Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation

Tetrahedron

Volumn 62, Issue 7, 2006, Pages 1527-1535

  Wang, Shun Yi ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

3,3 Di(heteroaryl)indolin 2 one; CAN; Indole; Isatin

Indexed keywords

1 METHYL 3,3 BIS(1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (1H INDOL 3 YL) 1 METHYL 3 (3 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (1H INDOL 3 YL) 3 (1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (1H INDOL 3 YL) 3 (3 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (1H INDOL 3 YL) 3 (5 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (1H INDOL 3 YL) 3 (6 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (1H INDOL 3 YL) 3 (7 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (3 METHYL 1H INDOL 2 YL) 3 (1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (3 METHYL 1H INDOL 2 YL) 3 (5 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 (3 METHYL 1H INDOL 2 YL) 3 (7 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3 HYDROXY 3 INDOLYLINDOLIN 2 ONE; 3,3 BIS(1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 BIS(5 (BENZYLOXY) 1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 BIS(5 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 BIS(5 NITRO 1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 BIS(6 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 BIS(7 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 DI(1H INDOL 3 YL) 1 METHYLINDOLIN 2 ONE; 3,3 DI(1H INDOL 3 YL)INDOLIN 2 ONE; 3,3 DI(INDOLYL)INDOLIN 2 ONE; 4 BROMO 3,3 BIS(1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 4 BROMO 3,3 DI(1H INDOL 3 YL)INDOLIN 2 ONE; 6 BROMO 3 (1H INDOL 3 YL) 3 (3 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 6 BROMO 3,3 BIS(1 METHYL 1H INDOL 3 YL)INDOLIN 2 ONE; 6 BROMO 3,3 DI(1H INDOL 3 YL)INDOLIN 2 ONE; AMMONIUM NITRATE; CERIC AMMONIUM NITRATE; CERIUM; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; ULTRASOUND;

EID: 30744466643     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.011     Document Type: Article

References (37)

1. R.J. Sundberg The Chemistry of Indoles 1996 Academic New York
2. M.H. Hubacher, S. Doernberg, and A. Horner J. Am. Pharm. Assoc. 42 1953 23 30
3. A. Gazit, N. Osherov, I. Posner, P. Yaish, E. Poradosu, C. Gilon, and A. Levitzki J. Med. Chem. 34 1991 1896 1907
4. S. Dilber, M. Saban, J. Jelaca, A. Gelineo, L. Arsenijevic, and M. Bogavac Pharmazie 44 1989 649 650
5. D.A. Klumpp, K.Y. Yeung, G.K.S. Prakash, and G.A. Olah J. Org. Chem. 63 1998 4481 4484
6. K.C. Joshi, V.N. Pathak, and S.K. Jain Pharmazie 35 1980 677 679
7. V.V. Bolotov, V.V. Drugovina, L.V. Yakovleva, and A.I. Bereznyakova Khim.-Farm. Zh. 16 1982 58 61
8. (c) William, C.E. US Patent 3,558,653, 1971.
9. H. Pajouhesh, R. Parsons, and F.D. Popp J. Pharm. Sci. 72 1983 318 321
10. F. Garrido, J. Ibanez, E. Gonalons, and A. Giraldez Eur. J. Med. Chem. 10 1975 143 149
11. A. Natarajan, Y.-H. Fan, H. Chen, Y. Guo, J. Iyasere, F. Harbinski, W.J. Christ, H. Aktas, and J.A. Halperin J. Med. Chem. 47 2004 1882 1885
12. J. Bergman, and N. Eklund Tetrahadron 36 1980 1445 1450
13. J. Azizian, A.A. Mohammadi, A.R. Karimi, and M.R. Mohammadizadeh J. Chem. Res. Synop. 6 2004 424 426
14. P. Hewawasam, V.K. Gribkoff, Y. Pendri, S.I. Dworetzky, N.a. Meanwell, E. Martinez, C.G. Boissard, D.J. Post-Munson, J.T. Trojnacki, K. Yeleswaram, L.M. Pajor, J. Knipe, Q. Gao, R. Perrone, and J.E. Starrett Jr. Bioorg. Med. Chem. Lett. 12 2002 1023 1026
15. K.C. Nicolaou, M. Bella, D.Y.-K. Chen, X. Huang, T. Ling, and S.A. Snyder Angew. Chem., Int. Ed. 41 2002 3495 3499
16. A.A. Klumpp, K.Y. Yeung, G.K. Surya Prakash, and G.A. Olah J. Org. Chem. 63 1998 4481 4484
17. M. Kobayashi, S. Aoki, K. Gato, K. Matsunami, M. Kurosu, and I. Kitagawa Chem. Pharm. Bull. 42 1994 2449 2451
18. For reviews on CAN mediated reactions see: (a) J.R. Hwu, and K.Y. King Curr. Sci. 81 2001 1043 1053
19. G.A. Molander Chem. Rev. 92 1992 29 89
20. T.L. Ho Organic Synthesis by Oxidation with Metal Compounds 1986 Plenum New York and references cited therein
21. T. Imamoto Lanthanide Reagents in Organic Synthesis 1994 Academic London 119
22. V. Nair, J. Mathew, and J. Prabhakaran Chem. Soc. Rev. 1997 127 144
23. For examples, see: (a) V. Nair, S.B. Panicker, L.G. Nair, T.G. George, and A. Augustine Synlett 2003 156 160
24. E. Baciocchi, and R. Ruzziconi Synth. Commun. 18 1988 1841 1851
25. E. Baciocchi, and R. Ruzziconi J. Org. Chem. 51 1986 1645 1651
26. E. Baciocchi, and R. Ruzziconi Gazz. Chim. Ital. 116 1986 671 678
27. C.N. Ramesh, and B.D. Ravindranath J. Chem. Res. (S) 2003 72 74
28. X.-F. Zeng, S.-J. Ji, and S.-Y. Wang Tetrahedron 61 2005 10235 10241
29. S.-J. Ji, S.-Y. Wang, Y. Zhang, and T.-P. Loh Tetrahedron 60 2004 2051 2056
30. S.-J. Ji, M.-F. Zhou, D.G. Gu, S.-Y. Wang, and T.-P. Loh Synlett 2003 2077 2079
31. S.-J. Ji, M.-F. Zhou, D.G. Gu, Z.Q. Jiang, and T.-P. Loh Eur. J. Org. Chem. 2004 1584 1587
32. D.-G. Gu, S.-J. Ji, Z.-Q. Jiang, M.-F. Zhou, and T.-P. Loh Synlett 2005 959 963
33. S.-J. Ji, and S.-Y. Wang Synlett 2003 2074 2076
34. S.-Y. Wang, S.-J. Ji, and T.-P. Loh Synlett 2003 2377 2379
35. -1.
36. U. Berens, J.M. Brown, J. Long, and R. Selke Tetrahedron: Asymmetry 7 1996 285 292
37. The migration of groups from the 3- to the 2-position of indole has been observed in the alkylation of 3-substituted indoles. see: A.H. Jackson, B. Naidoo, and P. Smith Tetrahedron 24 1968 6119 6129