Iodine-catalyzed efficient synthesis of azaarene substituted 3-hydroxy-2-oxindole derivatives through sp 3 C-H functionalization

Tetrahedron

Volumn 68, Issue 39, 2012, Pages 8286-8292

  Vuppalapati, Srinivasu V N ^a   Lee, Yong Rok ^a  

^a Yeungnam University   (South Korea)

Author keywords

3 Hydroxy 2 oxindoles; Iodine; Sp 3 C H functionalization

Indexed keywords

3 HYDROXY 1 METHYL 3 (PYRIDIN 2 YLMETHYL)INDOLIN 2 ONE; 3 HYDROXY 1 METHYL 3 (PYRIDIN 4 YLMETHYL)INDOLIN 2 ONE; 3 HYDROXY 1 METHYL 3 [(3 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; 3 HYDROXY 1 METHYL 3 [(6 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; 3 HYDROXY 1 PHENYL 3 (PYRIDIN 2 YLMETHYL)INDOLIN 2 ONE; 3 HYDROXY 3 [(3 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; 3 HYDROXY 3 [(6 METHYLPYRIDIN 2 YL)METHYL] 1 PHENYLINDOLIN 2 ONE; 3 HYDROXY 3 [(6 METHYLPYRIDIN 2 YL)METHYL] 5 NITROINDOLIN 2 ONE; 3 HYDROXY 5 METHYL 3 (PYRIDIN 2 YLMETHYL)INDOLIN 2 ONE; 3 HYDROXY 5 METHYL 3 [(6 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; 3 HYDROXY 5 NITRO 3 (PYRIDIN 2 YLMETHYL)INDOLIN 2 ONE; 5 BROMO 3 HYDROXY 3 (PYRIDIN 2 YLMETHYL)INDOLIN 2 ONE; 5 BROMO 3 HYDROXY 3 (PYRIDIN 4 YLMETHYL)INDOLIN 2 ONE; 5 BROMO 3 HYDROXY 3 [(3 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; 5 BROMO 3 HYDROXY 3 [(6 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; 5 CHLORO 3 HYDROXY 3 [(6 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; 7 BROMO 3 HYDROXY 3 [(6 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; 7 CHLORO 3 HYDROXY 3 [(6 METHYLPYRIDIN 2 YL)METHYL]INDOLIN 2 ONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTINEOPLASTIC AGENT; BENZYL DERIVATIVE; CARBON; HYDROGEN; IODINE; ISATIN DERIVATIVE; PICOLINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84865075151     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.07.051     Document Type: Article

References (43)

