Synthesis of tetrasubstituted cyclopentadienes via palladium-catalyzed reaction of (Z)-2-En-4-yn acetates and N-methyl indoles

Journal of Organic Chemistry

Volumn 77, Issue 23, 2012, Pages 10955-10961

  Zhong, Mei Jin ^a   Wang, Xiang Chuan ^a   Zhu, Hai Tao ^a   Hu, Jie ^a   Liu, Lei ^a   Liu, Xue Yuan ^a   Liang, Yong Min ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM;

CATALYZED REACTIONS; CYCLOPENTADIENES; PALLADIUM-CATALYZED REACTIONS; SUBSTITUTED INDOLES;

ORGANOMETALLICS;

1 METHYL 3 (1,3,5 TRIPHENYLPENT 2 EN 4 YNYL) 1H INDOLE; 1 METHYL 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE; 1 METHYL 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE 5 CARBONITRILE; 1,5 DIMETHYL 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE; 1,7 DIMETHYL 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE; 3 (1,3 DIPHENYL 5 (TRIMETHYLSILYL)PENT 2 EN 4 YNYL) 1 METHYL 1H INDOLE; 3 (2,4 DIPHENYL 5 M TOLYLCYCLOPENTA 1,4 DIENYL) 1 METHYL 1H INDOLE; 3 (2,4 DIPHENYL 5 O TOLYLCYCLOPENTA 1,4 DIENYL) 1 METHYL 1H INDOLE; 3 (2,4 DIPHENYL 5 P TOLYL CYCLOPENTA 1,4 DIENYL) 1 METHYL 1H INDOLE; 3 (2,4 DIPHENYL 5 PROPYL CYCLOPENTA 1,4 DIENYL) 1 METHYL 1H INDOLE; 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE; 3 (2,5 DIPHENYL 4 P TOLYL CYCLOPENTA 1,4 DIENYL) 1 METHYL 1H INDOLE; 3 (3 (4 CHLOROPHENYL) 1 (2,4 DICHLOROPHENYL) 5 PHENYLPENT 2 EN 4 YN 1 YL) 1 METHYL 1H INDOLE; 3 (3,5 DIPHENYL 1 PROPYL PENT 2 EN 4 YNYL) 1 METHYL 1H INDOLE; 3 (4,5 DIPHENYL 2 P TOLYL CYCLOPENTA 1,4 DIENYL) 1 METHYL 1H INDOLE; 3 [2 (4 BROMO PHENYL) 4,5 DIPHENYL CYCLOPENTA 1,4 DIENYL] 1 METHYL 1H INDOLE; 3 [2 (4 CHLORO PHENYL) 4,5 DIPHENYL CYCLOPENTA 1,4 DIENYL] 1 METHYL 1H INDOLE; 3 [4 (4 BROMO PHENYL) 2,5 DIPHENYL CYCLOPENTA 1,4 DIENYL] 1 METHYL 1H INDOLE; 3 [4 (4 CHLORO PHENYL) 2,5 DIPHENYL CYCLOPENTA 1,4 DIENYL] 1 METHYL 1H INDOLE; 3 [5 (4 CHLORO PHENYL) 2,4 DIPHENYL CYCLOPENTA 1,4 DIENYL] 1 METHYL 1H INDOLE; 3 [5 (4 METHOXY PHENYL) 2,4 DIPHENYL CYCLOPENTA 1,4 DIENYL] 1 METHYL 1H INDOLE; 4 [2 (1 METHYL 1H INDOL 3 YL) 3,4 DIPHENYL CYCLOPENTA 1,3 DIENYL] BENZONITRILE; 5 BROMO 1 METHYL 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE; 5 METHOXY 1 METHYL 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE; 5 METHYL 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE; CYCLOPENTADIENE DERIVATIVE; INDOLE DERIVATIVE; METHOXY 3 (2,4,5 TRIPHENYL CYCLOPENTA 1,4 DIENYL) 1H INDOLE; N METHYL INDOLE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 84870912756     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3021055     Document Type: Article

References (50)

1. Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409
2. Gabriele, B.; Salerno, G; Pascali, F. D.; Sciano, G. T.; Costa, M.; Chiusoli, G. P. Tetrahedron Lett. 1997, 38, 6877
3. Gabriele, B.; Salerno, G. Chem. Commun. 1997, 1083
4. Gabriele, B.; Salerno, G; Lauria, E. J. Org. Chem. 1999, 64, 7687
5. Gabriele, B.; Salerno, G.; Pascali, F. D.; Costa, M.; Chiusoli, G. P. J. Org. Chem. 1999, 64, 7693
6. Gabriele, B.; Plastina, P.; Salerno, G; Mancuso, R. Synthesis 2006, 24, 4247
7. Liu, Y.; Song, F.; Guo, S. J. Am. Chem. Soc. 2006, 128, 11332
8. Praveen, C.; Iyyappan, C.; Perumal, P. T. Tetrahedron Lett. 2010, 51, 4767
9. Obika, S.; Kono, H.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem. 2007, 72, 4462
10. Gabriele, B.; Salerno, G.; Fazio, A.; Pittelli, R. Tetrahedron 2003, 59, 6251
11. Lu, D.; Zhou, Y.; Li, Y.; Yan, S.; Gong, Y. J. Org. Chem. 2011, 76, 8869
12. Murai, M.; Uenishi, J. I.; Uemura, M. Org. Lett. 2010, 12, 4788
13. Zhang, X.; Lu, Z; Fu, C.; Ma, S. J. Org. Chem. 2010, 75, 2589
14. Bian, Y.-J.; Liu, X.-Y.; Ji, K.-G.; Shu, X.-Z.; Guo, L.-N.; Liang, Y.-M. Tetrahedron 2009, 65, 1424
15. Lu, Y.; Fu, X.; Chen, H.; Du, X.; Jia, X.; Liu, Y. Adv. Synth. Catal. 2009, 351, 129
16. Chen, Y.; Lu, Y.; Li, G.; Liu, Y. Org. Lett. 2009, 11, 3838
17. Lu, Y.; Du, X.; Jia, X.; Liu, Y. Adv. Synth. Catal. 2009, 351, 1517
18. Prasad, B. A. B.; Yoshimoto, F. K.; Sarpong, R. J. Am. Chem. Soc. 2005, 127, 12468
19. Akpinar, G. E.; Kus, M.; Karakus, E.; Artok, L. Org. Lett. 2011, 13, 748
20. Plastina, P.; Gabriele, B.; Salerno, G. Synthesis 2007, 19, 3083
21. Zhang, Y.-Q.; Chen, Z.-H.; Tu, Y.-Q.; Fan, C.-A.; Zhang, F.-M.; Wang, A.-X.; Yuan, D.-Y. Chem. Commun. 2009, 2706
22. Wang, X.-C.; Hu, J; Sun, P.-S.; Zhong, M.-J.; Ali, S.; Liang, Y.-M. Org. Biomol. Chem. 2011, 9, 7461
23. Wang, X.-C.; Yan, R.-L.; Zhong, M.-J.; Liang, Y.-M. J. Org. Chem. 2012, 77, 2064
24. Funami, H.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2007, 46, 909
25. Yeh, W.-Y. Angew. Chem., Int. Ed. 2011, 50, 12046
26. Rajakumar, P.; Kannan, A.; Sujatha, R. Synth. Commun. 1994, 24, 1847
27. Kumar, P. R. J. Chem. Soc., Chem. Commun. 1989, 8, 509
28. Mori, M.; Nojima, M.; Kusabayashi, S. J. Am. Chem. Soc. 1987, 109, 4407
29. Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction: Selected Practical Methods; Wiley: New York, 2002.
30. Kanthak, M.; Aniol, A.; Nestola, M.; Merz, K.; Oppel, I. M.; Dyker, G. Organometallics 2011, 30, 215
31. Schumann, H.; Stenz, S.; Grigsdies, F.; Muhle, S. H. Z. Naturforsch., B: J. Chem. Sci. 2002, 57, 1017
32. Xu, S.-S.; Yuan, F.; Zhuang, Y.; Wang, B.-Q.; Li, Y.-F.; Zhou, X.-Z. Inorg. Chem. Commun. 2002, 5, 102
33. Legzdins, P.; Reina, R.; Shaw, M. J.; Batchelor, R. J.; Einstein, F. W. B. Organometallics 1993, 12, 1029
34. Sonntag, N. O. V.; Linder, S.; Becker, E. I.; Spoerri, P. E. J. Am. Chem. Soc. 1953, 75, 2283
35. Davidson, A. J.; Bottini, A. T. J. Org. Chem. 1969, 34, 3641
36. Li, G.; Liu, Y. J. Org. Chem. 2010, 75, 3526
37. Datta, S.; Odedra, A.; Liu, R. S. J. Am. Chem. Soc. 2005, 127, 11606
38. Lee, J. H.; Toste, F. D. Angew. Chem., Int. Ed. 2007, 46, 912
39. Zhang, L.; Zhu, Y. N.; Yin, G. W.; Lu, P.; Wang, Y. G. J. Org. Chem. 2012, 10.1021/jo300339a
40. Chen, B.; Fan, W.; Chai, G. B.; Ma, S. Org. Lett. 2012, 14, 3616
41. Jiang, N.; Ma, Z.; Qu, Z.; Xing, X.; Xie, L.; Wang, J. J. Org. Chem. 2003, 68, 893
42. Shi, W.; Jiang, N.; Zhang, S.; Wu, W.; Du, D.; Wang, J. Org. Lett. 2003, 5, 2243
43. Shi, W.; Xiao, F.; Wang, J. J. Org. Chem. 2005, 70, 4318
44. Xiao, F.; Wang, J. J. Org. Chem. 2006, 71, 5789
45. Álvarez, E.; Miguel, D.; García-García, P.; Fernández-Rodríguez, M. A.; Rodríguez, F.; Sanz, R. Synthesis 2012, 44, 1874
46. Sanz, R.; Miguel, D.; Gohain, M.; García-García, P.; Fernández-Rodríguez, M. A.; Gonzalez-Perez, A.; Nieto-Faza, O.; De Lera, A. R.; Rodríguez, F. Chem.î-̧Eur. J. 2010, 16, 9818
47. Sanz, R.; Miguel, D.; Rodríguez, F. Angew. Chem., Int. Ed. 2008, 47, 7354
48. Kong, W.; Qiu, Y..; Zhang, X.; Fu, C.; Ma, S. Adv. Synth. Catal. 2012, 354, 2339
49. Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762
50. Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050