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Copper-catalyzed synthesis of thiazolidine derivatives via multicomponent reaction of terminal alkynes, elemental sulfur, and aziridines

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Abstract

An atom-economic catalytic multicomponent reaction between terminal alkynes, elemental sulfur, and aziridines has been reported. In this transformation, alkyne thiolate derived from the reaction of terminal alkynes and elemental sulfur in the presence of CuOTf/DBU reacted with aziridines to afford thiazolidine derivatives.

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References

  1. Li H, Liu J, Yan B, Li Y (2009) Tetrahedron Lett 50:2353

    Article  CAS  Google Scholar 

  2. Yoo WJ, Lia CJ (2008) Adv Synth Catal 350:1503

    Article  CAS  Google Scholar 

  3. Patil NT, Raut VS (2010) J Org Chem 75:6961

    Article  CAS  PubMed  Google Scholar 

  4. Pappo R, Collins PW (1972) Tetrahedron Lett 13:2627

    Article  Google Scholar 

  5. Bruhn M, Brown CH, Collins PW, Palmer JR, Dajani EZ, Pappo R (1976) Tetrahedron Lett 17:235

    Article  Google Scholar 

  6. Schwartz J, Carr DB, Hansen RT, Dayrit FM (1980) J Org Chem 45:3053

    Article  CAS  Google Scholar 

  7. Sinclair JA, Molander GA, Brown HC (1977) J Am Chem Soc 99:954

    Article  CAS  Google Scholar 

  8. Kim S, Lee JM (1990) Tetrahedron Lett 31:7627

    Article  CAS  Google Scholar 

  9. Hooz J, Layton RB (1971) J Am Chem Soc 93:7320

    Article  CAS  Google Scholar 

  10. Zhang X, Zhang WZ, Shi LL, Zhu C, Jiang JL, Lu X (2012) Tetrahedron 68:9085

    Article  CAS  Google Scholar 

  11. Ranjan A, Mandal A, Yerande SG, Dethe DH (2015) Chem Commun 51:14215

    Article  CAS  Google Scholar 

  12. Guo M, Li D, Zhang Z (2003) J Org Chem 68:10172

    Article  CAS  PubMed  Google Scholar 

  13. Meldal M, Tornøe CW (2008) Chem Rev 108:2952

    Article  CAS  PubMed  Google Scholar 

  14. Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV (2009) Angew Chem Int Ed 48:1

    Article  CAS  Google Scholar 

  15. Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004

    Article  CAS  Google Scholar 

  16. Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV (2005) J Am Chem Soc 127:210

    Article  CAS  PubMed  Google Scholar 

  17. Knöpfel TF, Carreira EM (2003) J Am Chem Soc 125:6054

    Article  CAS  PubMed  Google Scholar 

  18. Fischer C, Carreira EM (2001) Org Lett 3:4319

    Article  CAS  PubMed  Google Scholar 

  19. Frantz DE, Fassler R, Carreira EM (2000) J Am Chem Soc 122:1806

    Article  CAS  Google Scholar 

  20. Lu Y, Johnstone TC, Arndtsen BA (2009) J Am Chem Soc 131:11284

    Article  CAS  PubMed  Google Scholar 

  21. Yavari I, Ghazanfarpour-Darjani M, Nematpour M (2015) Tetrahedron Lett 56:2416

    Article  CAS  Google Scholar 

  22. Khalaj M, Ghazanfarpour-Darjani M, Barat-Seftejani F, Nouri A (2017) Synlett 28:1445

    Article  Google Scholar 

  23. Ramanathana D, Pitchumani K (2015) J Org Chem 80:10299

    Article  CAS  Google Scholar 

  24. Lu P, Wang Y (2012) Chem Soc Rev 41:5687

    Article  CAS  PubMed  Google Scholar 

  25. Chauhan DP, Varma SJ, Vijeta A, Banerjee P, Talukdar P (2014) Chem Commun 50:323

    Article  CAS  Google Scholar 

  26. Ghazanfarpour-Darjani M, Babapour-Kooshalshahi M, Mousavi-Safavi SM, Akbari-Neyestani J, Khalaj M (2016) Synlett 27:259

    Article  CAS  Google Scholar 

  27. Samzadeh-Kermani A (2016) Tetrahedron 72:5301

    Article  CAS  Google Scholar 

  28. Samzadeh-Kermani A (2016) Synlett 27:461

    Article  CAS  Google Scholar 

  29. Glaser C (1869) Ber Dtsch Chem Ges 2:422

    Article  Google Scholar 

  30. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596

    Article  CAS  Google Scholar 

  31. Kumaraswamy G, Ankamma K, Pitchaiah A (2007) J Org Chem 72:9822

    Article  CAS  PubMed  Google Scholar 

  32. Ando T, Kano D, Minakata S, Ryu I, Komatsu M (1998) Tetrahedron 54:13485

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Young Researchers and Elite Club, Buinzahra Branch, Islamic Azad University, Buinzahra, Iran

    Mehdi Khalaj, Seyed Mahmoud Mousavi Safavi & Arash Lalegani

  2. Department of Chemistry, Takestan Branch, Islamic Azad University, Takestan, Iran

    Mahdieh Sadeghpour

  3. Department of Chemistry, Faculty of Samen Hojaj, Mashhad Branch, Technical and Vocational University (TVU), Tehran, Iran

    Seyed Mola Khatami

Authors
  1. Mehdi Khalaj
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  2. Mahdieh Sadeghpour
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  3. Seyed Mahmoud Mousavi Safavi
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  4. Arash Lalegani
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  5. Seyed Mola Khatami
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Correspondence to Mehdi Khalaj.

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Khalaj, M., Sadeghpour, M., Mousavi Safavi, S.M. et al. Copper-catalyzed synthesis of thiazolidine derivatives via multicomponent reaction of terminal alkynes, elemental sulfur, and aziridines. Monatsh Chem 150, 1085–1091 (2019). https://doi.org/10.1007/s00706-019-2363-7

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  • DOI: https://doi.org/10.1007/s00706-019-2363-7

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