Copper(II) catalyzed expeditious synthesis of furoquinoxalines through a one-pot three-component coupling strategy

Organic Letters

Volumn 16, Issue 17, 2014, Pages 4528-4531

  Naresh, Gunaganti ^a   Kant, Ruchir ^a   Narender, Tadigoppula ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,2-DIAMINOBENZENE; ALKYNE; COPPER; FUSED HETEROCYCLIC RINGS; MESYLIC ACID DERIVATIVE; PHENYLENEDIAMINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; MICROWAVE RADIATION; SYNTHESIS;

ALKYNES; CATALYSIS; COPPER; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MESYLATES; MICROWAVES; MOLECULAR STRUCTURE; PHENYLENEDIAMINES;

EID: 84914118812     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502072k     Document Type: Article

References (57)

1. Laursen, J. B.; Nielsen, J. Chem. Rev. 2004, 104, 1663
2. Katritzky, A. R.; Tymoshenko, D. O.; Monteux, D.; Vedensky, V.; Nikonov, G.; Cooper, C. B.; Deshpande, M. J. Org. Chem. 2000, 65, 8059
3. Reitz, A. B.; Gauthier, D. A.; Ho, W.; Maryanoff, B. E. Tetrahedron 2000, 56, 8809
4. Arzel, E.; Rocca, P.; Grellier, P.; Labaeïd, M.; Frappier, F.; Gueritte, F.; Gaspard, C.; Marsais, F.; Godard, A.; Queguiner, G. J. Med. Chem. 2001, 44, 949
5. Lauria, A.; Patella, C.; Dattolo, G.; Almerico, A. M. J. Med. Chem. 2008, 51, 2037
6. Dala Via, L.; Marciani, M. S.; Gia, O.; Marini, A. M.; Settimo, F. D.; Salerno, S.; Motta, C. L.; Simorini, F.; Taliani, S.; Lavecchia, A.; Giovanni, C. D.; Brancato, G.; Barone, V.; Novellino, E. J. Med. Chem. 2009, 52, 5429
7. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
8. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
9. Tietze, L. F.; Kinzel, T.; Brazel, C. C. Acc. Chem. Res. 2009, 42, 367
10. Meijere, A. D.; Zezschwitz, P. V.; Bräse, S. Acc. Chem. Res. 2005, 38, 413
11. Piou, T.; Neuville, L.; Zhu, J. Org. Lett. 2012, 14, 3760
12. Newman, S. G.; Howell, J. K.; Nicolaus, N.; Lautens, M. J. Am. Chem. Soc. 2011, 133, 14916
13. Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278
14. Vilotijevic, I.; Jamison, T. F. Angew. Chem., Int. Ed. 2009, 48, 5250
15. Padwa, A. J. Org. Chem. 2009, 74, 6421
16. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
17. Duttwyler, S.; Lu, C.; Rheingold, A. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2012, 134, 4064
18. Byers, P. M.; Alabugin, I. V. J. Am. Chem. Soc. 2012, 134, 9609
19. Williams, F. J.; Jarvo, E. R. Angew. Chem., Int. Ed. 2011, 50, 4459
20. Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2012, 41, 3790
21. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584
22. Lo, V. K. Y.; Liu, Y.; Wong, M. K.; Che, C. M. Org. Lett. 2006, 8, 1529
23. Zheng, Q.-H.; Meng, W.; Jiang, G.-J.; Yu, Z.-X. Org. Lett. 2013, 15, 5928
24. Jiang, G.-J.; Zheng, Q.-H.; Dou, M.; Zhuo, L.-G.; Meng, W.; Yu, Z.-X. J. Org. Chem. 2013, 78, 11783
25. Das, D.; Sun, A. X.; Seidel, D. Angew. Chem., Int. Ed. 2013, 52, 3765
26. Shi, S.; Wang, T.; Weingand, V.; Rudolph, M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2014, 53, 1148
27. McNulty, J.; Vemula, R.; Bordón, C.; Yolken, R.; Brando, L. J. Org. Biomol. Chem. 2014, 12, 255
28. Patil, N. T.; Nijamudheen, A.; Datta, A. J. Org. Chem. 2012, 77, 6179
29. Patil, N. T.; Raut, V. S. J. Org. Chem. 2010, 75, 6961
