Unprecedented binary Cu(I)/Cu(II) catalyzed one-pot, three-component synthesis and evaluation of luminescent property of 2-Amino-3-iminoethenylidene- 2-indolones: A new class of merocyanine dye analogues

Organic Letters

Volumn 13, Issue 19, 2011, Pages 4980-4983

  Periyaraja, Somasundharam ^a   Mandal, Asit Baran ^a   Shanmugam, Ponnusamy ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80054735849     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2022164     Document Type: Article

References (74)

1. For a recent monograph, see: Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
2. Sunderhaus, J. D.; Martin, S. F. Chem.;Eur. J. 2009, 15, 1300-1308.
3. Isambert, N.; Lavilla, R. Chem.;Eur. J. 2008, 14, 8444-8454.
4. Dömling, A. Chem. Rev. 2006, 106, 17-89.
5. Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471-1499.
6. Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.;Eur. J. 2000, 6, 3321-3329.
7. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
8. Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647-658.
9. Weber, L.; Illgen, Kü.; Almstetter, M. Synlett 1999, 366-374.
10. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123-131.
11. Ugi, I.;Dömling, A.;Hörl, W. Endeavour 1994, 18, 115-122.
12. Posner, G. H. Chem. Rev. 1986, 86, 831-844.
13. For a recent monograph, see: Domino Reactions in Organic Synthesis; Tietze, L. F., Brasche, G., Gericke, K. M., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
14. Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
15. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163.
16. Tietze, L. F. J. Heterocycl. Chem. 1990, 27, 47-69.
17. Schreiber, S. L.; Burke, M. D. Angew. Chem., Int. Ed. 2004, 43, 46-58.
18. Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613-618.
19. Spring, D. R. Org. Biomol. Chem. 2003, 1, 3867-3870.
20. Arya, P.; Chou, D. T. H.; Baek, M. G. Angew. Chem., Int. Ed. 2001, 40, 339-346.
21. Cox, B.; Denyer, J. C.; Binnie, A.; Donnelly, M. C.; Evans, B.; Green, D. V. S.; Lewis, J. A.; Mander, T. H.; Merritt, A. T.; Valler, M. J.; Watson, S. P. Prog. Med. Chem. 2000, 37, 83-133.
22. Schreiber, S. L. Science 2000, 287, 1964-1969.
23. Electronic Materials: The Oligomer Approach;Müllen, K.,Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
24. For a recent monograph, see: Organic Light-Emitting Diodes- Synthesis, Properties, and Applications; Müllen, K., Scherf, U., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
25. Kim, E.; Park, S. B. Chem.;Asian J. 2009, 4, 1646-1658.
26. Cairo, C. W.; Key, J. A.; Sadek, C. M. Curr. Opin. Chem. Biol. 2010, 14, 57-63.
27. Wagenknecht, H.-A. Ann. N.Y. Acad. Sci. 2008, 1130, 122-130.
28. For a review, see:Müller, T. J. J. In Functional Organic Materials: Syntheses, Strategies, and Applications;Wiley-VCH:Weinheim, Germany, 2007; pp 179-223.
29. For a review on combinatorial syntheses of π-systems, see: Briehn, C. A.; Baüerle, P. Chem. Commun. 2002, 1015-1023.
30. D'Souza, D. M.; Müller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095-1108.
31. Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101-4111.
32. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671-2681.
33. Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2009, 74, 5476-5480.
34. Kuninobu, Y.; Inoue, Y.; Takai, K. Chem. Lett. 2007, 36, 1422-1423.
35. Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 5239-5242.
36. Ohta, Y.; Chiba, H.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2009, 74, 7052-7058.
