Pd(OAc)2-catalyzed C-H activation of indoles: a facile synthesis of 3-cyanoindoles

Tetrahedron Letters

Volumn 51, Issue 25, 2010, Pages 3334-3336

  Subba Reddy, B V ^a   Begum, Zubeda ^a   Jayasudhan Reddy, Y ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

3 Cyanoindoles; C H activation; Indoles; Pd(OAc)2; Regioselective cyanation

Indexed keywords

INDOLE DERIVATIVE; NATURAL PRODUCT; NORTOPSENTIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYANATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 77953122788     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.086     Document Type: Article

References (44)

1. Sundberg R.J. Indoles (1996), Academic Press, San Diego
2. Faulkner D.J. Nat. Prod. Rep. 18 (2001) 1
3. Ninomiya I. J. Nat. Prod. 55 (1992) 541
4. Denhart D.J., Deskus J.A., Ditta J.L., Gao Q., King H.D., Kozlowski E.S., Meng Z., LaPaglia M.A., Mattson G.K., Molski T.F., Taber M.T., Lodge N.J., Mattson R.J., and Macor J.E. Bioorg. Med. Chem. Lett. (2009) 4031
5. Bandini M., Melloni A., and Umani-Ronchi A. Angew. Chem., Int. Ed. 43 (2004) 550
6. Austin J.F., and MacMillan D.W.C. J. Am. Chem. Soc. 124 (2002) 1172
7. Jensen K.B., Thorhange J., Hazel R.G., and Jorgensen K.A. Angew. Chem., Int. Ed. 40 (2001) 160
8. Srivastava N., and Banik B.K. J. Org. Chem. 68 (2003) 2109
9. Bartoli G., Bartolacci M., Bosco M., Foglia G., Giuliani A., Marcantoni E., Sambri L., and Torregiani E. J. Org. Chem. 68 (2003) 4594
10. Yoshiaki N., Masato Y., Youichi I., Masnobu H., and Sakae U. J. Am. Chem. Soc. 124 (2002) 11846
11. Wenkert E., Angell E.C., Ferreira V.F., Michelotti E.L., Piettre S.R., Sheu J.H., and Swindell C.S. J. Org. Chem. 51 (1986) 2343
12. Xiong W., Yang C., and Jiang B. Bioorg. Med. Chem. 9 (2001) 1773
13. Jiang B., and Gu X. Bioorg. Med. Chem. 8 (2000) 363
14. Rappoport Z. The Chemistry of the Cyano Group (1970), Interscience Publishers, London
15. Larock R.C. Comprehensive Organic Transformations. A Guide to Functional Group Preparations (1989), VCH Publishers, New York
16. Oishi T., Yamaguchi K., and Mizuno N. Angew. Chem., Int. Ed. 48 (2009) 6286
17. Smaliy R.V., Chaikovskaya A.A., Pinchuk A.M., and Tolmachevb A.A. Synthesis 16 (2002) 2416
18. Dohi T., Morimoto K., Takenaga N., Goto A., and Maruyam A. J. Org. Chem. 72 (2007) 109
19. Vorbruggen H., and Krolikiewicz K. Tetrahedron 50 (1994) 6549
20. Tamura Y., Kawasaki T., Adachi M., Tanio M., and Kita Y. Tetrahedron Lett. 18 (1977) 4417
21. Mehta G., Dhar D.N., and Suri S.C. Synthesis (1978) 374
22. Singh M.K., and Lakshman M.K. J. Org. Chem. 74 (2009) 3079
23. Jacqueline C.A., Graham M., Hamish M., Lovat V.C.R., and Richard T.G. Synthesis (2007) 3179
24. Jaisankar P., and Srinivasan P.C. Synthesis (2006) 2413
25. Hwu J.R., and Wong F.F. Eur. J. Org. Chem. (2006) 2513
26. Khan T.A., Peruncheralathan S., Ila H., and Junjappa H. Synlett (2004) 2019
27. Gaifa L., Nana K B., and Wayne K.A. Synlett (2001) 230
28. Ru H.J., Hao H.C., Fuh W.F., Chung-Sun C., and Gholam H.H. Synthesis (1998) 329
29. Patrice C., Andre L., and Michel M. Synthesis (1989) 451
30. Ketcha D.M., and Gribble G.W. J. Org. Chem. 50 (1985) 5451
31. Daniel D., Pierre D., and Rene R. Synthesis (1981) 739
32. Edwards J.M., and Weiss U. Tetrahedron Lett. 13 (1968) 1631
33. Pomeroy J.H., and Craig C.A. J. Am. Chem. Soc. 81 (1959) 6340
34. Jia X., Yang D., Zhang S., and Cheng J. Org. Lett. 11 (2009) 4716
35. Jia X.F., Yang D.P., Wang W.H., Luo F., and Cheng J. J. Org. Chem. 74 (2009) 9470
36. Yadav J.S., Reddy B.V.S., Chandrakanth D., and Satheesh G. Tetrahedron Lett. 48 (2007) 8040
37. Yadav J.S., Reddy B.V.S., and Praneeth K. Tetrahedron Lett. 49 (2008) 199
38. Yadav J.S., Reddy B.V.S., Raghavendra Rao K.V., and Narayana Kumar G.G.K.S. Tetrahedron Lett. 48 (2007) 5573
39. Yadav J.S., Reddy B.V.S., and Reddy Y.J. Tetrahedron Lett. 48 (2007) 7034
40. Yadav J.S., Reddy B.V.S., Narasimhulu G., Reddy N.S., Reddy P.N., Purnima K.V., Naresh P., and Jagadeesh B. Tetrahedron Lett. 51 (2010) 244
41. Yan G., Kuang C., Zhang Y., and Wang J. Org. Lett. 12 (2010) 1052
42. Obora Y., and Ishii Y. Molecules 15 (2010) 1487
43. Djakovitch L., and Rouge P. Catal. Today 140 (2009) 90
44. 2Na 224.0435, found: 224.0444.