30. Reddy, M. S.; Thirupathi, N.; Haribabu, M. Beilstein J. Org. Chem. 2013, 9, 180
31. Cao, K.; Zhang, F.-M.; Tu, Y.-Q.; Zhuo, X.-T.; Fan, C.-A. Chem.-Eur. J. 2009, 15, 6332
32. Yamamoto, Y.; Hayashi, H.; Saigoku, T.; Nishiyama, H. J. Am. Chem. Soc. 2005, 127, 10804
33. Peshkov, V. A.; Pereshivko, O. P.; Donets, P. A.; Mehta, V. P.; Van der Eycken, E. V. Eur. J. Org. Chem. 2010, 4861
34. Reker, D.; Seet, M.; Pillong, M.; Koch, C. P.; Schneider, P.; Witschel, M. C.; Rottmann, M.; Freymond, C.; Brun, R.; Schweizer, B.; Illarionov, B.; Bacher, A.; Fischer, M.; Diederich, F.; Schneider, G. Angew. Chem., Int. Ed. 2014, 53, 1
35. Malamas, M. S.; Ni, Y.; Erdei, J.; Stange, H.; Schindler, R.; Lankau, H.-J.; Grunwald, C.; Fan, K. Y.; Parris, K.; Langen, B.; Egerland, U.; Hage, T.; Marquis, K. L.; Grauer, S.; Brennan, J.; Navarra, R.; Graf, R.; Harrison, B. L.; Robichaud, A.; Kronbach, T.; Pangalos, M. N.; Hoefgen, N.; Brandon, N. J. J. Med. Chem. 2011, 54, 7621
36. Diana, P.; Martorana, A.; Barraja, P.; Montalbano, A.; Dattolo, G.; Cirrincione, G.; Acqua, F. D.; Salvador, A.; Vedaldi, D.; Basso, G.; Viola, G. J. Med. Chem. 2008, 51, 2387
37. Butini, S.; Budriesi, R.; Hamon, M.; Morelli, E.; Gemma, S.; Brindisi, M.; Borrelli, G.; Novellino, E.; Fiorini, I.; Ioan, P.; Chiarini, A.; Cagnotto, A.; Mennini, T.; Fracasso, C.; Caccia, S.; Campiani, G. J. Med. Chem. 2009, 52, 6946
38. Achelle, S.; Baudequin, C.; Ple', N. Dyes Pigm. 2013, 98, 575
39. Zhang, Y.; Zou, J.; Yip, H.-L.; Chen, K.-S.; Zeigler, D. F.; Sun, Y.; Jen, A. K.- Y. Chem. Mater. 2011, 23, 2289
40. Brown, D. J. Quinoxalines: Supplement II. In The Chemistry of Hetercyclic Compounds; Taylor, E. C.; Wipf, P., Eds.; John Wiley & Sons: NJ, 2004.
41. Zhang, L.; Liu, G.; Zhang, S.-D.; Yang, H.-Z.; Li, L.; Wu, X.-H.; Yu, J.; Kou, B.-B.; Xu, S.; Li, J.; Sun, G.-C.; Ji, Y.-F.; Cheng, G.-F. J. Comb. Chem. 2004, 6, 431
42. Barton, D. In Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds; Barton, D.; Ollis, W. D., Eds.; Pergamon: Oxford, 1979; p 126.
43. Zhao, Z.; Wisnoski, D. D.; Wolkenberg, S. E.; Leister, W. H.; Wang, Y.; Lindsley, C. W. Tetrahedron Lett. 2004, 45, 4873
44. More, S. V.; Sastry, M. N. V.; Wang, C.-C.; Yao, C.-Y. Tetrahedron Lett. 2005, 46, 6345
45. Saifinaand, D. F.; Mamedov, V. A. Russ. Chem. Rev. 2010, 79, 351
46. Wang, W.; Shen, Y.; Meng, X.; Zhao, M.; Chen, Y.; Chen, B. Org. Lett. 2011, 13, 4514
47. Sakata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481
48. Wang, L.; Guo, W.; Zhang, X. X.; Xia, X. D.; Xiao, W. J. Org. Lett. 2012, 14, 740
49. Nakhi, A.; Rahman, Md. S.; Kumar, S. G. P.; Kumar, B. R.; Kumar, K. L.; Kulkarni, P.; Haldar, D.; Pal, M. Org. Biomol. Chem. 2013, 11, 4930
50. Li, J. J. J. Org. Chem. 1999, 64, 8425
51. Wang, P.; Xie, Z.; Wong, O.; Lee, C. S.; Wong, N.; Hung, L.; Lee, S. Chem. Commun. 2002, 1404
52. Naresh, G.; Kant, R.; Narender, T. J. Org. Chem. 2014, 79, 3821
53. Naresh, G.; Narender, T. RSC Adv. 2014, 4, 11862
54. Rajendar, K.; Ruchir, K.; Narender, T. Adv. Synth. Catal. 2013, 355, 3591
55. Narender, T.; Sarkar, S.; Rajendar, K.; Tiwari, S. Org. Lett. 2011, 13, 6140
56. CCDC No. 1011241.
57. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 36, 3769