Iodine-induced regioselective C-C and C-N bonds formation of N -protected indoles

Journal of Organic Chemistry

Volumn 76, Issue 2, 2011, Pages 744-747

  Li, Ying Xiu ^a   Ji, Ke Gong ^a   Wang, Hai Xi ^a   Ali, Shaukat ^a   Liang, Yong Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON-RICH; GOOD YIELD; INDOLE DERIVATIVES; MORPHOLINES; REGIO-SELECTIVE;

INDUSTRIAL CHEMICALS; IODINE;

REGIOSELECTIVITY;

2,3' BIINDOLE DERIVATIVE; 4 (1H INDOL 2 YL) MORPHOLINE; CARBON; INDOLE DERIVATIVE; IODINE; MORPHOLINE DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; SYNTHESIS;

INDOLES; IODINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MORPHOLINES; STEREOISOMERISM;

EID: 78651519029     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1023014     Document Type: Article

References (50)

1. Baeyer, A. Justus Liebigs Ann. Chem. 1866, 140, 295.
2. For historical overviews of indole chemistry, see: Julian, P. L.; Meyer, E. W.; Printy, H. C. in Heterocyclic Compounds; Elderfield, R. C, Ed.; Wiley: New York, 1952; Vol. 3, pp 1 -274.
3. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
4. Sundberg, R. J. Indoles; Academic Press:, London, UK, 1996.
5. Brancale, A.; Silvestri, R. Med. Res. Rev. 2007, 27, 209
6. Usami, Y.; Yamaguchi, J.; Numata, A. Heterocycles. 2004, 63, 1123
7. Wang, H.-J.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Nat. Prod. 1998, 61, 804
8. Varoglu, M.; Corbett, T. H.; Valeriote, F. A.; Crews, P. J. Org. Chem. 1997, 62, 7078
9. Springer, J. P.; Buchi, G.; Kobbe, B.; Demain, A. L.; Clardy, J. Tetrahedron Lett. 1977, 18, 2403
10. Barrow, C. J.; Cai, P.; Snyder, J. K.; Sedlock, D. M.; Sun, H. H.; Cooper, R. J. Org. Chem. 1993, 58, 6016
11. Greiner, D.; Bonaldi, T.; Eskeland, R.; Roemer, E.; Imhof, A. Nat. Chem. Biol. 2005, 1, 143
12. Zhang, Y.-X.; Chen, Y.; Guo, X.-N.; Zhang, X.-W.; Zhao, W.-M.; Zhong, L.; Zhou, J.; Xi, Y.; Lin, L.-P.; Ding, J. Anti-Cancer Drugs 2005, 16, 515
13. Koulouri, S.; Malamidou-Xenikaki, E.; Spyroudis, S. Tetrahedron 2005, 61, 10894
14. Talaz, O.; Saracoglu, N. Tetrahedron 2010, 66, 1902
15. Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Nagase, Y.; Shirakawa, E. J. Am. Chem. Soc. 2008, 130 (47) 15823
16. Gómez-Lor, B.; Echavarren, A. M. Org. Lett. 2004, 6, 2993
17. Velezheva, V. S.; Ryabova, S. Yu.; Mel'man, A. I.; Pol'shakov, V. I. Khim. Geterotsikl. Soedin. 1992, 49
18. Duong, H. A.; Chua, S.; Huleatt, P. B.; Chai, C. L. L. J. Org. Chem. 2008, 73, 9177
19. Skelton, B. W.; White, A. H. Tetrahedron Lett. 2009, 50, 2501
20. J. Org. Chem. 2007, 72, 9225.
21. Panzella, L.; Pezzella, A.; Napolitano, A.; d'Ischia, M. Org. Lett. 2007, 9, 1411
22. Cornella, J.; Lu, P.; Larrosa, I. Org. Lett. 2009, 11, 5506
23. Dyker, G.; Hildebrandt, D.; Liu, J.-H.; Merz, K. Angew. Chem., Int. Ed. 2003, 42, 4399
24. Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Nagase, Y.; Miyamura, T.; Shirakawa, E. J. Am. Chem. Soc. 2008, 130, 15823
25. Kraus, G. A; Guo, H.-T. Org. Lett. 2008, 10, 3061
26. Lin, C. I.; Selvi, S.; Fang, J.-M.; Chou, P.-T.; Lai, C.-H.; Cheng, Y.-M. J. Org. Chem. 2007, 72, 3537
27. Kraus, G. A.; Guo, H.-T J. Org. Chem. 2009, 74, 5337
28. Liang, Z.; Zhao, J.; Zhang, Y. J. Org. Chem. 2010, 75, 170
29. Li, Y.; Wang, W.-H.; Yang, S.-D.; Li, B.-J.; Feng, C.; Shi, Z.-J. Chem. Commun. 2010, 46, 4553
30. For early studies on electrophilic cyclization reaction, see: Ren, X.-F.; Turos, E. Tetrahedron Lett. 1993, 34, 1575
31. Kitamura, T.; Takachi, T.; Kawasato, H.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1 1992, 1969
32. Kitamura, T.; Kobayashi, S.; Taniguchi, H.; Hori, K. J. Am. Chem. Soc. 1991, 113, 6240
33. Ten Hoedt, R. W. M.; Van Koten, G.; Noltes, J. G. Synth. Commun. 1977, 7, 61
34. Sonoda, T.; Kawakami, M.; Ikeda, T.; Kobayashi, S.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1976, 612. For selected examples, see
35. Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377
36. Barluenga, J.; Vazque-Villa, H.; Ballesteros, A.; Gonzalez, J. M. J. Am. Chem. Soc. 2003, 125, 9028
37. Yue, D.; Della Ca, N.; Larock, R. C. Org. Lett. 2004, 6, 1581
38. Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2005, 7, 1769
39. Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 12230
40. Tang, B.-X.; Tang, D.-J.; Tang, S.; Yu, Q.-F.; Zhang, Y.-H.; Liang, Y.; Zhong, P.; Li, J.-H. Org. Lett. 2008, 10, 1063
41. Mohapatra, D. K.; Das, P. P.; Pattanayak, M. R.; Yadav, J. S. Chem.-Eur. J. 2010, 16, 2072
42. Huo, Z.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem., 2010, 75, 1266 and reference cited therein.
43. Bi, H.-P.; Guo, L.-N.; Duan, X.-H.; Gou, F.-R.; Huang, S.-H.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2007, 9, 397
44. Xie, Y.-X.; Liu, X.-Y.; Wu, L.-Y.; Han, Y.; Zhao, L.-B.; Fan, M.-J.; Liang, Y.-M. Eur. J. Org. Chem. 2008, 1013
45. Wen, S.-G.; Liu, W.-M.; Liang, Y.-M. J. Org. Chem. 2008, 73, 4342
46. Xie, Y.-X.; Yan, Z.-Y.; Qian, B.; Deng, W.-Y.; Wu, L.-Y.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2009, 5451
47. Xie, Y.-X.; Yan, Z.-Y.; Wang, D.-Z.; Wu, L.-Y.; Qian, B.; Liu, X.-Y.; Liang, Y.-M. Eur. J. Org. Chem. 2009, 2283
48. Ji, K.-G.; Zhu, H.-T.; Yang, F.; Shu, X.-Z.; Zhao, S.-C.; Shaukat, A.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2010, 16, 1615
49. Ji, K.-G.; Zhu, H.-T.; Yang, F.; Shaukat, A.; Xia, X.-F.; Yang, Y.-F.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2010, 75, 5670
50. Berlin, A.; Canavesi, A Tetrahedron 1996, 52, 7947