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Synthesis of N-Substituted-2-Aminothiazolo[4,5-b]pyrazines by Tandem Reaction of o-Aminohalopyrazines with Isothiocyanates

  • Kwak, Se Hun (Department of Chemistry, Dongguk-University-Seoul) ;
  • Lee, Gee-Hyung (Department of Chemistry, Dongguk-University-Seoul) ;
  • Gong, Young-Dae (Department of Chemistry, Dongguk-University-Seoul)
  • Received : 2012.10.07
  • Accepted : 2012.10.21
  • Published : 2012.12.20

Abstract

Keywords

References

  1. Caleta, I.; Kralj, M.; Marjanovic, M.; Bertosa, B.; Tomic, S.; Pavlovi , G.; Paveliæ, K.; Karminski-Zamola, G. J. Med. Chem. 2009, 52, 1744. https://doi.org/10.1021/jm801566q
  2. Amnerkar, N. D.; Bhusari, K. P. Eur. J. Med. Chem. 2010, 45, 149.
  3. Kamal, A.; Srikanth, Y. V. V.; Naseer Ahmed Khan, M.; Ashraf, M.; Kashi Reddy, M.; Sultana, F.; Kaur, T.; Chashoo, G.; Suri, N.; Sehar, I.; Wani, Z. A.; Saxena, A.; Sharma, P. R.; Bhushan, S.; Mondhe, D. M.; Saxena, A. K. Bioorg. Med. Chem. 2011, 19, 7136. https://doi.org/10.1016/j.bmc.2011.09.060
  4. D'Angelo, N. D.; Kim, T.-S.; Andrews, K.; Booker, S. K.; Caenepeel, S.; Chen, K.; D'Amico, D.; Freeman, D.; Jiang, J.; Liu, L.; McCarter, J. D.; San Miguel, T.; Mullady, E. L.; Schrag, M.; Subramanian, R.; Tang, J.; Wahl, R. C.; Wang, L.; Whittington, D. A.; Wu, T.; Xi, N.; Xu, Y.; Yakowec, P.; Yang, K.; Zalameda, L. P.; Zhang, N.; Hughes, P.; Norman, M. H. J. Med. Chem. 2011, 54, 1789. https://doi.org/10.1021/jm1014605
  5. Kumbhare, R. M.; Dadmal, T.; Kosurkar, U.; Sridhar, V.; Rao, J. V. Bioorg. Med. Chem. Lett. 2012, 22, 453. https://doi.org/10.1016/j.bmcl.2011.10.106
  6. Bebernitz, G. R.; Beaulieu, V.; Dale, B. A; Deacon, R.; Duttaroy, A.; Gao, J.; Grondine, M. S.; Gupta, R. C.; Kakmak, M.; Kavana, M.; Kirman, L. C.; Liang, J.; Maniara, W. M.; Munshi, S.; Nadkarni, S. S.; Schuster, H. F.; Stams, T.; St Denny, I.; Taslimi, P. M.; Vash, B.; Caplan, S. L. J. Med. Chem. 2009, 52, 6142. https://doi.org/10.1021/jm900839k
  7. Okaniwa, M.; Hirose, M.; Imada, T.; Ohashi, T.; Hayashi, Y.; Miyazaki, T.; Arita, T.; Yabuki, M.; Kakoi, K.; Kato, J.; Takagi, T.; Kawamoto, T.; Yao, S.; Sumita, A.; Tsutsumi, S.; Tottori, T.; Oki, H.; Sang, B.-C.; Yano, J.; Aertgeerts, K.; Yoshida, S.; Ishikawa, T. J. Med. Chem. 2012, 55, 3452. https://doi.org/10.1021/jm300126x
  8. Lebsack, A. D.; Branstetter, B. J.; Hack, M. D.; Xiao, W.; Peterson, M. L.; Nasser, N.; Maher, M. P.; Ao, H.; Bhattacharya, A.; Kansagara, M.; Scott, B. P.; Luo, L.; Rynberg, R.; Rizzolio, M.; Chaplan, S. R.; Wickenden, A. D.; Guy Breitenbucher, J. Bioorg. Med. Chem. Lett. 2009, 19, 40. https://doi.org/10.1016/j.bmcl.2008.11.024
