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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 3, pp 375–378 | Cite as

Pd/Cu-assisted C–S activation and N–H insertion: highly versatile synthesis of 2-aminopyrimidines from 3,4-dihydropyrimidine-2(1H)-thiones

  • Hina Mathur
  • Mohammed Shahrukh Khan Zai
  • Poonam Khandelwal
  • Neetu Kumari
  • Ved Prakash Verma
  • Dinesh Kumar YadavEmail author
Article
  • 148 Downloads

A method for the synthesis of 2-aminopyrimidines from readily available 3,4-dihydropyrimidine-2(1H)-thiones via a palladium-assisted C–S activation and N–H insertion reaction is developed. The process provides an access to a variety of highly diverse 2-aryl(alkyl)-aminopyrimidine adducts in good yields.

Keywords

2-aminopyrimidines Biginelli reaction C–S activation N–H insertion 

Notes

The study was performed with financial support from the SERB, DST-India (project No. ECR/2017/001254).

References

  1. 1.
    Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.CrossRefGoogle Scholar
  2. 2.
    Villalobos, J. M.; Srogl, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2007, 129, 15734.CrossRefPubMedPubMedCentralGoogle Scholar
  3. 3.
    Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2000, 2, 3229.CrossRefPubMedGoogle Scholar
  4. 4.
    Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91.CrossRefPubMedGoogle Scholar
  5. 5.
    Prokopcová, H.; Kappe, C. O. Angew. Chem., Int. Ed. 2009, 48, 2276.Google Scholar
  6. 6.
    Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599.CrossRefPubMedGoogle Scholar
  7. 7.
    Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979.CrossRefPubMedGoogle Scholar
  8. 8.
    Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69, 3554.CrossRefPubMedGoogle Scholar
  9. 9.
    Prokopcová, H.; Kappe, C. O. J. Org. Chem. 2007, 72, 4440.CrossRefPubMedGoogle Scholar
  10. 10.
    Lengar, A.; Kappe, C. O. Org. Lett. 2004, 6, 771.CrossRefPubMedGoogle Scholar
  11. 11.
    Silva, S.; Sylla, B.; Suzenet, F.; Tatibouët, A.; Rauter, A. P.; Rollin, P. Org. Lett. 2008, 10, 853.CrossRefPubMedGoogle Scholar
  12. 12.
    Silva, S.; Tardy, S.; Routier, S.; Suzenet, F.; Tatibouët, A.; Rauter, A. P.; Rollin, P. Tetrahedron Lett. 2008, 49, 5583.CrossRefGoogle Scholar
  13. 13.
    Arshad, N.; Hashim, J.; Kappe, C. O. J. Org. Chem. 2009, 74, 5118.CrossRefPubMedGoogle Scholar
  14. 14.
    Sun, Q.; Suzenet, F.; Guillaumet, G. J. Org. Chem. 2010, 75, 3473.CrossRefPubMedGoogle Scholar
  15. 15.
    Sun, Q.; Suzenet, F.; Guillaumet, G. Tetrahedron Lett. 2012, 53, 2694.CrossRefGoogle Scholar
  16. 16.
    Jiang, L.; Lu, X.; Zhang, H.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 4542.CrossRefPubMedGoogle Scholar
  17. 17.
    Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 10028.CrossRefPubMedGoogle Scholar
  18. 18.
    Lee, D.-Y.; Hartwig, J. F. Org. Lett. 2005, 7, 1169.CrossRefPubMedGoogle Scholar
  19. 19.
    Xia, N.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 337.CrossRefGoogle Scholar
  20. 20.
    Phan, N. H. T.; Kim, H.; Shin, H.; Lee, H.-S; Sohn, J.-H. Org. Lett. 2016, 18, 5154.CrossRefPubMedGoogle Scholar
  21. 21.
    Kim, J.; Chang, S. Chem. Commun. 2008, 26, 3052.CrossRefGoogle Scholar
  22. 22.
    Perry, N. B.; Ettouati, L.; Litaudon, M.; Blunt, J. W; Munro, M. H. G.; Parkin, S.; Hope, H. Tetrahedron 1994, 50, 3987.CrossRefGoogle Scholar
  23. 23.
    Fresneda, P. M.; Molina, P.; Delgado, S.; Bleda, J. A. Tetrahedron Lett. 2000, 41, 4777.CrossRefGoogle Scholar
  24. 24.
    Mendiola, J.; Minguez, J. M.; Alvarez-Builla, J.; Vaquero, J. J. Org. Lett. 2000, 2, 3253.CrossRefPubMedGoogle Scholar
  25. 25.
    Anderson, R. J.; Morris, J. C. Tetrahedron Lett. 2001, 42, 311.CrossRefGoogle Scholar
  26. 26.
    Álvarez, M.; Fernández, D.; Joule, J. A. Tetrahedron Lett. 2001, 42, 315.CrossRefGoogle Scholar
  27. 27.
    Anderson, R. J.; Morris, J. C. Tetrahedron Lett. 2001, 42, 8697.CrossRefGoogle Scholar
  28. 28.
    Franco, L. H.; Joffé, E. B. D. K., J. E.; Puricelli, L.; Tatian, M.; Seldes, A. M.; Palermo, J. A. J. Nat. Prod. 1998, 61, 1130.Google Scholar
  29. 29.
    Fresneda, P. M.; Molina, P.; Bleda, J. A. Tetrahedron 2001, 57, 2355.CrossRefGoogle Scholar
  30. 30.
    Watanabe, M.; Koike, H.; Ishiba, T.; Okada, T.; Seo, S.; Hirai, K. Bioorg. Med. Chem. 1997, 5, 437.CrossRefPubMedGoogle Scholar
  31. 31.
    Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Nat. Rev. Drug. Discovery 2002, 1, 493.CrossRefPubMedGoogle Scholar
  32. 32.
    Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.CrossRefPubMedGoogle Scholar
  33. 33.
    Wan, J.-P.; Liu, Y. Synthesis 2010, 23, 3943.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Hina Mathur
    • 1
  • Mohammed Shahrukh Khan Zai
    • 1
  • Poonam Khandelwal
    • 1
  • Neetu Kumari
    • 1
  • Ved Prakash Verma
    • 2
  • Dinesh Kumar Yadav
    • 1
    Email author
  1. 1.Department of ChemistryMohanlal Sukhadia UniversityUdaipurIndia
  2. 2.Department of ChemistryBanasthali UniversityTonkIndia

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