1. Recent reviews: V. Ritleng, C. Sirlin, and M. Pfeffer Chem. Rev. 102 2002 1731
2. F. Kakiuchi, and N. Chatani Adv. Synth. Catal. 345 2003 1077
3. M. Tobisu, and N. Chatani Angew. Chem., Int. Ed. 45 2006 1683
4. K.R. Campos Chem. Soc. Rev. 36 2007 1069
5. M. Rueping, and N. Tolstoluzhsky Org. Lett. 13 2011 1095
6. B. Qian, P. Xie, Y. Xie, and H. Huang Org. Lett. 13 2011 2580
7. H. Komai, T. Yoshino, S. Matsunaga, and M. Kanai Org. Lett. 13 2011 1706
8. K.A. Ubaidullaev, R. Shakirov, and S.Y. Yunosov Khim. Prir. Soedin. 12 1976 553
9. K. Monde, K. Sasaki, A. Shirata, and M. Takasugi Phytochemistry 30 1991 2915
10. Y. Kamano, H.-P. Zhang, Y. Ichihara, H. Kizu, K. Komiyama, and G.R. Pettit Tetrahedron Lett. 36 1995 2783
11. H.-P. Zhang, Y. Kamano, Y. Ichihara, H. Kizu, K. Komiyama, H. Itokawa, and G.R. Pettit Tetrahedron 51 1995 5523
12. Y. Koguchi, J. Kohno, M. Nishio, K. Takahashi, T. Okuda, T. Ohnuki, and S. Komatsubara J. Antibiot. 53 2000 105
13. H. Kobayashi, S.Y. Kazuo, K. Furihata, K. Nagai, K.I. Suzuki, Y. Hayakawa, H. Seto, B.S. Yun, I.J. Ryoo, J.S. Kim, C.J. Kim, and I.D. Yoo J. Antibiot. 54 2001 1019
14. H. Kobayashi, Y.K. Shin, K. Furihata, K. Nagai, K.I. Suzuki, Y. Hayakawa, H. Seto, B.S. Yun, I.J. Ryoo, J.S. Kim, C.J. Kim, and I.D. Yoo J. Antibiot. 54 2001 1013
15. H. Suzuki, H. Morita, M. Shiro, and J. Kobayashi Tetrahedron 60 2004 2489
16. G.D. Henry Tetrahedron 60 2004 6043
17. J.P. Michael Nat. Prod. Rep. 22 2005 627
18. T. Laird Org. Process Res. Dev. 10 2006 851
19. L.-C. Campeau, and K. Fagnou Chem. Soc. Rev. 36 2007 1058
20. M.C. Bagley, C. Glover, and E.A. Merritt Synlett 2007 2459
21. C. Marti, and E.M. Carreira Eur. J. Org. Chem. 2003 2209
22. A.B. Dounay, and L.E. Overman Chem. Rev. 103 2003 2945
23. H. Lin, and S.J. Danishefsky Angew. Chem., Int. Ed. 42 2003 36
24. C.V. Galliford, and K.A. Scheidt Angew. Chem., Int. Ed. 46 2007 8748
25. P. Satyamaheshwar Curr. Bioact. Compd. 5 2009 20
26. F. Zhou, Y.L. Liu, and J. Zhou Adv. Synth. Catal. 352 2010 1381
27. H.B. Rasmussen, and J.K. MacLeod J. Nat. Prod. 60 1997 1152
28. S.J. Garden, J.C. Torres, A.A. Ferreira, R.B. Silva, and A.C. Pinto Tetrahedron Lett. 38 1997 1501
29. S. Miah, C.J. Moody, I.C. Richards, and A.M.Z. Slawin J. Chem. Soc., Perkin Trans. 1 1997 2405
30. G.K. Jnaneshwara, A.V. Bedekar, and V.H. Deshpande Synth. Commun. 29 1999 3627
31. G.K. Jnaneshwar, and V.H. Deshpande J. Chem. Res., Synop. 1999 632
32. M. Suchy, P. Kutschy, K. Monde, H. Goto, N. Harada, M. Takasugi, M. Dzurilla, and E. Balentova J. Org. Chem. 66 2001 3940
33. T. Tokunaga, W.E. Hume, T. Umezome, K. Okazaki, Y. Ueki, K. Kumagai, S. Hourai, J. Nagamine, H. Seki, M. Taiji, H. Noguchi, and R. Nagata J. Med. Chem. 44 2001 4641
34. R. Niu, J. Xiao, T. Liang, and X. Li Org. Lett. 14 2012 676
35. J.S. Yadav, B.V.S. Reddy, M.S. Reddy, and A.R. Prasad Tetrahedron Lett. 43 2002 9703
36. R. Saeeng, U. Sirion, P. Sahakitpichan, and M. Isobe Tetrahedron Lett. 44 2003 6211
37. N. Mori, and H. Togo Synlett 2004 880
38. L. Royer, S.K. De, and R.A. Gibbs Tetrahedron Lett. 46 2005 4595
39. B.K. Banik, M. Fernandez, and C. Alvarez Tetrahedron Lett. 46 2005 2479
40. H. Togo, and S. Iida Synlett 2006 2159
41. M. Jereb, D. Vrazic, and M. Zupan Tetrahedron 67 2011 1355
42. A. Kumar, G. Gupta, and S. Srivastava Org. Lett. 13 2011 6366
43. E.M. Karlsen, and J. Spanget-Larsen Chem. Phys. Lett. 473 2009 227