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Triphenylphosphine-mediated chemoselective synthesis of functionalized thiazol-2(5H)-ones

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Abstract

Stabilized phosphoranes, obtained from three-component reaction between dialkyl acetylenedicarboxylates and thiazolidine-2,4-dione in the presence of triphenylphosphine, undergo a smooth intramolecular Wittig reaction in boiling toluene to produce functionalized thiazol-2(5H)-ones in good yields. When alkyl propiolates were employed in these reactions, only the (E)-isomer of alkyl 3-(2,4-dioxothiazolidin-3-yl)acrylates were isolated. A dynamic effect was observed in the 1H nuclear magnetic resonance (NMR) spectrum of ethyl (E)-3-(2,4-dioxothiazolidin-3-yl)-3-phenylacrylate as a result of restricted rotation (∆G ≠ = 77 kJ/mol) around the N–C bond between the thiazolidine moiety and the vinyl group.

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References

  1. Lewis JR (1996) Nat Prod Rep 13:435

    Article  CAS  Google Scholar 

  2. Metzger JV (1979) Thiazole and its Derivatives. Wiley, New York

    Google Scholar 

  3. Kiryanov AA, Sampson P, Seed AJ (2001) J Org Chem 66:7925

    Article  CAS  Google Scholar 

  4. Bach T, Heuser S (2000) Tetrahedron Lett 41:1707

    Article  CAS  Google Scholar 

  5. Potewar TM, Ingale SA, Srinivasan KV (2007) Tetrahedron 63:11066

    Article  CAS  Google Scholar 

  6. Zambon A, Borsato G, Brussolo S, Frascella P, Lucchini V (2008) Tetrahedron Lett 49:66

  7. Franklin PX, Pillai AD, Rathod PD, Yerande S, Nivsarkar M, Padh H, Vasu KK, Sudarsanam V (2008) Eur J Med Chem 43:129

    Article  CAS  Google Scholar 

  8. Karegoudar P, Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumari NS (2008) Eur J Med Chem 43:261

    Article  CAS  Google Scholar 

  9. Ochiai M, Nishi Y, Hashimoto S, Tsuchimoto Y, Chen DW (2003) J Org Chem 68:7887

    Article  CAS  Google Scholar 

  10. Yavari I, Hajinasiri R, Sayyed-Alangi SZ, Iravani N (2008) Monatsh Chem 139:1029

    Article  CAS  Google Scholar 

  11. Yavari I, Nematpour M, Hossaini Z (2010) Monatsh Chem 141:229

    Article  CAS  Google Scholar 

  12. Yavari I, Sanaeishoar T, Ghazvini M, Iravani N (2010) J Sulfur Chem 31:169

    Article  CAS  Google Scholar 

  13. Ramazani A, Kazemizadeh AR, Ahmadi E, Noshiranzadeh N, Souldozi A (2008) Curr Org Chem 12:59

    Article  CAS  Google Scholar 

  14. Yavari I, Zabarjad-Shiraz N, Maghsoodlou MT, Hazeri N (2002) Phosphorus Sulfur Silicon Relat Elem 177:759

    Article  CAS  Google Scholar 

  15. Yavari I, Zabarjad-Shiraz N (2004) Phosphorus. Sulfur Silicon Relat Elem 179:1477

    Article  CAS  Google Scholar 

  16. Yavari I, Zabarjad-Shiraz N (2003) Monatsh Chem 134:445

    CAS  Google Scholar 

  17. Eliel EL, Wilen SH (1994) Stereochemistry of Organic Compounds. Wiley, New York, p 569

    Google Scholar 

  18. Günther H (1995) NMR Spectroscopy, 2nd ed, Wiley, New York, Chapter 9

  19. Bruno G, Costantino L, Curinga C, Maccari R, Monforte F, Nicolo F, Ottana R, Vigorita MG (2002) Bioorg Med Chem 10:1077

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, Science and Research Branch, Islamic Azad University, Ponak, Tehran, Iran

    Issa Yavari, Leila Azad & Tayebeh Sanaeishoar

Authors
  1. Issa Yavari
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  2. Leila Azad
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  3. Tayebeh Sanaeishoar
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Correspondence to Issa Yavari.

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Yavari, I., Azad, L. & Sanaeishoar, T. Triphenylphosphine-mediated chemoselective synthesis of functionalized thiazol-2(5H)-ones. Monatsh Chem 142, 177–182 (2011). https://doi.org/10.1007/s00706-010-0434-x

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  • DOI: https://doi.org/10.1007/s00706-010-0434-x

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