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Novel task-specific ionic liquid for room temperature synthesis of spiro-1,2,4-triazolidine-3-thiones

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Abstract

An efficient, novel, task-specific ionic liquid, [2-hydroxymethylpyridinium butanesulfonic acid]HSO4 has been designed for the rapid synthesis of spiro-1,2,4-triazolidine-3-thiones from isatins and thiosemicarbazides in water as an universal solvent at room temperature. The hydroxymethyl functionality tethered to pyridinium nucleus facilitates the reaction in water. This is the first method proceeded at room temperature for synthesis of spiro-1,2,4-triazolidine-3-thiones. The novelty of the method is synthesis of novel task-specific ionic liquid, energy efficiency, atom economy, wide substrate scope, shorter reaction time, high yield of products, and use of water along with ionic liquid are greener aspects of present method.

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References

  1. Dicks AP (2009) Green Chem Lett Rev 2:9

    Article  CAS  Google Scholar 

  2. Azizi N, Aryanasab F, Torkiyan L, Ziyaei A, Saidi MR (2006) J Org Chem 71:3634

    Article  CAS  Google Scholar 

  3. Pore DM, Hegade PG, Gaikwad DS, Patil PB, Patil JD (2014) Lett Org Chem 11:131

    Article  CAS  Google Scholar 

  4. Li C, Chen L (2006) Chem Soc Rev 35:68

    Article  Google Scholar 

  5. Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB (2005) Angew Chem Int Ed 44:3275

    Article  CAS  Google Scholar 

  6. Bao W, Wang Z (2006) Green Chem 8:1028

    Article  CAS  Google Scholar 

  7. Appell R, Gala D, Sanghvi YS (2011) Org Process Res Dev 15:898

    Article  CAS  Google Scholar 

  8. Kotadia DA, Soni SS (2012) J Mol Catal A: Chem 353:44

    Article  Google Scholar 

  9. Fang D, Zhou XL, Ye ZW, Liu ZL (2006) Ind Eng Chem Res 45:7982

    Article  CAS  Google Scholar 

  10. Leng Y, Wang J, Zhu D, Ren X, Ge H, Shen L (2009) Angew Chem Int Ed 48:168

    Article  CAS  Google Scholar 

  11. Holbrey JD, Turner MB, Reichert WM, Rogers RD (2003) Green Chem 5:731

    Article  CAS  Google Scholar 

  12. Wamhoff H (1984) In: Katritzky AR, Rees CW (eds) Comprehensive Heterocyclic Chemistry, vol 5. Pergamon Press, Oxford, p 669

    Chapter  Google Scholar 

  13. Buckle DR, Rockell CJM (1982) J Chem Soc Perkin Trans 1:627

    Article  Google Scholar 

  14. Buckle DR, Outred DJ, Rockell CJM, Smith H, Spicer BA (1983) J Med Chem 26:251

    Article  CAS  Google Scholar 

  15. Buckle DR, Rockell CJM, Smith H, Spicer BA (1986) J Med Chem 29:2269

    Article  Google Scholar 

  16. Alvarez R, Velazquez S, Felix AS, Aquaro S, Clercq ED, Perno CF, Karlsson A, Balzarini J, Camarasa MJ (1994) J Med Chem 37:4185

    Article  CAS  Google Scholar 

  17. Genin MJ, Allwine DA, Anderson DJ, Barbachyn MR, Emmert DE, Garmon SA, Graber DR, Grega KC, Hester JB, Hutchinson DK, Morris J, Reischer RJ, Ford CW, Zurenko GE, Hamel JC, Schaadt RD, Stapert D, Yagi BH (2000) J Med Chem 43:953

    Article  CAS  Google Scholar 

  18. Brockunier LL, Parmee ER, Ok HO, Candelore MR, Cascieri MA, Colwell LF, Deng L, Feeney WP, Forrest MJ, Hom GJ, MacIntyre DE, Tota L, Wywratt MJ, Fisher MH, Weber AE (2000) Bioorg Med Chem Lett 10:2111

    Article  CAS  Google Scholar 

  19. Küçükgüzel SG, Çıkla-Süzgün P (2015) Eur J Med Chem 97:830

    Article  Google Scholar 

  20. Pore DM, Hegade PG, Mane MM, Patil JD (2013) RSC Adv 3:25723

    Article  CAS  Google Scholar 

  21. Rathinam R, Appaswami L (2015) RSC Adv 5:51188

    Article  Google Scholar 

  22. Patil PB, Patil JD, Korade SN, Kshirsagar SD, Govindwar SP, Pore DM (2015) Res Chem Intermed. doi:10.1007/s11164-015-2267-z

    Google Scholar 

  23. Patil JD, Pore DM (2014) RSC Adv 4:14314

    Article  CAS  Google Scholar 

  24. Patil JD, Korade SN, Patil SA, Gaikwad DS, Pore DM (2015) RSC Adv 5:79061

    Article  CAS  Google Scholar 

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Acknowledgments

The authors DMP and SNK thank the DST Fast Track Scheme, New Delhi for financial assistance [No. SB/FT/CS-154/2012].

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Authors and Affiliations

  1. Department of Chemistry, Shivaji University, Kolhapur, 416004, India

    Suyog N. Korade, Jayavant D. Patil & Dattaprasad M. Pore

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  1. Suyog N. Korade
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  2. Jayavant D. Patil
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  3. Dattaprasad M. Pore
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Correspondence to Dattaprasad M. Pore.

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Korade, S.N., Patil, J.D. & Pore, D.M. Novel task-specific ionic liquid for room temperature synthesis of spiro-1,2,4-triazolidine-3-thiones. Monatsh Chem 147, 2143–2149 (2016). https://doi.org/10.1007/s00706-016-1740-8

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  • DOI: https://doi.org/10.1007/s00706-016-1740-8

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