37. Sakai, N.; Uchida, N.; Konakahara, T. Tetrahedron Lett. 2008, 49, 3437-3440.
38. Chernyak, N.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2743-2746.
39. Hamer, F. M. The Cyanine Dyes and Related Compounds; Interscience: New York, London, 1964.
40. Mishra, A.; Behera, R. K.; Behera, P. K.; Mishra, B. K.; Behera, G. B. Chem. Rev. 2000, 100, 1973-2011.
41. Kulinich, A. V.; Ishchenko, A. A. Russ. Chem. Rev. 2009, 78, 141-164.
42. Peng, X. Z. Y.; Carroll, S.; Geise, H. J.; Peng, B.; Dommisse, R.; Esmansc, E.; Carleer, R. J. Mater. Chem. 1996, 6, 1325-1333.
43. Shirinian, V. Z.; Shimkin, A. A. Top. Heterocycl. Chem. 2008, 14, 75-105.
44. Kovtun, Y. P.; Prostota, Y. O.; Shandura, M. P.; Poronik, Y. M.; Tolmachev, A. I. Dyes Pigm. 2004, 60, 215-221.
45. Kovtun, Y. P.; Prostota, Y. O.; Tolmachev, A. I. Dyes Pigm. 2003, 58, 83-91.
46. Yagi, S.; Maeda, K.; Nakazumi, H. J. Mater. Chem. 1999, 9, 2991-2997.
47. Kay, A. J.; Woolhouse, A. D.; Gainsford, G. J.; Haskell, T. G.; Barnes, T. H.; McKinnie, I. T.; Wyss, C. P. J. Mater. Chem. 2001, 11, 996-1002.
48. Würthner, F. Synthesis 1999, 2103-2113.
49. Würthner, F.; Yao, S. J. Org. Chem. 2003, 68, 8943-8949.
50. Yao, S.; Beginn, U.; Gress, T.; Lysetska, M.; Würthner, F. J. Am. Chem. Soc. 2004, 126, 8336-8346.
51. da Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12, 273-324.
52. Saxton, J. E. In The Monoterpenoid Indole Alkaloids; Wiley: New York, 1983.
53. Cordell, G. A. In The Alkaloids: Chemistry and Biology; Academic: San Diego, 1998; Vol. 5.
54. Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651-12666.
55. Xue, J.; Zhang, Y.; Wang, X.-l.; Fun, H. K.; Xu, J.-H. Org. Lett. 2000, 2, 2583-2586.
56. Klumpp, D. A.; Yeung, K. Y.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1998, 63, 4481-4484.
57. Ciganeck, E. Organic Reactions; Wiley: New York, 1997; Vol. 51, pp 201-350.
58. Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049-3052.
59. D'Souza, D. M.; Kiel, A.; Herten, D.-P.; Müller, T. J. J. Chem.;Eur. J. 2008, 14, 529-547.
60. D'Souza, D. M.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 153-158.
61. Pinto, A.; Neuville, L.; Zhu, J. Tetrahedron Lett. 2009, 50, 3602-3605.
62. Selvakumar,K.;Vaithiyanathan,V.; Shanmugam, P. Chem.Commun. 2010, 46, 2826-2828.
63. Viswambharan, B.; Selvakumar, K.;Madhavan, S.; Shanmugam, P. Org. Lett. 2010, 12, 2108-2111.
64. Muschelknautz, C.; Frank, W.; Müller, T. J. J. Org. Lett. 2011, 13, 2556-2559.
65. D'Souza, D. M.; Muschelknautz, C.; Rominger, F.; Müller, T. J. J. Org. Lett. 2010, 12, 3364-3367.
66. Zani, L.; Bolm, C. Chem. Commun. 2006, 4263-4275.
67. Pereshivko, O. P.; Peshkov, V. A.; Van der Eycken, E. V. Org. Lett. 2010, 12, 2638-2641.
68. Duran, C. F. A. G.; Moreno, I. G.; Costela, A.; Martin, V.; Sastre, R.; Banuelos, J.; Arbeloa, F. L.; Arbeloa, I. L.; Cabrera, E. P. Chem. Commun. 2010, 46, 5103-5105.
69. Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2009, 74, 5476-5480.
70. Xiao, F.; Chen, Y.; Liu, Y.; Wang, J. Tetrahedron 2008, 64, 2755-2761.
71. CCDC 806107 contains the supplementary crystallographic data. Copy of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44-1223/ 336-033; E-mail: deposit@ccdc.cam.ac.uk).
72. Kuninobu, Y.; Tokunaga, Y.; Takai, K. Chem. Lett. 2007, 36, 872-873.
73. Zhou, L.; Shi, Y.; Xiao, Q.; Liu, Y.; Ye, F.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 968-971.
74. Yamamoto, K.; Chen, Y. G.; Buono, F. G. Org. Lett. 2005, 7, 4673-4676.