Synthesis of CF3-containing 3,3′-cyclopropyl spirooxindoles by sequential [3 + 2] cycloaddition/ring contraction of ylideneoxindoles with 2,2,2-trifluorodiazoethane

Journal of Organic Chemistry

Volumn 79, Issue 5, 2014, Pages 2296-2302

  Li, Tian Ren ^c   Duan, Shu Wen ^c   Ding, Wei ^c   Liu, Yi Yin ^c   Chen, Jia Rong ^c   Lu, Liang Qiu ^a,b   Xiao, Wen Jing ^a,b  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b SynBio Research Platform   (China)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

CONTRACTION SEQUENCES; CYCLOPROPYL; DIASTEREO-SELECTIVITY; HIGH YIELD; TRANSITION METAL CATALYSTS;

CHEMISTRY;

ORGANIC COMPOUNDS;

2,2,2 TRIFLUORODIAZOETHANE; 3,3' CYCLOPROPYLSPIROOXINDOLE DERIVATIVE; ETHANE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; YLIDENEOXINDOLE DERIVATIVE; 2,2,2-TRIFLUORODIAZOETHANE; AZO COMPOUND; FLUORINATED HYDROCARBON; SPIRO COMPOUND;

ARTICLE; CYCLOADDITION; DIASTEREOISOMER; DRUG DESIGN; DRUG SYNTHESIS; REACTION OPTIMIZATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AZO COMPOUNDS; CATALYSIS; CYCLOADDITION REACTION; HYDROCARBONS, FLUORINATED; INDOLES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84896746970     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500019a     Document Type: Article

References (53)

1. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104
2. Zhou, F.; Liu, Y.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
3. Trost, B.; Brennan, M. Synthesis 2009, 3003
4. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
5. Bagley, J. R.; Thomas, S. A.; Rudo, F. G.; Spencer, H. K.; Doorley, B. M.; Ossipov, M. H.; Jerussi, T. P.; Benvenga, M. J.; Spaulding, T. J. Med. Chem. 1991, 34, 827
6. Schwartz, R. E.; Hirsch, C. F.; Springer, J. P.; Pettibone, D. J.; Zink, D. L. J. Org. Chem. 1987, 52, 3704
7. Robertson, D. W.; Krushinski, J. H.; Pollock, G. D.; Wilson, H.; Kauffman, R. F.; Hayes, J. S. J. Med. Chem. 1987, 30, 824
8. Helan, V.; Mills, A.; Drewry, D.; Grant, D. J. Org. Chem. 2010, 75, 6693
9. Marti, C.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 11505
10. Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186
11. He, Y.; Jiang, T.; Kuhen, K. L.; Ellis, D. A.; Wu, B.; Wu, T. Y.; Bursulaya, B. Patent WO 2004037247, 2004.
12. Ellis, D.; Kuhen, K. L.; Anaclerio, B.; Wu, B.; Wolff, K.; Yin, H.; Bursulaya, B.; Caldwell, J.; Karanewsky, D.; He, Y. Bioorg. Med. Chem. Lett. 2006, 16, 4246
13. Jiang, T.; Kuhen, K. L.; Wolff, K.; Yin, H.; Bieza, K.; Caldwell, J.; Bursulaya, B.; Wu, T. Y.; He, Y. Bioorg. Med. Chem. Lett. 2006, 16, 2105
14. Jiang, T.; Kuhen, K. L.; Wolff, K.; Yin, H.; Bieza, K.; Caldwell, J.; Bursulaya, B.; Tuntland, T.; Zhang, K.; Karanewsky, D.; He, Y. Bioorg. Med. Chem. Lett. 2006, 16, 2109
15. He, Y.; Jiang, T.; Kuhen, K. L.; Ellis, D. A.; Wu, B.; Wu, T. Y.; Bursulaya, B. U.S. Patent 7,205,328, 2007.
16. Dou, X.; Lu, Y. Chem.-Eur. J. 2012, 18, 8315
17. Lectard, S.; Hamashima, Y.; Sodeoka, M. Adv. Synth. Catal. 2010, 352, 2708
18. Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465
19. Ma, J.; Cahard, D. Chem. Rev. 2008, 108, PR1
20. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305
21. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
22. Petrov, V. A. In Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications; John Wiley & Sons: Hoboken, NJ, 2009.
23. Chen, P.; Liu, G. Synthesis 2013, 45, 2919
24. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
25. Nie, J.; Guo, H.; Cahard, D.; Ma, J. Chem. Rev. 2011, 111, 455
26. Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955
27. He, Z.; Zhang, R.; Hu, M.; Li, L.; Ni, C.; Hu, J. Chem. Sci. 2013, 4, 3478
28. Mu, X.; Wu, T.; Wang, H. Y.; Guo, Y. L.; Liu, G. J. Am. Chem. Soc. 2012, 134, 878
29. Chen, C.; Chu, L.; Qing, F. J. Am. Chem. Soc. 2012, 134, 12454
30. Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462
31. Mu, X.; Chen, S.; Zhen, X.; Liu, G. Chem.-Eur. J. 2011, 17, 6039
32. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298
33. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224
34. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
35. For a recent review of the chemistry of trifluoromethyl-substituted cyclopropanes, see: Grygorenko, O. O.; Artamonov, O. S.; Komarov, I. V.; Mykhailiuk, P. K. Tetrahedron 2011, 67, 803
36. Kunzi, S. A.; Morandi, B.; Carreira, E. M. Org. Lett. 2012, 14, 1900
37. Morandi, B.; Mariampillai, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 1101
38. Morandi, B.; Cheang, J.; Carreira, E. M. Org. Lett. 2011, 13, 3080
39. Morandi, B.; Carreira, E. M. Org. Lett. 2011, 13, 5984
40. Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 9085
41. Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 938
42. Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 4294
43. Artamonov, O.; Slobodyanyuk, E.; Shishkin, O.; Komarov, I.; Mykhailiuk, P. Synthesis 2013, 45, 225
44. Artamonov, O.; Mykhailiuk, P.; Voievoda, N.; Volochnyuk, D.; Komarov, I. Synthesis 2010, 443
45. Li, F.; Nie, J.; Sun, L.; Zheng, Y.; Ma, J. Angew. Chem., Int. Ed. 2013, 52, 6255
46. Liu, C.-B.; Meng, W.; Li, F.; Wang, S.; Nie, J.; Ma, J. Angew. Chem., Int. Ed. 2012, 51, 6227
47. Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278
48. Duan, S.-W.; Li, Y.; Liu, Y.-Y.; Zou, Y.-Q.; Shi, D.-Q.; Xiao, W.-J. Chem. Commun. 2012, 48, 5160
49. Yang, Q.-Q.; Xiao, C.; Lu, L.-Q.; An, J.; Tan, F.; Li, B.-J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 9137
50. Cheng, H.-G.; Lu, L.-Q.; Wang, T.; Yang, Q.-Q.; Liu, X.-P.; Li, Y.; Deng, Q.-H.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2013, 52, 3250
51. Wang, G.; Liu, X.; Huang, T.; Kuang, Y.-L.; Lin, L.; Feng, X. Org. Lett. 2013, 15, 76
52. Singh, A.; Loomer, A. L.; Roth, G. P. Org. Lett. 2012, 14, 5266
53. El-Sayed, M. A. A.; Abdel-Aziz, N. I.; Abdel-Aziz, A. A. M.; El-Azab, A. S.; ElTahir, K. E. H. Bioorg. Med. Chem. 2012, 20, 3306