  23. Kesornpun C, Aree T, Mahidol C, Ruchirawat S, Kittakoop P (2016) Angew Chem Int Ed 55:3997

    Article  CAS  Google Scholar 

  24. Jawalekar AM, Reubsaet E, Rutjes FPJ, van Delft FL (2011) Chem Commun 47:3198

    Article  CAS  Google Scholar 

  25. Yoshimura A, Middleton KR, Todora AD, Kastern BJ, Koski SR, Maskaev AV, Zhdankin VV (2013) Org Lett 15:4010

    Article  CAS  Google Scholar 

  26. Singhal A, Parumala SKR, Sharma A, Peddinti RK (2016) Tetrahedron Lett 57:719

    Article  CAS  Google Scholar 

  27. Jeyaveeran J, Praveen C, Arun Y, Prince A, Perumal PP (2016) J Chem Sci 128:73

    Article  CAS  Google Scholar 

  28. Cerniauskaite D, Rousseau J, Sackus A, Rollin P, Tatibouët A (2011) Eur J Org Chem 12:2293

    Article  Google Scholar 

  29. Lohse-Fraefel N, Carreira EM (2009) Chem Eur J 15:12065

    Article  CAS  Google Scholar 

  30. Minakata S, Okumura S, Nagamachi T, Takeda Y (2011) Org Lett 13:2966

    Article  CAS  Google Scholar 

  31. Xu L, Yu R, Wang Y, Chen J, Yang Z (2013) J Org Chem 78:5744

    Article  CAS  Google Scholar 

  32. Shintani R, Takagi C, Ito T, Naito M, Nozaki K (2015) Angew Chem Int Ed 54:1616

    Article  CAS  Google Scholar 

  33. Karmakar R, Yun SY, Chen J, Xia Y, Lee D (2015) Angew Chem Int Ed 54:6582

    Article  CAS  Google Scholar 

  34. Xu F, Wang CX, Wang HL, Li XC, Wan BS (2015) Green Chem 17:799

    Article  CAS  Google Scholar 

  35. Xu F, Wang CX, Wang DP, Li XC, Wan BS (2013) Chem Eur J 19:2252

    Article  CAS  Google Scholar 

  36. Perreault S, Rovis T (2009) Chem Soc Rev 38:3149

    Article  CAS  Google Scholar 

  37. Saino N, Amemiya F, Tanabe E, Kase K, Okamoto S (2006) Org Lett 8:1439

    Article  CAS  Google Scholar 

  38. Kelly DR, Baker SC, King DS, de Silva DS, Lord G, Taylor JP (2008) Org Biomol Chem 6:787

    Article  CAS  Google Scholar 

  39. Yu ZX, Caramella P, Houk KN (2003) J Am Chem Soc 125:15420

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to the support from the Startup Fund for PhDs of Natural Scientific Research of Zhengzhou University of Light Industry (to X.F.) and Key Projects of Colleges and Universities in Henan Province (No. 17A150053).

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Authors and Affiliations

  1. Henan Provincial Key Lab of Surface and Interface Science, Zhengzhou University of Light Industry, Zhengzhou, 450002, Henan, People’s Republic of China

    Fen Xu, Wei-Fen Kang, Xiao-Ning Wang, Ying-Ying Zhu, San-Xu Chen, Yue-Jie Kong & Shao-Ming Fang

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  1. Fen Xu
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  2. Wei-Fen Kang
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  3. Xiao-Ning Wang
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  4. Ying-Ying Zhu
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  7. Shao-Ming Fang
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Correspondence to Fen Xu.

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Xu, F., Kang, WF., Wang, XN. et al. Hypervalent iodine-induced formation of 3,5-disubstituted isoxazoles via [3 + 2] cycloaddition of diynes with aldoximes. Monatsh Chem 148, 1109–1116 (2017). https://doi.org/10.1007/s00706-016-1907-3

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  • DOI: https://doi.org/10.1007/s00706-016-1907-3

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