Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Metal-Free Conversion of Carboxamides to Ureas Using Tertiary Amines and Iodosylmesitylene

  • Han, Hoon (Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST)) ;
  • Chang, Suk-Bok (Department of Chemistry and Molecular-Level Interface Research Center, Korea Advanced Institute of Science and Technology (KAIST))
  • Published : 2010.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035. https://doi.org/10.1021/cr950083f
  2. Spanu, P.; Ulgheri, F. Curr. Org. Chem. 2008, 12, 1071. https://doi.org/10.2174/138527208785740319
  3. Zakrzewski, J.; Krawczyk, M. Heteroatom Chem. 2006, 17, 393. https://doi.org/10.1002/hc.20228
  4. Klingstedt, F.; Arve, K.; Eranen, K.; Murzin, D. Y. Acc. Chem. Res. 2006, 39, 273. https://doi.org/10.1021/ar050185k
  5. Das, J.; Lin, J.; Moquin, R. V.; Shen, Z.; Spergel, S. H.; Wityak, J.; Doweyko, A. M.; DeFex, H. F.; Fang, Q.; Pang, S.; Pitt, S.; Shen, D. R.; Schieven, G. L.; Barrish, J. C. Bioorg. Med. Chem. Lett. 2003, 13, 2145. https://doi.org/10.1016/S0960-894X(03)00380-9
  6. Kurihara, M.; Rouf, A. S. S.; Kansui, H.; Kagechika, H.; Okuda, H.; Miyata, N. Bioorg. Med. Chem. Lett. 2004, 14, 4131. https://doi.org/10.1016/j.bmcl.2004.06.038
  7. Christianson, D. W. Acc. Chem. Res. 2005, 38, 191. https://doi.org/10.1021/ar040183k
  8. Doyle, A. J.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713. https://doi.org/10.1021/cr068373r
  9. Zhang, Z.; Schreiner, P. R. Chem. Soc. Rev. 2009, 38, 1187. https://doi.org/10.1039/b801793j
  10. Bell, T. W.; Hext, N. M. Chem. Soc. Rev. 2004, 33, 589.
  11. Amendola, V.; Esteban-Gómez, D.; Fabbrizzi, L.; Licchelli, M. Acc. Chem. Res. 2006, 39, 343. https://doi.org/10.1021/ar050195l
  12. Borovik, A. S. Acc. Chem. Res. 2005, 38, 54. https://doi.org/10.1021/ar030160q
  13. Petersen, U. In Methoden der Organischen Chemie: Houben-Weyl; E4; G. Thieme Verlag: New York, 1983; pp 334.
  14. Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. https://doi.org/10.1021/jo00086a061
  15. Barrett, A. G. M.; Betts, M. J.; Fenwick, A. J. Org. Chem. 1985, 50, 169. https://doi.org/10.1021/jo00202a006
  16. Wang, Y.; Wheelhouse, R. T.; Zhao, L.; Langnel, D. A. F.; Stevens, M. F. G. J. Chem. Soc., Perkin Trans. 1 1998, 1669.
  17. Basha, A. Tetrahedron Lett. 1988, 29, 2525. https://doi.org/10.1016/S0040-4039(00)86102-X
  18. Matsumura, Y.; Satoh, Y.; Onomura, O.; Maki, T. J. Org. Chem. 2000, 65, 1549. https://doi.org/10.1021/jo991076k
  19. Aguirre, I. de; Collot, J. Bull. Soc. Chim. Belg. 1989, 98, 19.
  20. Grupte, S. P.; Chaudhari, R. V. J. Catal. 1988, 114, 246. https://doi.org/10.1016/0021-9517(88)90028-0
  21. Shi, F.; Deng, Y.; SiMa, T.; Yang, H. Tetrahedron Lett. 2001, 42, 2161. https://doi.org/10.1016/S0040-4039(01)00124-1
  22. Gabriele, B.; Salerno, G.; Mancuso, R.; Costa, M. J. Org. Chem. 2004, 69, 4741. https://doi.org/10.1021/jo0494634
  23. Mulla, S. A. R.; Rode, C. V.; Kelkar, A. A.; Gupte, S. P. J. Mol. Catal. A. Chem. 1997, 122, 103. https://doi.org/10.1016/S1381-1169(97)00023-X
  24. Bassoli, A.; Rindone, B.; Tollari, S.; Chioccara, F. J. Mol. Catal. 1990, 60, 41. https://doi.org/10.1016/0304-5102(90)85065-P
  25. Dombek, B. D.; Angelici, R. J. J. Organomet. Chem. 1977, 134, 203. https://doi.org/10.1016/S0022-328X(00)81420-5