  9. Lin, R.; Johnson, S. G.; Connolly, P. J.; Wetter, S. K.; Binnun, E.; Hughes, T. V.; Murray, W. V.; Pandey, N. B.; Moreno-Mazza, S. J.; Adams, M.; Fuentes- Pesquera, A. R.; Middleton, S. A. Bioorg. Med. Chem. Lett. 2009, 19, 2333. https://doi.org/10.1016/j.bmcl.2009.02.067
  10. Jang, M. Y.; De Jonghe, S.; Segers, K.; Anne, J.; Herdewijn, P. Bioorg. Med. Chem. 2011, 19, 702. https://doi.org/10.1016/j.bmc.2010.10.027
  11. Ramtohul, Y. K.; Powell, D.; Leclerc, J.-P.; Leger, S.; Oballa, R.; Black, C.; Isabel, E.; Li, C. S.; Crane, S.; Robichaud, J.; Guay, J.; Guiral, S.; Zhang, L.; Huang, Z. Bioorg. Med. Chem. Lett. 2011, 21, 5692. https://doi.org/10.1016/j.bmcl.2011.08.037
  12. Liu, J.; Patch, R. J.; Schubert, C.; Player, M. R. J. Org. Chem. 2005, 70, 10194. https://doi.org/10.1021/jo0517702
  13. Bakavoli, M.; Nikpour, M.; Rahimizadeh, M. J. Heterocyclic Chem. 2006, 43, 1327. https://doi.org/10.1002/jhet.5570430527
  14. Wada, A.; Yamamoto, J.; Kanatomo, S. Hetrocycles 1987, 26, 585. https://doi.org/10.3987/R-1987-03-0585
  15. Choi, H. G.; Sim, T.; Gray, N.; Zhou, W.; Chang, J. W.; Zhang, J.; Weisberg, E. WO2010144909, 2010; Reaxys Rx-ID: 30101909.
  16. Masuda, K.; Kida, S.; Hayashi, K.; Katou, M.; Yoshikawa, N.; Kugimiya, A.; Nakajima, M.; Tanaka, N. WO201044441, 2010; Reaxys Rx-ID: 3397914.
  17. Joyce, L. L.; Evindar, G.; Batey, R. A. Chem. Commun. 2004, 446.
  18. Feng, E.; Huang, H.; Zhou, Y.; Ye, D.; Jiang, H.; Liu, H. J. Comb. Chem. 2010, 12, 422. https://doi.org/10.1021/cc9001839
  19. Saha, P.; Ramana, T.; Purkait, N.; Ali, M. A.; Paul, R.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 8719. https://doi.org/10.1021/jo901813g
  20. Shen, G.; Lv, X.; Bao, W. Eur. J. Org. Chem. 2009, 5897.
  21. Ding, Q.; Cao, B.; Liu, X.; Zong, Z.; Peng, Y.-Y. Green Chem. 2010, 12, 1607. https://doi.org/10.1039/c0gc00123f
  22. Guo, Y.-J.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Tetrahedron Lett. 2010, 51, 649. https://doi.org/10.1016/j.tetlet.2009.11.086
  23. Yang, J.; Li, P.; Wang, L. Tetrahedron 2011, 67, 5543. https://doi.org/10.1016/j.tet.2011.05.121
  24. Xiao, R.; Hao, W.; Ai, J.; Cai, M. Z. J. Organomet. Chem. 2012, 705, 44. https://doi.org/10.1016/j.jorganchem.2012.01.014
  25. Ma, D.; Lu, X.; Shi, L.; Zhang, H.; Jiang, Y.; Liu, X. Angew. Chem. Int. Ed. 2011, 50, 1118. https://doi.org/10.1002/anie.201005787
  26. Verma, S. K.; Acharya, B. N.; Kaushik, M. P. Org. Biomol. Chem. 2011, 9, 1324. https://doi.org/10.1039/c0ob00859a
  27. Zhao, H.; Wang, M.; Su, W.; Hong, M. Adv. Synth. Catal. 2010, 352, 1301. https://doi.org/10.1002/adsc.200900856

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