Palladium-catalyzed cascade reactions of isocyanides with enaminones: Synthesis of 4-aminoquinoline derivatives

ACS Catalysis

Volumn 4, Issue 1, 2014, Pages 49-52

  Gu, Zheng Yang ^a   Zhu, Tong Hao ^a   Cao, Jia Jia ^a   Xu, Xiao Ping ^a   Wang, Shun Yi ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

amino quinoline; cascade reaction; isocyanide; palladium

Indexed keywords

AMINO QUINOLINE; CASCADE REACTIONS; DIRECT APPROACH; ENAMINONES; ISOCYANIDES; PALLADIUM-CATALYZED;

CATALYSIS; PALLADIUM;

CYANIDES;

EID: 84891785719     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs400904t     Document Type: Article

References (48)

1. Michael, J. P. Nat. Prod. Rep. 1997, 14, 605
2. Balasubramanian, M.; Keay, J. G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 5, Chapter 5.06.
3. Leue, S.; Miao, W.; Kanazawa, A.; Genisson, Y.; Garcon, S.; Greene, A. E. J. Chem. Soc., Perkin. Trans. 1 2001, 2903
4. Comins, D. L.; Nolan, J. M. Org. Lett. 2001, 3, 1611
5. Rigby, J. H.; Danca, D. M. Tetrahedron Lett. 1997, 38, 4969
6. Samosorn, S.; Bremner, J. B.; Ball, A.; Lewis, K. Bioorg. Med. Chem. 2006, 14, 857
7. Foley, M.; Tilley, L. Pharmacol. Ther. 1998, 79, 55
8. Spicer, J. A.; Gamage, S. A.; Atwell, G. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1997, 40, 1919
9. Lyon, M. A.; Lawrence, S.; William, D. J.; Jackson, Y. A. J. Chem. Soc., Perkin Trans. 1 1999, 437
10. Mirallai, S. I.; Manoli, M. L.; Koutentis, P. A. J. Org. Chem. 2013, 78, 8655
11. Singh, P. P.; Aithagani, S. K.; Yadav, M.; Singh, V. P.; Vishwakarma, R. A. J. Org. Chem. 2013, 78, 2639
12. Hakki, A.; Dillert, R.; Bahnemann, D. R. ACS Catal. 2013, 3, 565
13. Beckers, N.; Huynh, S.; Zhang, X.; Luber, E. J.; Buriak, J. M. ACS Catal. 2012, 2, 1524
14. Raynes, K. J.; Stocks, P. A.; O'Neill, P. M.; Park, B. K.; Ward, S. A. J. Med. Chem. 1999, 42, 2747
15. O'Neill, P. M.; Willock, D. J.; Hawley, S. R.; Bray, P. G.; Storr, R. C.; Ward, S. A.; Park, B. K. J. Med. Chem. 1997, 40, 437
16. Gorka, A. P.; de Dios, A.; Roepe, P. D. J. Med. Chem. 2013, 56, 5
17. Andayi, W. A.; Egan, T. J.; Gut, J.; Rosenthal, P. J.; Chibale, K. ACS Med. Chem. Lett. 2013, 4, 642
18. Gildenhuys, J.; le Roex, T.; Egan, T. J.; de Villiers, K. A. J. Am. Chem. Soc. 2013, 135, 1037
19. Combrinck, J. M.; Mabotha, T. E.; Ncokazi, K. K.; Ambele, M. A.; Taylor, D.; Smith, P. J.; Hoppe, H. C.; Egan, T. J. ACS Chem. Biol. 2013, 8, 133
20. Blackie, M. A.; Yardley, V.; Chibale, K. Bioorg. Med. Chem. Lett. 2010, 20, 1078
21. Biot, C.; Taramelli, D.; Forfar-Bares, I.; Maciejewski, L. A.; Boyce, M.; Nowogrocki, G.; Brocard, J. S.; Basilico, N.; Olliaro, P.; Egan, T. J. Mol. Pharmaceutics 2005, 2, 185
22. Biot, C.; Nosten, F.; Fraisse, L.; Ter-Minassian, D.; Khalife, J.; Dive, D. Parasite 2011, 18, 207
23. Dubar, F.; Khalife, J.; Brocard, J.; Dive, D.; Biot, C. Molecules 2008, 13, 2900
24. Trost, B. M. Science 1991, 254, 1471
25. Trost, B. M. Angew. Chem. 1995, 107, 285
26. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
27. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, U.K., 2000, p 135.
28. Matlack, A. S. Introduction to Green Chemistry; Marcel Dekker: New York, 2001, p 570.
29. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
30. Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167
31. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006; p 672.
32. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137
33. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
34. Tietze, L. F. Chem. Rev. 1996, 96, 115
35. Pellissier, H. Tetrahedron 2006, 62, 1619
36. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992; p 502.
37. Hao, W.-J.; Wang, S.-Y.; Ji, S.-J. ACS Catal. 2013, 3, 2501
38. Hao, W.-J.; Xu, X.-P.; Wang, S.-Y.; Bai, H.-W.; Ji, S.-J. Org. Lett. 2012, 14, 4894
39. Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2012, 14, 6068
40. Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2013, 15, 5226
41. Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Adv. Synth. Catal. 2013, 355, 2686
42. Wang, X.; Xu, X.-P.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2013, 15, 4246
43. Wang, X.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2013, 15, 1954
44. Zhu, T.-H.; Wang, S.-Y.; Wang, G.-N.; Ji, S.-J. Chem.-Eur. J. 2013, 19, 5850
45. Zhao, L.-L.; Wang, S.-Y.; Xu, X.-P.; Ji, S.-J. Chem. Commun. 2013, 49, 2569
46. Wang, R.; Xu, X.-P.; Meng, H.; Wang, S.-Y.; Ji, S.-J. Tetrahedron 2013, 69, 1761
47. Excellent review, see: Vlaar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem., Int. Ed. 2013, 52, 7084
48. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677