Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Trichloroisocyanuric Acid as a Novel and Versatile Reagent for the Rapid α-Thiocyanation of Ketones

  • Liu, Shanshan (The First Affiliated Hospital, Xinxiang Medical University) ;
  • Guo, Zhihao (The Third Affiliated Hospital, Xinxiang Medical University) ;
  • Wang, Yaqin (The First Affiliated Hospital, Xinxiang Medical University) ;
  • Wang, Tianbao (The First Affiliated Hospital, Xinxiang Medical University) ;
  • Wu, Liqiang (School of Pharmacy, Xinxiang Medical University)
  • Received : 2011.06.02
  • Accepted : 2011.08.07
  • Published : 2011.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Nguyen, T.; Rubinstein, M.; Wakselman, C. J. Org. Chem. 1981, 46, 1938. https://doi.org/10.1021/jo00322a047
  2. Grieco, P. A.; Yokoyama, Y.; Williams, E. J. Org. Chem. 1978, 43, 1283. https://doi.org/10.1021/jo00400a070
  3. Riemschneider, R.; Wojahn, F.; Orlick, G. J. Am. Chem. Soc. 1951, 73, 5905.
  4. Lee, Y. T.; Choi, S. Y.; Chung, Y. K. Tetrahedron Lett. 2007, 48, 5673. https://doi.org/10.1016/j.tetlet.2007.06.041
  5. Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951. https://doi.org/10.1016/j.tetlet.2004.02.073
  6. Wood, J. L. In Organic Reactions; Adams, R., Ed.; John Wiley and Sons: New York, 1946; Vol. 3, Chapter 6.
  7. Guy, R. G. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; John Wiley & Sons: New York, 1977; Part 2, Chapter 18, p 819.
  8. Prakash, O.; Saini, N. Synth. Commun. 1993, 23, 1455. https://doi.org/10.1080/00397919308011236
  9. Dittmer, D. C. Comprehensive Heterocyclic Chemistry; Vol. 7, Katritzky, A., Ed.; Pergamon: Oxford, 1984; p 178.
  10. Bhalerao, D. S.; Akamanchi, K. G.. Synth. Commun. 2010, 40, 799. https://doi.org/10.1080/00397910902838938
  11. Kumar, M. A.; Reddy, K. R. K. K.; Reddy, M. V.; Reddy, C. S.; Reddy, C. D. Synth. Commun. 2008, 38, 2089. https://doi.org/10.1080/00397910802029349
  12. Chaskar, A. C.; Yadav, A. A.; Langi, B. P.; Murugappan, A.; Shah, C. Synth. Commun. 2010, 40, 2850. https://doi.org/10.1080/00397910903320639
  13. Prakash, O.; Kaur, H.; Batra, H.; Rani, N.; Singh, S. P.; Moriarty, R. M. J. Org. Chem. 2001, 66, 2019. https://doi.org/10.1021/jo001504i
  14. Maurya, R. A.; Kumar, A.; Ahamd, P. Tetrahedron Lett. 2007, 48, 1399. https://doi.org/10.1016/j.tetlet.2006.12.103
  15. Yadav, J. S.; Reddy, B. V. S.; Reddy, U. V. S.; Krishna, A. D. Tetrahedron Lett. 2007, 48, 5243. https://doi.org/10.1016/j.tetlet.2007.05.143
  16. Xiong, Z.-X.; Huang, N.-P.; Zhong, P. Synth. Commun. 2001, 31, 245. https://doi.org/10.1081/SCC-100000205
  17. Zolfigol, M. A.; Azarifar, D.; Maleki, B. Tetrahedron Lett. 2004, 45, 2181. https://doi.org/10.1016/j.tetlet.2004.01.038
  18. Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. Synth. Commun. 2004, 34, 3623. https://doi.org/10.1081/SCC-200031053
  19. Acharya, J.; Gupta, A. K.; Shakya, P. D.; Kaushik, M. P. Tetrahedron Lett. 2005, 46, 5293. https://doi.org/10.1016/j.tetlet.2005.06.024
  20. Shirini, F.; Zolfigol, M. A.; Mollarazi, E. Lett. Org. Chem. 2005, 2, 718. https://doi.org/10.2174/157017805774717445
  21. Zolfigol, M. A.; Khazaei, A.; Choghamarani, A. G.; Rostami, A.; Hajjami, M. Catal. Commun. 2006, 7, 399. https://doi.org/10.1016/j.catcom.2005.12.004
  22. Khazaei, A.; Zolfigol, M. A.; Rostami, A.; Choghamarani, A. G. Catal. Commun. 2007, 8, 543. https://doi.org/10.1016/j.catcom.2006.06.018
  23. Bigdeli, M. A.; Jafari, S.; Mahdavinia, G. H.; Hazarkhani, H. Catal. Commun. 2007, 8, 1641. https://doi.org/10.1016/j.catcom.2007.01.022
  24. Bigdeli, M. A.; Nemati, F.; Mahdavinia, Gholam H.; Doostmohammadi, H. Chin. Chem. Lett. 2009, 20, 1275. https://doi.org/10.1016/j.cclet.2009.06.024
  25. Veisi, H.; Gholbedaghi, R.; Malakootikhah, J.; Sedrpoushan, A.; Maleki, B.; Kordestani, D. J. Heterocyclic Chem. 2010, 47, 1398. https://doi.org/10.1002/jhet.486

Cited by

  1. ChemInform Abstract: Trichloroisocyanuric Acid as a Novel and Versatile Reagent for the Rapid α-Thiocyanation of Ketones. vol.43, pp.9, 2012, https://doi.org/10.1002/chin.201209087
  2. α-thiocyanation of carbonyl compounds: A review vol.47, pp.2, 2017, https://doi.org/10.1080/00397911.2016.1255973
  3. Ag/Pyridine Co-Mediated Oxidative Arylthiocyanation of Activated Alkenes vol.23, pp.10, 2018, https://doi.org/10.3390/molecules23102727
  4. Synthesis of ionic liquid-supported hypervalent iodine reagent and its application as a `catch and release' reagent for a-substituted acetophenones vol.4, pp.27, 2014, https://doi.org/10.1039/c4ra00063c
  5. Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N-Thiocyanatophthalimide vol.20, pp.6, 2011, https://doi.org/10.1021/acs.orglett.8b00342
  6. α-Selective C(sp3)-H Thio/Selenocyanation of Ketones with Elemental Chalcogen vol.86, pp.23, 2011, https://doi.org/10.1021/acs.joc.1c02431