Palladium-catalyzed cascade process to construct 1,2,5-trisubstituted pyrroles

Journal of Organic Chemistry

Volumn 77, Issue 8, 2012, Pages 4167-4170

  Zhang, Yong Qiang ^a   Zhu, Dao Yong ^a   Li, Bao Sheng ^a   Tu, Yong Qiang ^a   Liu, Ji Xin ^a   Lu, Yong ^a   Wang, Shao Hua ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC AMINATION; CASCADE PROCESS; HYDROAMINATIONS; PALLADIUM-CATALYZED; PRIMARY AMINES; SYNTHETIC METHODOLOGY;

CHEMISTRY; ORGANIC COMPOUNDS;

CATALYSIS;

AMINE; ENYNOL; METHYL 3 (1 ALLYL 5 METHYL 1H PYRROL 2 YL)PROPANOATE; METHYL 3 (1 BENZYL 5 METHYL 1H PYRROL 2 YL)PROPANOATE; METHYL 3 (1,5 DIBENZYL 1H PYRROL 2 YL)PROPANOATE; METHYL 3 (5 METHYL 1 (NAPHTHALEN 1 YL) 1H PYRROL 2 YL)PROPANOATE; METHYL 3 (5 METHYL 1 PHENETHYL 1H PYRROL 2 YL)PROPANOATE; METHYL 3 (5 METHYL 1 PHENYL 1H PYRROL 2 YL)PROPANOATE; METHYL 3 [1 (4 CHLOROPHENYL) 5 METHYL 1H PYRROL 2 YL]PROPANOATE; METHYL 3 [1 (4 METHOXYPHENYL) 5 METHYL 1H PYRROL 2 YL]PROPANOATE; METHYL 3 [1 (FURAN 2 YLMETHYL) 5 METHYL 1H PYRROL 2 YL]PROPANOATE; METHYL 3 [1 [2 (1H INDOL 3 YL)ETHYL] 5 METHYL 1H PYRROL 2 YL]PROPANOATE; PALLADIUM; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; METHODOLOGY; SUBSTITUTION REACTION;

EID: 84860123156     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300374v     Document Type: Article

References (45)

1. Pozharskii, A. F.; Soldatenkov, A. T.; Katritzky, A. R. Heterocycles in Life and Society; John Wiley & Sons: Chichester, 1997.
2. Walsh, C. T.; Garneau-Tsodikova, S.; Howard-Jones, A. R. Nat. Prod. Rep. 2006, 23, 517
3. Schmuck, C.; Rupprecht, D. Synthesis 2007, 3095
4. Fan, H.; Peng, J.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264
5. Gossauer, A. Pyrrole. In Houben-Weyl; Thieme: Stuttgart, 1994; E6a/1, p 556.
6. Furstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817
7. Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54
8. Sayah, B.; Pelloux-Leon, N.; Vallee, Y. J. Org. Chem. 2000, 65, 2824
9. Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587
10. Gribble, G. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 2, p 207.
11. Groenendaal, L.; Meijer, E.-W.; Vekemans, J. A. J. M. In Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, 1997.
12. Domingo, V. M.; Aleman, C.; Brillas, E.; Julia, L. J. Org. Chem. 2001, 66, 4058
13. MacDiarmid, A. G. Synth. Met. 1997, 84, 27
14. Manley, J. M.; Kalman, M. J.; Conway, M. J.; Ball, C. C.; Havens, J. L.; Vaidyanathan, R. J. J. Org. Chem. 2003, 68, 6447
15. Shiner, C. M.; Laner, T. D. Tetrahedron 2005, 61, 11628
16. Palacios, F.; Aparico, D.; de los Santos, J. M.; Vicario, J. Tetrahedron 2001, 57, 1961
17. Trautwein, A. W.; Submuth, R. D.; Jung, G. Bioorg. Med. Chem. Lett. 1998, 8, 2381
18. Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801
19. Quiclet-Sire, B.; Quintero, L.; Sanchez-Jimenez, G.; Zard, S. Z. Synlett 2003, 75
20. Tracey, M. R.; Hsung, R. P.; Lambeth, R. H. Synthesis 2004, 918
21. Lu, Y.; Fu, X.; Chen, H.; Du, X.; Jia, X.; Liu, Y. Adv. Synth. Catal. 2009, 351, 129
22. Gabriele, B.; Salerno, G.; Fazio, A. J. Org. Chem. 2003, 68, 7853
23. Du, X.; Xie, X.; Liu, Y. J. Org. Chem. 2010, 75, 510
24. Hiroya, K.; Matsumoto, S.; Ashikawa, M.; Ogiwara, K.; Sakamoto, T. Org. Lett. 2006, 8, 5349
25. Sai, M.; Matsubara, S. Org. Lett. 2011, 13, 4676
26. Ramanathan, B.; Keith, A. J.; Armstrong, D.; Odom, A. L. Org. Lett. 2004, 6, 2957
27. Istrate, F. M.; Gagosz, F. Org. Lett. 2007, 9, 3181
28. Yet, L. Chem. Rev. 2000, 100, 2963
29. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127
30. McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239
31. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079
32. Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199
33. Patil, N. T.; Yamamoto, Y. ARKIVOC 2007, 121
34. KelVin, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074
35. Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697
36. Gabriele, B.; Salerno, G.; Fazio, A. J. Org. Chem. 2003, 68, 7853
37. Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260
38. Hiroya, K.; Matsumoto, S.; Ashikawa, M.; Ogiwara, K.; Sakamoto, T. Org. Lett. 2006, 8, 5349
39. Larionov, O. V. Angew. Chem., Int. Ed. 2005, 44, 5664
40. Rakshit, S.; Patureau, F. W.; Glorious, F. J. Am. Chem. Soc. 2010, 132, 9585
41. Zhang, Y.-Q.; Chen, Z.-H.; Tu, Y.-Q.; Fan, C.-A.; Zhang, F.-M.; Wang, A.-X.; Yuan, D.-Y. Chem. Commun. 2009, 45, 2706
42. Tanikaga, R.; Takeuchi, J.; Takyu, M.; Kaji, A. J. Chem. Soc., Chem. Commun. 1987, 386
43. Müller, T. E. Tetrahedron Lett. 1998, 39, 5961
44. Lutete, L. M.; Kadota, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 1622
45. Khamwong, C.; Sakee, U. Carbohydr. Res. 2011, 346, 336