  26. Sonoda, N.; Yasuhara, T.; Kondo, K.; Ikeda, T.; Tsutsumi, S. J. Am. Chem. Soc. 1971, 93, 6344. https://doi.org/10.1021/ja00752a099
  27. Yoshida, T.; Kambe, N.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1986, 27, 2037. https://doi.org/10.1016/S0040-4039(00)84442-1
  28. Sonoda, N. Pure Appl. Chem. 1993, 65, 699. https://doi.org/10.1351/pac199365040699
  29. McCusker, J. E.; Main, A. D.; Johnson, K. S.; Grasso, C. A.; McElwee-White, L. J. Org. Chem. 2000, 65, 5216. https://doi.org/10.1021/jo000364+
  30. McCusker, J. E.; Qian, F.; McElwee-White, L. J. Mol. Catal. A-Chem. 2000, 159, 11. https://doi.org/10.1016/S1381-1169(00)00164-3
  31. Han, H.; Bae, I.; Yoo, E. J.; Lee, J.; Do, Y.; Chang, S. Org. Lett. 2004, 6, 4109. https://doi.org/10.1021/ol0481784
  32. Bae, I.; Han, H.; Chang, S. J. Am. Chem. Soc. 2005, 127, 2038. https://doi.org/10.1021/ja0432968
  33. Cho. S. H.; Yoo, E. J.; Bae, I.; Chang. S. J. Am. Chem. Soc. 2005, 127, 16046. https://doi.org/10.1021/ja056399e
  34. Yoo. E. J.; Bae, I.; Cho, S. H.; Han, H.; Chang, S. Org. Lett. 2006, 8, 1347. https://doi.org/10.1021/ol060056j
  35. Chang, S.; Lee, M. J.; Jung, D. Y.; Yoo, E. J.; Cho, S. H.; Han, S. K. J. Am. Chem. Soc. 2006, 128, 12366. https://doi.org/10.1021/ja064788i
  36. Han, H.; Park, S. B.; Kim, S. K.; Chang. S. J. Org. Chem. 2008, 73, 2862. https://doi.org/10.1021/jo800134j
  37. Brewster, J. H.; Eliel, E. L. In Organic Reactions; Adams, R., Ed.; John Wiley and Sons: New York, 1953; Vol. VII, pp 142.
  38. Olofoson, R. A.; Schur, R. C.; Bunes, L.; Pepe, J. P. Tetrahedron Lett. 1977, 18, 1567. https://doi.org/10.1016/S0040-4039(01)93104-1
  39. Cooley, J. H.; Evain, E. J. Synthesis 1989, 1.
  40. Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. https://doi.org/10.1021/ja017076v
  41. Ko, S.; Lee, C.; Choi, M.-G.; Na, Y.; Chang, S. J. Org. Chem. 2003, 68, 1607. https://doi.org/10.1021/jo026591o
  42. Ko, S.; Han, H.; Chang, S. Org. Lett. 2003, 5, 2687. https://doi.org/10.1021/ol034862r
  43. Na, Y.; Ko, S.; Hwang, L. K.; Chang, S. Tetrahedron Lett. 2003, 44, 4475. https://doi.org/10.1016/S0040-4039(03)01016-5
  44. Ko, S.; Kang, B.; Chang, S. Angew. Chem., Int. Ed. 2005, 44, 455. https://doi.org/10.1002/anie.200462006
  45. Park, E. J.; Lee, J. M.; Han, H.; Chang, S. Org. Lett. 2006, 8, 4355. https://doi.org/10.1021/ol061753e
  46. Trost, B. M. In Comprehensive Oganic Synthesis; Pergamon: Oxford, 1991; pp 795.
  47. Abdul Hai, S. M.; Perveen, S.; Khan, R. A.; Khan, K. M.; Afza, N. Nat. Prod. Res. 2003, 17, 351. https://doi.org/10.1080/1057563031000072613
  48. Aranha, R. M.; Bowser, A. M.; Madalengoitia, J. S. Org. Lett. 2009, 11, 575. https://doi.org/10.1021/ol802577z
  49. Okazaki, R.; Tokitoh, N. J. Chem. Soc., Chem. Commun. 1984, 192.
  50. Monkovic, I.; Wong, H.; Bachand, C. Synthesis 1985, 770.

Cited by

  1. Highly Efficient Synthesis of Ureas and Carbamates from Amides by Iodosylbenzene-Induced Hofmann Rearrangement vol.2012, pp.10, 2012, https://doi.org/10.1002/ejoc.201101784
  2. ChemInform Abstract: Metal-Free Conversion of Carboxamides to Ureas Using Tertiary Amines and Iodosylmesitylene. vol.41, pp.31, 2010, https://doi.org/10.1002/chin.201031090