Synthesis of lactams by isomerization of oxindoles substituted at C-3 by an ω-amino chain

Journal of Organic Chemistry

Volumn 79, Issue 22, 2014, Pages 10945-10955

  Sarraf, Daad ^a   Richy, Nicolas ^a   Vidal, Joëlle ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; ISOMERIZATION; ISOMERS;

ASYMMETRIC CARBONS; ASYMMETRIC SYNTHESIS; ELECTRON WITHDRAWING GROUP; OXINDOLES;

AMIDES;

CARBON; LACTAM DERIVATIVE; NITRO DERIVATIVE; OMEGA AMINO ACID; ANILINE DERIVATIVE; INDOLE DERIVATIVE; LACTAM; OXINDOLE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; ELECTRON; ISOMERIZATION; CATALYSIS; CHEMISTRY; SYNTHESIS;

ANILINE COMPOUNDS; CATALYSIS; INDOLES; LACTAMS; MOLECULAR STRUCTURE;

EID: 84913582685     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501978j     Document Type: Article

References (72)

1. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
2. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
3. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003
4. Millemaggi, A.; Taylor, R. J. K. Eur. J. Org. Chem. 2010, 4527
5. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
6. Klein, J. E. M. N.; Taylor, R. J. K. Eur. J. Org. Chem. 2011, 6821
7. Ball-Jones, N. R.; Badillo, J. J.; Franz, A. K. Org. Biomol. Chem. 2012, 10, 5165
8. Kumar, A.; Chimni, S. S. RSC Adv. 2012, 2, 9748
9. Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Chem. Soc. Rev. 2012, 41, 7247
10. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104
11. Singh, G. S.; Desta, Z. Y. In Chemistry and Pharmacology of Naturally Occurring Bioactive Compounds; Brahmachari, G., Ed.; CRC Press: Boca Raton, 2013; p 73.
12. Chauhan, P.; Chimni, S. S. Tetrahedron: Asymmetry 2013, 24, 343
13. Hong, L.; Wang, R. Adv. Synth. Catal. 2013, 355, 1023
14. Mohammadi, S.; Heiran, R.; Herrera, R. P.; Marqués-López, E. ChemCatChem 2013, 5, 2131
15. Liu, Y.; Wang, H.; Wan, J. Asian J. Org. Chem. 2013, 2, 374
16. Chen, L.; Yin, X.-P.; Wang, C.-H.; Zhou, J. Org. Biomol. Chem. 2014, 12, 6033
17. Kohno, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Kuroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990
18. Genin, E.; Reboud-Ravaux, M.; Vidal, J. Curr. Top. Med. Chem. 2010, 10, 232
19. Rentsch, A.; Landsberg, D.; Brodmann, T.; Bülow, L.; Girbig, A.-K.; Kalesse, M. Angew. Chem., Int. Ed. 2013, 52, 5450
20. Desvergne, A.; Genin, E.; Maréchal, X.; Gallastegui, N.; Dufau, L.; Richy, N.; Groll, M.; Vidal, J.; Reboud-Ravaux, M. J. Med. Chem. 2013, 56, 3367
21. Groll, M.; Gallastegui, N.; Marechal, X.; Le Ravalec, V.; Basse, N.; Richy, N.; Genin, E.; Huber, R.; Moroder, L.; Vidal, J.; Reboud-Ravaux, M. ChemMedChem 2010, 5, 1701
22. Freter, K.; Weissbach, H.; Redfield, B.; Udenfriend, S.; Witkop, B. J. Am. Chem. Soc. 1958, 80, 983
23. Wenkert, E.; Bernstein, B. S.; Udelhofen, J. H. J. Am. Chem. Soc. 1958, 80, 4899
24. Islip, P. J.; White, A. C. J. Chem. Soc. 1964, 1201
25. Nakagawa, M.; Maruyama, T.; Hirakoso, K.; Hino, T. Tetrahedron Lett. 1980, 21, 4839
26. Nakagawa, M.; Kato, S.; Fukazawa, H.; Hasegawa, Y.; Miyazawa, J.; Hino, T. Tetrahedron Lett. 1985, 26, 5871
27. Shishido, K.; Shitara, E.; Komatsu, H.; Hiroya, K.; Fukumoto, K.; Kametani, T. J. Org. Chem. 1986, 51, 3007
28. Kawasaki, T.; Takamiya, W.; Okamoto, N.; Nagaoka, M.; Hirayama, T. Tetrahedron Lett. 2006, 47, 5379
29. Kim, S. C.; Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1133
30. Kim, S. C.; Gowrisankar, S.; Kim, J. N. Tetrahedron Lett. 2006, 47, 3463
31. Movassaghi, M.; Schmidt, M. A.; Ashenhurst, J. A. Org. Lett. 2008, 10, 4009
32. Wu, H.; Xue, F.; Xiao, X.; Qin, Y. J. Am. Chem. Soc. 2010, 132, 14052
33. Qiu, J.; Zhang, J.-X.; Liu, S.; Hao, X.-J. Tetrahedron Lett. 2013, 54, 300
