An expedient synthesis of 3-alkylideneoxindoles by Ti(OiPr) 4/pyridine-mediated Knoevenagel condensation

Tetrahedron Letters

Volumn 55, Issue 6, 2014, Pages 1183-1187

  Lee, Hyun Ju ^a   Lim, Jin Woo ^a   Yu, Jin ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

3 Alkylideneoxindoles; Knoevenagel condensation; Ti(OiPr) 4 pyridine; Titanium enolates

Indexed keywords

EID: 84895048910     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.12.097     Document Type: Article

References (48)

1. For the synthesis of 3-alkylideneoxindoles and their biological activity, see: A. Millemaggi, and R.J.K. Taylor Eur. J. Org. Chem. 2010 4527 4547 and further references cited therein
2. C.R. Prakash, P. Theivendren, and S. Raja Pharmacol. Pharm. 3 2012 62 71
3. L. Sun, N. Tran, F. Tang, H. App, P. Hirth, G. McMahon, and C. Tang J. Med. Chem. 41 1998 2588 2603
4. For the synthetic applications of 3-alkylideneoxindole derivatives, see: S. Lin, Z.-Q. Yang, B.H.B. Kwok, M. Koldobskiy, C.M. Crews, and S.J. Danishefsky J. Am. Chem. Soc. 126 2004 6347 6355
5. T. Fukuyama, and G. Liu J. Am. Chem. Soc. 118 1996 7426 7427
6. D.B. Ramachary, C. Venkaiah, and P.M. Krishna Org. Lett. 15 2013 4714 4717
7. X.-F. Huang, Z.-M. Liu, Z.-C. Geng, S.-Y. Zhang, Y. Wang, and X.-W. Wang Org. Biomol. Chem. 10 2012 8794 8799
8. N.R. Ball-Jones, J.J. Badillo, and A.K. Franz Org. Biomol. Chem. 10 2012 5165 5181
9. B. Viswambharan, K. Selvakumar, S. Madhavan, and P. Shanmugam Org. Lett. 12 2010 2108 2111
10. X.-H. Chen, Q. Wei, S.-W. Luo, H. Xiao, and L.-Z. Gong J. Am. Chem. Soc. 131 2009 13819 13825
11. B.M. Trost, N. Cramer, and S.M. Silverman J. Am. Chem. Soc. 129 2007 12396 12397
12. W.A. Carroll, and P.A. Grieco J. Am. Chem. Soc. 115 1993 1164 1165
13. For the synthesis of 3-alkylideneoxindole derivatives under the influence of a base including amines, see: T.-P. Du, G.-G. Zhu, and J. Zhou Lett. Org. Chem. 9 2012 225 232
14. D. Villemin, and B. Martin Synth. Commun. 28 1998 3201 3208
15. H. Obase, N. Nakamizo, H. Takai, M. Teranishi, K. Kubo, K. Shuto, Y. Kasuya, K. Shigenobu, and M. Hashikami Chem. Pharm. Bull. 31 1983 3186 3197
16. Chen, L.; Feng, L.; Huang, M.; Li, J.; Nan, F.; Pang, T.; Yu, L.; Zhang, M. WO 2011/033099; Chem. Abstr. 2011, 154, 360857.
17. Bouerat, L. M. E.; Fensholdt, J.; Nielsen, S. F.; Liang, X.; Havez, S. E.; Andersson, E. C.; Jensen, L.; Hansen, J. R. WO 2005/058309, 2005; Chem. Abstr. 2005, 143, 97259
18. H. Asahara, T. Kida, T. Hinoue, and M. Akashi Tetrahedron 69 2013 9428 9433
19. W. Zhang, and M.-L. Go Bioorg. Med. Chem. 17 2009 2077 2090
20. L. Bouerat, J. Fensholdt, X. Liang, S. Havez, S.F. Nielsen, J.R. Hansen, S. Bolvig, and C. Andersson J. Med. Chem. 48 2005 5412 5414
21. P. Singh, M. Kaur, and W. Holzer Eur. J. Med. Chem. 45 2010 4968 4982
22. For the metal-catalyzed synthesis of 3-alkylideneoxindoles from their acyclic precursors, see: S. Ueda, T. Okada, and H. Nagasawa Chem. Commun. 46 2010 2462 2464
