DOI QR코드

DOI QR Code

Synthesis of N-Azaaryl Anilines: An Efficient Protocol via Smiles Rearrangement

  • Xia, Shuai (College of Pharmaceutical Sciences, Southwest University) ;
  • Wang, Li-Ying (College of Pharmaceutical Sciences, Southwest University) ;
  • Sun, Heng-Zhi (College of Pharmaceutical Sciences, Southwest University) ;
  • Yue, Huan (College of Pharmaceutical Sciences, Southwest University) ;
  • Wang, Xiu-Hua (College of Pharmaceutical Sciences, Southwest University) ;
  • Tan, Jia-Lian (College of Pharmaceutical Sciences, Southwest University) ;
  • Wang, Yin (College of Pharmaceutical Sciences, Southwest University) ;
  • Hou, Di (College of Pharmaceutical Sciences, Southwest University) ;
  • He, Xiao-Yan (College of Pharmaceutical Sciences, Southwest University) ;
  • Mun, Ki-Cheol (College of Pharmaceutical Sciences, Southwest University) ;
  • Kumar, B. Prem (Department of Chemistry, Changwon National University) ;
  • Zuo, Hua (College of Pharmaceutical Sciences, Southwest University) ;
  • Shin, Dong-Soo (Department of Chemistry, Changwon National University)
  • Received : 2012.09.08
  • Accepted : 2012.11.08
  • Published : 2013.02.20

Abstract

An efficient process for the synthesis of N-azaaryl anilines via Smiles rearrangement as a tool. A variety of N-azaaryl anilines were generated by the reaction of substituted phenols, substituted anilines, aminopyridines and chloroacetyl chloride or pyridols, under base condition in good to excellent yields.

