Preparation of 3-diazoindolin-2-imines via cascade reaction between indoles and sulfonylazides and their extensions to 2,3-diaminoindoles and imidazo[4,5-b]indoles

Organic Letters

Volumn 16, Issue 19, 2014, Pages 5096-5099

  Sheng, Guorong ^a   Huang, Kai ^a   Chi, Zhihao ^a   Ding, Hualong ^a   Xing, Yanpeng ^a   Lu, Ping ^a   Wang, Yanguang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZIDE; FUSED HETEROCYCLIC RINGS; IMIDAZOLE DERIVATIVE; IMINE; INDOLE DERIVATIVE; RHODIUM;

AMINATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; SYNTHESIS;

AMINATION; AMINES; AZIDES; CATALYSIS; CYCLOADDITION REACTION; HETEROCYCLIC COMPOUNDS, 3-RING; IMIDAZOLES; IMINES; INDOLES; MOLECULAR STRUCTURE; RHODIUM;

EID: 84907695493     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502423k     Document Type: Article

References (41)

1. Horning, B. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 6442
2. Gupta, S.; Kumar, B.; Kundu, B. J. Org. Chem. 2011, 76, 10154
3. Pan, E.; Oswald, N. W.; Legako, A. G.; Life, J. M.; Posner, B. A.; MacMillan, J. B. Chem. Sci. 2013, 4, 482
4. Yao, B.; Wang, Q.; Zhu, J. P. Angew. Chem., Int. Ed. 2012, 51, 5170
5. Chernyak, D.; Chernyak, N.; Gevorgyan, V. Adv. Synth. Catal. 2010, 352, 961
6. Davtyan, A. P.; Tillack, A.; Schmole, A. C.; Ortinau, S.; Frech, M. J.; Rolfs, A.; Beller, M. Org. Biomol. Chem. 2010, 8, 1149
7. Mossetti, R.; Pirali, T.; Saggiorato, D. S.; Tron, G. C. Chem. Commun. 2011, 47, 6966
8. Tron, G. C. Eur. J. Org. Chem. 2013, 1849
9. Romagnoli, R.; Baraldi, P. G.; Sarkar, T.; Carrion, M. D.; Cara, C. L.; Lopez, O. C.; Preti, D.; Tabrizi, M. A.; Tolomeo, M.; Grimaudo, S.; Cristina, A. D.; Zonta, N.; Balzarini, J.; Brancale, A.; Hsieh, H. P.; Hame, E. J. Med. Chem. 2008, 51, 1464
10. Repka, L. M.; Reisman, S. E. J. Org. Chem. 2013, 78, 12314
11. Harmon, R. E.; Stanley, F., Jr.; Gupta, S. K.; Johnson, J. J. Org. Chem. 1970, 35, 3444
12. Davies, H. M. L.; Alford, J. S. Chem. Soc. Rev. 2014, 43, 5151
13. Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed. 2012, 51, 862
14. Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972
15. Chuprakov, S.; Kwok, S. W.; Fokin, V. V. J. Am. Chem. Soc. 2013, 135, 4652
16. Schultz, E. E.; Sarpong, R. J. Am. Chem. Soc. 2013, 135, 4696
17. Chattopadhyay, B.; Gevorgyan, V. Org. Lett. 2011, 13, 3746
18. Shi, Y.; Gevorgyan, V. Org. Lett. 2013, 15, 5394
19. Selander, N.; Worrell, B. T.; Fokin, V. V. Angew. Chem., Int. Ed. 2012, 51, 13054
20. Miura, T.; Funakoshi, Y.; Morimoto, M.; Biyajima, T.; Murakami, M. J. Am. Chem. Soc. 2012, 134, 17440
21. Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2013, 52, 1371
22. Alford, J. S.; Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 11712
23. Parr, B. T.; Davies, H. M. L. Angew. Chem., Int. Ed. 2013, 52, 10044
24. Parr, B. T.; Green, S. A.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716
25. Chuprakov, S.; Kwok, S. W.; Zhang, L.; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034
26. Chuprakov, S.; Malik, J. A.; Zibinsky, M.; Fokin, V. V. J. Am. Chem. Soc. 2011, 133, 10352
27. Selander, N.; Worrell, B. T.; Chuprakov, S.; Velaparthi, S.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 14670
28. Raushel, J.; Fokin, V. Org. Lett. 2010, 12, 4952
29. Wang, F.; Fu, H.; Jiang, Y. Y.; Zhao, Y. Adv. Synth. Catal. 2008, 350, 1830
30. Cano, I.; Nicasio, M. C.; Perez, P. J. Org. Biomol. Chem. 2010, 8, 536
31. Liu, Y. T.; Wang, X. Y.; Xu, J. M.; Zhang, Q.; Zhao, Y.; Hu, Y. F. Tetrahedron 2011, 67, 6294
32. Xing, Y. P.; Sheng, G. R.; Wang, J.; Lu, P.; Wang, Y. G. Org. Lett. 2014, 16, 1244
33. Ramachary, D. B.; Ramakumar, K.; Narayana, V. V. Chem. - Eur. J. 2008, 14, 9143
34. Belkheira, M.; Abed, D. E.; Pons, J. M.; Bressy, C. Chem. - Eur. J. 2011, 17, 12917
35. Danence, L. J. T.; Gao, Y. J.; Li, M. G.; Huang, Y.; Wang, J. Chem. - Eur. J. 2011, 17, 3584
36. Wang, L.; Peng, S. Y.; Danence, L. J. T.; Gao, Y. J.; Wang, J. Chem. - Eur. J. 2012, 18, 6088
37. Wang, L.; Huang, J. Y.; Gao, X. J.; Wang, J. Chem. - Eur. J. 2013, 19, 7555
38. Contini, A.; Eraba, E. RSC Adv. 2012, 2, 10652
39. Yoo, E. J.; Chang, S. Org. Lett. 2008, 10, 1163
40. He, P.; Zhu, S. Z. J. Fluorine Chem. 2005, 126, 825
41. Bahadur, G. A.; Bailey, A. S.; Middleton, N. W.; Peach, J. M. J. Chem. Soc., Perkin Trans. 1 1980, 1689