Synthesis of 3,3-disubstituted 2-aminoindolenines by palladium-catalyzed allylic amidination with isocyanide

Synlett

Volumn 25, Issue 10, 2014, Pages 1473-1477

  Nanjo, Takeshi ^a   Tsukano, Chihiro ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

allylic amidination; cyclization; indoles; isocyanide; palladium

Indexed keywords

3,3 DISUBSTITUTED 2 AMINOINDOLENINE DERIVATIVE; CARBON; CYANIDE; INDOLE DERIVATIVE; ISOCYANIDE; PALLADIUM; UNCLASSIFIED DRUG;

AMIDINATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; MOLECULAR INTERACTION; NUCLEOPHILICITY; PHYSICAL CHEMISTRY; PROCESS DEVELOPMENT; PROCESS OPTIMIZATION; STRUCTURE ANALYSIS;

EID: 84902073354     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1341241     Document Type: Article

References (49)

1. Dewick P. M. Medicinal Natural Products: A Biosynthetic Approach. John Wiley and Sons Chichester: 2009; 3rd ed. 311 420
2. Heterocyclic Scaffolds II: Reactions and Applications of Indole In Topics in Heterocyclic Chemistry. Vol. 26 Gribble G. W. Springer Berlin: 2010
3. Eckermann R., Gaich T. Synthesis: 2013; 45 2813
4. Ishikura M., Abe T., Choshi T., Hibino S. Nat. Prod. Rep.: 2013; 30 694
5. Kawasaki T., Shinada M., Ohzono M., Ogawa A., Terashima R., Sakamoto M. J. Org. Chem.: 2008; 73 5959
6. Lindel T., Bräuchle L., Golz G., Böhrer P. Org. Lett.: 2007; 9 283
7. Fuchs J. R., Funk R. L. Org. Lett.: 2005; 7 677
8. Zhang H., Hong L., Kang H., Wang R. J. Am. Chem. Soc.: 2013; 135 14098
9. Wu H., Xue F., Xiao X., Qin Y. J. Am. Chem. Soc.: 2010; 132 14052
10. Fuchs J. R., Funk R. L. J. Am. Chem. Soc.: 2004; 126 5068
11. Ishida T., Ikota H., Kurahashi K., Tsukano C., Takemoto Y. Angew. Chem. Int. Ed.: 2013; 52 10204
12. Wu M., Ma D. Angew. Chem. Int. Ed.: 2013; 52 9759
13. Tsukano C., Okuno M., Takemoto Y. Chem. Lett.: 2013; 42 753
14. Ishida T., Tsukano C., Takemoto Y. Chem. Lett.: 2012; 41 44
15. Hande S. M., Nakajima M., Kamisaki H., Tsukano C., Takemoto Y. Org. Lett.: 2011; 13 1828
16. Yasui Y., Kamisaki H., Takemoto Y. Org. Lett.: 2008; 10 3303
17. Kobayashi Y., Kamisaki H., Yanada R., Takemoto Y. Org. Lett.: 2006; 8 2711
18. Vlaar T., Ruijter E., Maes B. U. W, Orru R. V. A. Angew. Chem. Int. Ed.: 2013; 52 7084
19. Qiu G., Ding Q., Wu J. Chem. Soc. Rev.: 2013; 42 5257
20. Lang S. Chem. Soc. Rev.: 2013; 42 4867
21. Tobisu M., Chatani N. Chem. Lett.: 2011; 40 330
22. Lygin A. V., de Meijere A. Angew. Chem. Int. Ed.: 2010; 49 9094
23. Kobayashi K., Iitsuka D., Fukamachi S., Konishi H. Tetrahedron: 2009; 65 7523
24. Tokuyama H., Fukuyama T. Chem. Rec.: 2002; 2 37
25. Fukuyama T., Chen X., Peng G. J. Am. Chem. Soc.: 1994; 116 3127
26. Jones W. D., Kosar W. P. J. Am. Chem. Soc.: 1986; 108 5640
27. Ito Y., Kobayashi K., Seko N., Saegusa T. Bull. Chem. Soc. Jpn.: 1984; 57 73
28. Ito Y., Kobayashi K., Saegusa T. J. Am. Chem. Soc.: 1977; 99 3532
29. Estévez V., Baelen G. V., Lentferink B. H., Vlaar T., Janssen E., Maes B. U. W, Orru R. V. A, Ruijter E. ACS Catal.: 2014; 4 40
30. Liu B., Gao H., Yu Y., Wu W., Jiang H. J. Org. Chem.: 2013; 78 10319
31. Vlaar T., Cioc R. C., Mampuys P., Maes B. U. W, Orru R. V. A, Ruijter E. Angew. Chem. Int. Ed.: 2012; 51 13058
32. Tyagi V., Khan S., Giri A., Gauniyal H. M., Sridhar B., Chauhan P. M. S. Org. Lett.: 2012; 14 3126
33. Wang Y., Zhu Q. Adv. Synth. Catal.: 2012; 354 1902
34. Qiu G., Liu G., Pu S., Wu J. Chem. Commun.: 2012; 48 2903
35. Baelen G. V., Kuijer S., Rýček L., Sergeyev S., Janssen E., de Kanter F. J. J, Maes B. U. W, Ruijter E., Orru R. V. A. Chem. Eur. J.: 2011; 17 15039
36. Boissarie P. J., Hamilton Z. E., Lang S., Murphy J. A., Suckling C. J. Org. Lett.: 2011; 13 6256
37. Wang Y., Wang H., Peng J., Zhu Q. Org. Lett.: 2011; 13 4604
38. Miura T., Nishida Y., Morimoto M., Yamauchi M., Murakami M. Org. Lett.: 2011; 13 1429
39. Jiang H., Liu B., Li Y., Wang A., Huang H. Org. Lett.: 2011; 13 1028
40. Tobisu M., Imoto S., Ito S., Chatani N. J. Org. Chem.: 2010; 75 4835
41. Curran D. P., Du W. Org. Lett.: 2002; 4 3215
42. Onitsuka K., Suzuki S., Takahashi S. Tetrahedron Lett.: 2002; 43 6197
43. Saluste C. G., Whitby R. J., Furber M. Angew. Chem. Int. Ed.: 2000; 39 4156
44. Nanjo T., Tsukano C., Takemoto Y. Org. Lett.: 2012; 14 4270
45. Nanjo T., Yamamoto S., Tsukano C., Takemoto Y. Org. Lett.: 2013; 15 3754
46. Park S., Shintani R., Hayashi T. Chem. Lett.: 2009; 38 204
47. Kamijo S., Yamamoto Y. J. Am. Chem. Soc.: 2002; 124 11940
48. Kamijo S., Jin T., Yamamoto Y. J. Am. Chem. Soc.: 2001; 123 9453
49. Ohe K., Matsuda H., Ishihara T., Ogoshi S., Chatani N., Murai S. J. Org. Chem.: 1993; 58 1173