Keywords

References

  1. Shetty, R. S.; Lee, Y.; Liu, B.; Husain, A.; Joseph, R. W.; Lu, Y.; Nelson, D.; Mihelcic, J.; Chao, W.; Moffett, K. K.; Schumacher, A.; Flubacher, D.; Stojanovic, A.; Bukhtiyarova, M.; Williams, K.; Lee, K.-J.; Ochman, A. R.; Saporito, M. S.; Moore, W. R.; Flynn, G. A.; Dorsey, B. D.; Springman, E. B.; Fujimoto, T.; Kelly, M. J. J. Med. Chem. 2011, 54, 179. https://doi.org/10.1021/jm100659v
  2. Lakde, S. K.; Somani, R. R.; Agrawal, A. G.; Shirodkar, P. Y. Int. J. Chem. Tech. Res. 2010, 2, 780.
  3. Du, A.; Zhang, S.; Miao, J.; Zhao, B. Exp. Lung Res. 2004, 30(6), 419. https://doi.org/10.1080/01902140490476337
  4. Williams, D. K.; Chen, X.-T.; Tarby, C.; Kaltenbach, R.; Cai, Z.-W.; Tokarski, J. S.; An, Y.; Sack, J. S.; Wautlet, B.; Gullo- Brown, J.; Henley, B. J.; Jeyaseelan, R.; Kellar, K.; Manne, V.; Trainor, G. L.; Lombardo, L. J.; Fargnoli, J.; Borzilleri, R. M. Bioorg. Med. Chem. Lett. 2010, 20, 2998. https://doi.org/10.1016/j.bmcl.2010.01.042
  5. Du, A.; Zhao, B.; Yin, D.; Zhang, S.; Miao, J. Bioorg. Med. Chem. 2006, 16(1), 81. https://doi.org/10.1016/j.bmcl.2005.09.050
  6. Sreenivas, D. K.; Ramkumar, N.; Nagarajan, R. Org. Bio. Chem. 2012, 10, 3417. https://doi.org/10.1039/c2ob07179g
  7. Chu, J. H.; Lin, P. S.; Lee, Y.-M.; Shen, W. T.; Wu, M. J. Chem. Eur. J. 2011, 17, 13613. https://doi.org/10.1002/chem.201101528
  8. Johansson Seechurn, C. C. C.; Parisel, S. L.; Colacot, T. J. J. Org. Chem. 2011, 76, 7918. https://doi.org/10.1021/jo2013324
  9. Maiti, D.; Fors, B. P.; Henderson, J. L.; Nakamura, Y.; Buchwald, S. L. Chem. Sci. 2011, 2, 57. https://doi.org/10.1039/c0sc00330a
  10. Dogan, O.; Demir, S.; Ozdemir, I.; Cetinkaya, B. Appl. Organometal. Chem. 2011, 25, 163. https://doi.org/10.1002/aoc.1731
  11. Demir, S.; Ozdemir, I.; Cetinkaya, B.; Arslan, H.; VanDerveer, D. Polyhedron 2011, 30, 195. https://doi.org/10.1016/j.poly.2010.10.015
  12. Ogata, T.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 13848. https://doi.org/10.1021/ja805810p
  13. Chen, G. S.; Lam, W. H.; Fok, W. S.; Lee, H. W.; Kwong, F. Y. Chem. Asian J. 2007, 2, 306. https://doi.org/10.1002/asia.200600322
  14. Madrid, P. B.; Polgar, W. E.; Toll, L.; Tanga, M. J. Bioorg. Med. Chem. Lett. 2007, 17, 3014. https://doi.org/10.1016/j.bmcl.2007.03.064
  15. Viciu, M. S.; Kelly, R. A.; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479. https://doi.org/10.1021/ol034264c
  16. Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729. https://doi.org/10.1021/jo010613+
  17. Huang, X. H.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653. https://doi.org/10.1021/ja035483w
  18. Huang, M. N.; Lin, X. Q.; Zhu, X. H.; Peng, W. L.; Xie, J. W.; Wan, Y. Q. Eur. J. Org. Chem. 2011, 24, 4523.
  19. Mazu, T. K.; Etukala, J. R.; Jacob, M. R.; Khan, S. I.; Walker, L. A.; Ablordeppey, S. Y. Eur. J. Med. Chem. 2011, 46, 2378. https://doi.org/10.1016/j.ejmech.2011.03.021
  20. Mazu, T. K.; Etukala, J. R.; Zhu, X. Y.; Jacob, M. R.; Khan, S. I.; Walker, L. A.; Ablordeppey, S. Y. Bioorg. Med. Chem. 2011, 19, 524. https://doi.org/10.1016/j.bmc.2010.10.065
  21. Kim, A. Y.; Lee, H. J.; Park, J. C.; Kang, H.; Yang, H.; Song, H.; Park, K. H. Molecules 2009, 14, 5169. https://doi.org/10.3390/molecules14125169
  22. Lin, B. D.; Liu, M. C.; Ye, Z. S.; Ding, J. C.; Wu, H. Y.; Cheng, J. Org. Biomol. Chem. 2009, 7, 869. https://doi.org/10.1039/b819510b
  23. Liu, Y.; Bai, Y.; Zhang, J.; Li, Y.; Jiao, J.; Qi, X. Eur. J. Org. Chem. 2007, 36, 6084.
  24. Xu, Z. L.; Li, H. X.; Ren, Z. G.; Du, W. Y.; Xu, W. C.; Lang, J. P. Tetrahedron 2011, 67, 5282. https://doi.org/10.1016/j.tet.2011.05.025
  25. Chen, J. L.; Song, G. Y.; Pan, C. L.; Li, X. W. Org. Lett. 2012, 12, 5426.
  26. Horie, H.; Koyama, I.; Kurahashi, T.; Matsubara, S. Chem. Commun. 2011, 47, 2658. https://doi.org/10.1039/c0cc04061d
  27. Iglesias, M. J.; Prieto, A.; Nicasio, M. C. Adv. Synth. Catal. 2010, 352, 1949. https://doi.org/10.1002/adsc.201000223
  28. Levy, A. A.; Rains, H. C.; Smiles, S. I. J. Chem. Soc. 1931, 3264. https://doi.org/10.1039/jr9310003264
  29. Xiang, J. B.; Zhu, T.; Dang, Q.; Bai, X. J. Org. Chem. 2010, 75, 8147. https://doi.org/10.1021/jo101798p
  30. Yang, H.; Li, Z. B.; Shin, D. S.; Wang, L. Y.; Zhou, J. Z.; Qiao, H. B.; Tian, X.; Ma, X. Y.; Zuo, H. Synlett 2010, 3, 483.
  31. Tian, X.; Wu, R. M.; Liu, G.; Li, Z. B.; Wei, H. L.; Yang, H.; Shin, D. S.; Wang, L. Y.; Zuo, H. ARKIVOC 2011, 10, 118.
  32. Tsaranova, T. V. Khim. Geterotsikl. Soedin. 1965, 6, 909.
  33. Wang, H. G.; Wang, Y.; Peng, C. L.; Zhang, J. C.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217. https://doi.org/10.1021/ja1067993

Cited by

  1. ChemInform Abstract: Synthesis of N-Azaaryl Anilines: An Efficient Protocol via Smiles Rearrangement. vol.44, pp.40, 2013, https://doi.org/10.1002/chin.201340160
  2. -Terarylphosphine Catalyst vol.82, pp.5, 2017, https://doi.org/10.1002/cplu.201700042
  3. A Facial Protocol for the Synthesis of Benzofuran Derivatives by the Reaction of o-Hydroxy Aryl Ketone, Amine and Chloroacetyl Chloride vol.35, pp.6, 2014, https://doi.org/10.5012/bkcs.2014.35.6.1743
  4. Sterically enriched bulky 1,3-bis(N,N′-aralkyl)benzimidazolium based Pd-PEPPSI complexes for Buchwald-Hartwig amination reactions vol.44, pp.27, 2020, https://doi.org/10.1039/d0nj01294g