23. R. Yanada, S. Obika, Y. Kobayashi, T. Inokuma, M. Oyama, K. Yanada, and Y. Takemoto Adv. Synth. Catal. 347 2005 1632 1642
24. R. Yanada, S. Obika, T. Inokuma, K. Yanada, M. Yamashita, S. Ohta, and Y. Takemoto J. Org. Chem. 70 2005 6972 6975
25. M. Arthuis, R. Pontikis, and J.-C. Florent Tetrahedron Lett. 48 2007 6397 6400
26. W.S. Cheung, R.J. Patch, and M.R. Player J. Org. Chem. 70 2005 3741 3744
27. J.H. Park, E. Kim, and Y.K. Chung Org. Lett. 10 2008 4719 4721
28. T. Miura, T. Toyoshima, Y. Takahashi, and M. Murakami Org. Lett. 10 2008 4887 4889
29. T. Miura, Y. Takahashi, and M. Murakami Org. Lett. 9 2007 5075 5077
30. M. Inoue, T. Takahashi, H. Furuyama, and M. Hirama Synlett 2006 3037 3040
31. J. Lubkoll, A. Millemaggi, A. Perry, and R.J.K. Taylor Tetrahedron 66 2010 6606 6612
32. S. Balalaie, H. Motaghedi, M. Bararjanian, D. Tahmassebi, and H.R. Bijanzadeh Tetrahedron 67 2011 9134 9141
33. For the Pd-catalyzed arylation of 3-alkylideneoxindoles, see: H.J. Lee, K.H. Kim, S.H. Kim, and J.N. Kim Tetrahedron Lett. 54 2013 170 175
34. 4 and related titanium reagents, see: B.A. Robichaud, and K.G. Liu Tetrahedron Lett. 52 2011 6935 6938
35. L. Tichotova, E. Matousova, M. Spulak, J. Kunes, I. Votruba, V. Buchta, and M. Pour Bioorg. Med. Chem. Lett. 21 2011 6062 6066
36. A. Marrone, A. Renzetti, P. De Maria, S. Gerard, J. Sapi, A. Fontana, and N. Re Chem. Eur. J. 15 2009 11537 11550
37. K. Yamashita, T. Tanaka, and M. Hayashi Tetrahedron 61 2005 7981 7985
38. M. Hayashi, N. Nakamura, and K. Yamashita Tetrahedron 60 2004 6777 6783
39. M.T. Reetz, and M. von Itzstein J. Organomet. Chem. 334 1987 85 90
40. K. Mangala, and K. Sreekumar Appl. Organomet. Chem. 27 2013 73 78
41. Vinylogous Mukaiyama-type aldol reaction between aromatic aldehyde and 3-alkenyl-2-silyloxyindole has been reported, see: G. Rassu, V. Zambrano, R. Tanca, A. Sartori, L. Battistini, F. Zanardi, C. Curti, and G. Casiraghi Eur. J. Org. Chem. 2012 466 470
42. Vinylogous Michael addition of 3-alkylideneoxindoles to nitroolefins has also been reported, see: C. Curti, G. Rassu, V. Zambrano, L. Pinna, G. Pelosi, A. Sartori, L. Battistini, F. Zanardi, and G. Casiraghi Angew. Chem., Int. Ed. 51 2012 6200 6204
43. G. Rassu, V. Zambrano, L. Pinna, C. Curti, L. Battistini, A. Sartori, G. Pelosi, F. Zanardi, and G. Casiraghi Adv. Synth. Catal. 355 2013 1881 1886 Z-Alkylidene product was formed selectively in the reactions.
44. a data of oxindole derivatives, see: M. Ding, F. Zhou, Z.-Q. Qian, and J. Zhou Org. Biomol. Chem. 8 2010 2912 2914
45. F.G. Bordwell, and H.E. Fried J. Org. Chem. 56 1991 4218 4223
46. For the isomerization of 3-alkylideneoxindoles, see: T.-S. Jiang, R.-Y. Tang, X.-G. Zhang, X.-H. Li, and J.-H. Li J. Org. Chem. 74 2009 8834 8837
47. H. Ankati, S.K. Akubathini, S. Kamila, C. Mukherjee, S.R. D'Mello, and E.R. Biehl Open Org. Chem. J. 3 2009 1 10
48. For the photoisomerization of 3-alkylideneoxindole, see: M. Milanesio, D. Viterbo, A. Albini, E. Fasani, R. Bianchi, and M. Barzaghi J. Org. Chem. 65 2000 3416 3425