34. For a similar isomerization leading to γ-lactones, see: Liu, Y.-L.; Wang, B.-L.; Cao, J.-J.; Chen, L.; Zhang, Y.-X.; Wang, C.; Zhou, J. J. Am. Chem. Soc. 2010, 132, 15176
35. Khuzhaev, V. U. Chem. Nat. Compd. 2004, 40, 516
36. Chen, W.-B.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2010, 66, 1441
37. Takayama, H.; Matsuda, Y.; Masubuchi, K.; Ishida, A.; Kitajima, M.; Aimi, N. Tetrahedron 2004, 60, 893
38. Inoue, M.; Sakazaki, H.; Furuyama, H.; Hirama, M. Angew. Chem., Int. Ed. 2003, 42, 2654
39. Natural Lactones and Lactams: Synthesis, Occurrence and Biological Activity; Janecki, T., Ed.; Wiley: New York, 2013.
40. Smith, M. B. In Science of Synthesis; Weinreb, S., Ed.; Georg Thieme Verlag: Stuttgart, 2005; Vol. 21, p 647.
41. Nubbemeyer, U. In Stereoselective Heterocyclic Synthesis III; Metz, P., Ed.; Topics in Current Chemistry; Springer-Verlag: Berlin, 2001; Vol. 216, p 125.
42. Ha, K.; Monbaliu, J-C. M.; Williams, B. C.; Pillai, G. G.; Ocampo, C. E.; Zeller, M.; Stevens, C. V.; Katritzky, A. R. Org. Biomol. Chem. 2012, 10, 8055
43. Sharma, A.; Appukkuttan, P.; Van der Eycken, E. Chem. Commun. 2012, 48, 1623
44. David, O.; Meester, W. J. N.; Bieräugel, H.; Schoemaker, H. E.; Hiemstra, H.; van Maarseveen, J. H. Angew. Chem., Int. Ed. 2003, 42, 4373
45. Bui, T.; Syed, S.; Barbas, C. F. J. Am. Chem. Soc. 2009, 131, 8758
46. Kato, Y.; Furutachi, M.; Chen, Z.; Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168
47. He, R.; Shirakawa, S.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 16620
48. Li, X.; Zhang, B.; Xi, Z.-G.; Luo, S.; Cheng, J.-P. Adv. Synth. Catal. 2010, 352, 416
49. Ding, M.; Zhou, F.; Qian, Z.-Q.; Zhou, J. Org. Biomol. Chem. 2010, 8, 2912
50. Ding, M.; Zhou, F.; Liu, Y.-L.; Wang, C.-H.; Zhao, X.-L.; Zhou, J. Chem. Sci. 2011, 2, 2035
51. Han, Y.-Y.; Wu, Z.-J.; Chen, W.-B.; Du, X.-L.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2011, 13, 5064
52. Liu, X.-L.; Wu, Z.-J.; Du, X.-L.; Zhang, X.-M.; Yuan, W.-C. J. Org. Chem. 2011, 76, 4008
53. Chen, X.; Zhu, W.; Qian, W.; Feng, E.; Zhou, Y.; Wang, J.; Jiang, H.; Yao, Z.-J.; Liu, H. Adv. Synth. Catal. 2012, 354, 2151
54. Wang, C.; Yang, X.; Enders, D. Chem.-Eur. J. 2012, 18, 4832
55. Yang, W.; Wang, J.; Du, D.-M. Tetrahedron: Asymmetry 2012, 23, 972
56. Retini, M.; Bergonzini, G.; Melchiorre, P. Chem. Commun. 2012, 48, 3336
57. Noole, A.; Järving, I.; Werner, F.; Lopp, M.; Malkov, A.; Kanger, T. Org. Lett. 2012, 14, 4922
58. Cui, B.-D.; Han, W.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. J. Org. Chem. 2013, 78, 8833
59. Zou, L.; Bao, X.; ma, Y.; Song, Y.; Qu, J.; Wang, B. Chem. Commun. 2014, 50, 5760
60. Shirakawa, S.; Wang, L.; He, R.; Arimitsu, S.; Maruoka, K. Chem.-Asian J. 2014, 9, 1586
61. Quintavalla, A.; Lanza, F.; Montroni, E.; Lombardo, M.; Trombini, C. J. Org. Chem. 2013, 78, 12049
62. Geoghegan, P.; O'Leary, P. Tetrahedron: Asymmetry 2010, 21, 867
63. Bisol, T. B.; Bortoluzzi, A. J.; Sá, M. M. J. Org. Chem. 2011, 76, 948
64. Neises, B.; Steglich, W. Angew. Chem., Int. Ed. 1978, 17, 522
65. Ren, Q.; Huang, J.; Wang, L.; Li, W.; Liu, H.; Jiang, X.; Wang, J. ACS Catal. 2012, 2, 2622
66. Clave, G.; Boutal, H.; Hoang, A.; Perraut, F.; Volland, H.; Renard, P.-Y.; Romieu, A. Org. Biomol. Chem. 2008, 6, 3065
67. Chandra, K.; Dutta, D.; Das, A.; Basak, A. Bioorg. Med. Chem. 2010, 18, 8365
68. Marsault, E.; Peterson, M. L. J. Med. Chem. 2011, 54, 1961
69. Ranganathan, D.; Rao, C. B.; Ranganathan, S.; Mehrotra, A. K.; Iyengar, R. J. Org. Chem. 1980, 45, 1185
70. Zhang, X.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 8867
71. Iyer, R. A.; Hanna, P. E. Bioorg. Med. Chem. Lett. 1995, 5, 89
72. Sakamoto, M.; Kobaru, S.; Kasashima, Y.; Mino, T.; Fujita, T. Tetrahedron Lett. 2005, 46, 4439