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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 9
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Original Articles

Catalyst-free benzylic C(sp3)-H functionalization of methyl quinolines with tryptanthrins

Zhu ZhengKey Laboratory for Information System of Mountainous Areas and Protection of Ecological Environment of Guizhou Province, Guizhou Normal University, Guiyang, P. R. China
,
Quanquan WuCollege of Chemistry and Materials Science, Wenzhou University, Wenzhou, P. R. China
,
Chong-Xing LiuCollege of Chemistry and Materials Science, Wenzhou University, Wenzhou, P. R. China
,
Zhannan YangKey Laboratory for Information System of Mountainous Areas and Protection of Ecological Environment of Guizhou Province, Guizhou Normal University, Guiyang, P. R. ChinaCorrespondence[email protected]
&
Hongxin LiuCollege of Chemistry and Materials Science, Wenzhou University, Wenzhou, P. R. ChinaCorrespondence[email protected]
Pages 1092-1098 | Received 21 Aug 2017, Published online: 09 Apr 2018

References

  • (a) Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2006, 45, 1683–1684; (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077–1101; (c) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174–238; (d) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094–5115; (e) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677–685; (f) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293–1314.
  • (a) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935–10941; (b) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154–13155; (c) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634–12635; (d) Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759–1762; (e) Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965–3972.
  • (a) Campeau, L.-C.; Schipper, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266–3267; (b) Schipper, D. J.; Campeau, L.-C.; Fagnou, K. Tetrahedron. 2009, 65, 3155–3164; (c) Mousseau, J. J.; Lariv-ee, A.; Charette, A. B. Org. Lett. 2008, 10, 1641–1643; (d) Burton, P. M.; Morris, J. A. Org. Lett. 2010, 12, 5359–5361; (e) Jiang, H.; Chen, H.; Wang, A.; Liu, X. Chem. Commun. 2010, 46, 7259–7261; (f) Tsurugi, H.; Yamamoto, K.; Mashima, K. J. Am. Chem. Soc. 2011, 133, 732–735; (g) Song, G. Y.; Su, Y.; Gong, X.; Han, K. L.; Li, X. W. Org. Lett. 2011, 13, 1968–1971.
  • (a) Houghton, P. J.; Woldemariam, T. Z.; Watanabe, T.; Yates, M. Planta Med. 1999, 65, 250–254; (b) Michael, J. P. Nat. Prod. Rep. 2000, 17, 603–620; (c) Jacquemond-Collet, I.; Benoit-Vical, F.; Valentin, M. A.; Stanislas, E.; Mallie, M.; Fouraste, I. Planta Med. 2002, 68, 68–69.
  • (a) Burton, P. M.; Morris, J. A. Org. Lett. 2010, 12, 5359–5361; (b) Qian, B.; Guo, S.; Shao, J.; Zhu, Q.; Yang, L.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2010, 132, 3650–3651; (c) Shang, R.; Yang, Z. W.; Wang, Y.; Zhang, S. L.; Liu, L. J. Am. Chem. Soc. 2010, 132, 14391–14393; (d) Jin, J. J.; Niu, H. Y.; Qu, G. R.; Guo, H. M.; Fossey, J. S. RSC Adv. 2012, 2, 5968–5971; (e) Yang, Y.; Xie, C.; Xie, Y.; Zhang, Y. Org. Lett. 2012, 14, 957–959; (f) Obora, Y.; Ogawa, S.; Yamamoto, N. J. Org. Chem. 2012, 77, 9429–9433; (g) Qian, B.; Xie, P.; Xie, Y.; Huang, H. Org. Lett. 2011, 13, 2580–2583; (h) Liu, J. Y.; Niu, H. Y.; Wu, S.; Qu, G. R.; Guo, H. M. Chem. Commun. 2012, 48, 9723–9725.
  • (a) Rueping, M.; Tolstoluzhsky, N. Org. Lett. 2011, 13, 1095–1097; (b) Komai, H.; Yoshino, T.; Matsunaga, S.; Kanai, M. Org. Lett. 2011, 13, 1706–1707; (c) Srinivasu, V. N. V.; Yong, R. L. Tetrahedron 2012, 68, 8286.
