Advertisement

Monatshefte für Chemie - Chemical Monthly

, Volume 151, Issue 1, pp 79–85 | Cite as

A copper-catalyzed multicomponent reaction for the synthesis of thioamide skeletons

  • Mehdi KhalajEmail author
Original Paper
  • 88 Downloads

Abstract

In this report, in situ generated sulfide has been reacted with sulfonylketimine derived from the reaction of alkynes and sulfonyl azides by the action of copper salts to form a wide range of thioamide derivatives. Various terminal alkynes including aromatic, heteroaromatic, and aliphatic alkynes have been well tolerated and the reaction also shows good generality along with azides.

Graphic abstract

Keywords

Sulfonylketimine 1,8-Diazabicyclo[5.4.0]undec-7-ene Carbon disulfide Sulfonyl azide Terminal alkyne 

Notes

References

  1. 1.
    DeKorver KA, Johnson WL, Zhang Y, Hsung RP, Dai H, Deng J, Lohse AG, Zhang Y (2011) J Org Chem 76:5092CrossRefGoogle Scholar
  2. 2.
    Mermerian AH, Fu GC (2005) Angew Chem Int Ed 44:949CrossRefGoogle Scholar
  3. 3.
    Ruiz J, Gonzalo MP, Vivanco M, Diaz MR, Garcia-Granda S (2011) Chem Commun 47:4270CrossRefGoogle Scholar
  4. 4.
    Alajarin M, Ortin MM, Sanchez-Andrada P, Vidal A (2006) J Org Chem 71:8126CrossRefGoogle Scholar
  5. 5.
    Alajarin M, Vidal A, Ortin MM (2003) Org Biomol Chem 1:4282CrossRefGoogle Scholar
  6. 6.
    Staudinger H, Hauser E (1921) Helv Chim Acta 4:887CrossRefGoogle Scholar
  7. 7.
    Cho SH, Yoo EJ, Bae I, Chang S (2005) J Am Chem Soc 127:16046CrossRefGoogle Scholar
  8. 8.
    Yoo EJ, Ahlquist M, Kim SH, Bae I, Fokin VV, Sharpless KB, Chang S (2007) Angew Chem Int Ed 46:1730CrossRefGoogle Scholar
  9. 9.
    Yoo EJ, Ahlquist M, Bae I, Sharpless KB, Fokin VV, Chang S (2008) J Org Chem 73:5520CrossRefGoogle Scholar
  10. 10.
    Hwang SJ, Cho SH, Chang S (2008) Pure Appl Chem 80:873CrossRefGoogle Scholar
  11. 11.
    Cassidy MP, Raushel J, Fokin VV (2006) Angew Chem Int Ed 45:3154CrossRefGoogle Scholar
  12. 12.
    Bae I, Han H, Chang S (2005) J Am Chem Soc 127:2038CrossRefGoogle Scholar
  13. 13.
    Yoo EJ, Bae I, Cho SH, Han H, Chang S (2006) Org Lett 8:1347CrossRefGoogle Scholar
  14. 14.
    Yavari I, Ahmadian S, Ghazanfarpour-Darjani M, Solgi Y (2011) Tetrahedron Lett 52:668CrossRefGoogle Scholar
  15. 15.
    Yavari I, Ghazanfarpour-Darjani M, Bayat MJ, Malekafzali A (2014) Synlett 25:959CrossRefGoogle Scholar
  16. 16.
    Yavari I, Ghazanfarpour-Darjani M, Nematpour M (2015) Tetrahedron Lett 56:2416CrossRefGoogle Scholar
  17. 17.
    Khalaj M, Ghazanfarpour-Darjani M, Barat-Seftejani F, Nouri A (2017) Synlett 28:1445CrossRefGoogle Scholar
  18. 18.
    Yoo EJ, Chang S (2008) Org Lett 10:1163CrossRefGoogle Scholar
  19. 19.
    Cui SL, Wang J, Wang YG (2007) Org Lett 9:5023CrossRefGoogle Scholar
  20. 20.
    Whiting M, Fokin VV (2006) Angew Chem Int Ed 45:3157CrossRefGoogle Scholar
  21. 21.
    Yavari I, Nematpour M, Ghazanfarpour-Darjani M (2012) Tetrahedron Lett 53:942CrossRefGoogle Scholar
  22. 22.
    Vlasse M, Giandinoto S, Attarwala ST, Okamoto Y, Emge TJ (1986) Acta Crystallogr C42:487Google Scholar
  23. 23.
    Zhao P, Yin H, Gao H, Xi C (2013) J Org Chem 78:5001CrossRefGoogle Scholar
  24. 24.
    Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Young Researchers and Elite Club, Buinzahra BranchIslamic Azad UniversityBuinzahraIran

Personalised recommendations