  • (a) Niu, R.; Xiao, J.; Liang, T.; Li, X. Org. Lett. 2012, 14, 676–679; (b) Wang, F. F.; Luo, C. P.; Wang, Y.; Deng, G.; Yang, L. Org. Biomol. Chem. 2012, 10, 8605–8608.
  • Atul, K.; Ratnakar, D. S. Green Chem. 2015, 17, 848–851.
  • (a) Niu, R.; Xiao, J.; Liang, T.; Li, X. Chin. J. Catal. 2012, 33, 1636–1641; (b) Graves, V. B.; Shaikh, A. Tetrahedron Lett. 2013, 54, 695–698.
  • (a) Tipson, R. S. J. Am. Chem. Soc. 1945, 67, 507–511; (b) Pi, D.; Jiang, K.; Zhou, H.; Sui, Y.; Uozumi, Y.; Zou, K. RSC Adv. 2014, 4, 57875–57884; (c) Jin, J. J.; Niu, H. Y.; Qu, G. R.; Guo, H. M.; Fossey, J. S. RSC Adv. 2012, 2, 5968–5971; (d) Graves, V. B.; Shaikh, A. Tetrahedron Lett. 2013, 54, 695–698; (e) Vuppalapati, S. V. N.; Lee, Y. R. Tetrahedron 2012, 68, 8286–8292; (f) Niu, R.; Yang, S.; Xiao, J.; Liang, T.; Li, X. Chin. J. Catal. 2012, 33, 1636–1641; (g) Niu, R.; Xiao, J.; Liang, T.; Li, X. W. Org. Lett. 2012, 14, 676–679; (h) Jian, J. J.; Wang, D. C.; Niu, H. Y.; Wu, S.; Qu, G. R.; Zhang, Z. B.; Guo, H. M. Tetrahedron 2013, 69, 6579–6584; (i) Wang, F. F.; Luo, C. P.; Wang, Y.; Deng, G. J.; Yang, L. Org. Biolmol. Chem. 2012, 10, 8605–8608.
  • (a) Rueping, M.; Tolstoluzhsky, N. Org. Lett. 2011, 13, 1095–1097; (b) Qian, B.; Guo, S.; Shao, J.; Zhu, Q.; Yang, L.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2010, 132, 3650–3651; (c) Qian, B.; Guo, S.; Xia, C.; Huang, H. Adv. Synth. Catal. 2010, 352, 3195–3200; (d) Qian, B.; Xie, P.; Xie, Y.; Huang, H. Org. Lett. 2011, 13, 2580–2583.
  • Nageswara Rao, N.; Meshram, H. M. Tetrahedron Lett. 2013, 54, 1315–1317.
  • (a) Qian, B.; Yang, L.; Huang, H. M. Tetrahedron Lett. 2013, 54, 711–714; (b) Komai, H.; Yoshino, T.; Matsunaga, S.; Kanai, M. Org. Lett. 2011, 13, 1706–1709; (c) Liu, J. Y.; Niu, H. Y.; Wu, S.; Qu, G. R.; Guo, H. M. Chem. Commun. 2012, 48, 9723–9725.
  • (a) Xu, L. B.; Shao, Z. Z.; Wang, L.; Xiao, J. Org. Lett. 2014, 16, 796–799; (b) Yan, Y. Z.; Xu, K.; Fang, Y.; Wang, Z. Y. J. Org. Chem. 2011, 76, 6849–6855; (c) Xu, L. B.; Shao, Z. Z.; Wang, L.; Zhao, H. L.; Xiao, J. Tetrahedron Lett. 2014, 55, 6856–6860; (d) Nageswara Rao, N.; Meshram, H. M. Tetrahedron Lett. 2013, 54, 5087–5090; (e) Raghu, M.; Rajasekhar, M.; Chandra, O. R. B.; Suresh, R. C.; Subba Reddy, B. V. Tetrahedron Lett. 2013, 54, 3503–3506.
  • (a) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881–7882; (b) Krivogorsky, A. B.; Nelson, K. C.; Douglas, A.; Grundt, P. Bioorg. Med. Chem. Lett. 2013, 23, 1032–1035; (c) Jao, C. W.; Lin, W. C.; Wu, Y. T.; Wu, P. L. J. Nat. Prod. 2008, 71, 1275–1279; (d) Nolan, K. A.; Timson, D. J.; Stratforda, I. J.; Bryce, R. A. Bioorg. Med. Chem. Lett. 2006, 16, 6246–6254; (e) Yang, S.; Li, X.; Hu, F.; Li, Y.; Yang, Y.; Yan, J. Med. Chem. 2013, 56, 8321–8331.
  • (a) Kang, G. W.; Luo, Z. L.; Liu, C. X.; Gao, H.; Wu, Q. Q.; Wu, H. Y.; Jiang, J. Org. Lett. 2013, 15, 4738–4741; (b) Gao, H.; Luo, Z. L.; Ge, P. J.; He, J. Q.; Zhou, F.; Zhen, P. P.; Jiang, J. Org. Lett. 2015, 17, 5962–5965; (c) Vaidya, S. D.; Argade, N. P. Org. Lett. 2013, 15, 4006–4009; (d) Gahtory, M. D.; Chouhan, R.; Sharma, V.; Nair, A. Org. Lett. 2013, 15, 3942–3945; (e) Chen, L.; Yin, X. P.; Wang, C.; Zhou, H. J. Org. Biomol. Chem. 2014, 12, 6033–6048; (f) Liao, F. M.; Liu, Y. L.; Yu, J. S.; Feng Zhou, F.; Zhou, J. Org. Biomol. Chem. 2015, 13, 8906–8911.
  • Jamala, Z.; Teo, Y.-C. RSC. Adv. 2015, 5, 9–26953.

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