Copper-catalyzed tandem synthesis of indolo-, pyrrolo[2,1-a]isoquinolines, naphthyridines and bisindolo/pyrrolo[2,1-a]isoquinolines via hydroamination of ortho-haloarylalkynes followed by C-2 arylation

Journal of Organic Chemistry

Volumn 77, Issue 18, 2012, Pages 8191-8205

  Verma, Akhilesh K ^a   Jha, Rajeev R ^a   Chaudhary, Ritu ^a   Tiwari, Rakesh K ^a,b   Reddy, Kotla Siva K ^a   Danodia, Abhinandan ^a  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AIR STABLE; ARYLATIONS; BENZOTRIAZOLES; DIRECT SYNTHESIS; HETEROCYCLIC AMINES; HETEROCYCLIC COMPOUND; HYDROAMINATIONS; ISOQUINOLINES; N-ARYLATIONS; ORGANIC SINGLE CRYSTALS; REGIO-SELECTIVE; REGIOISOMERS;

AROMATIC COMPOUNDS; CATALYSIS; COPPER; FIELD EFFECT TRANSISTORS; METHANOL;

REACTION KINETICS;

COPPER; HETEROCYCLIC AMINE; ISOQUINOLINE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE;

AMINATION; ARTICLE; ARYLATION; CATALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

AMINATION; CATALYSIS; COPPER; HYDROCARBONS, HALOGENATED; INDOLES; ISOQUINOLINES; MOLECULAR STRUCTURE; NAPHTHYRIDINES; STEREOISOMERISM;

EID: 84868108610     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301572p     Document Type: Article

References (117)

1. (a) Wessjohann, L. A.; Rivera, D. G.; Vercillo, O. E. Chem. Rev. 2009, 109, 796.
2. (b) Arndtsen, B. A. Chem.-Eur. J. 2009, 15, 302.
3. (c) Jiang, B.; Rajale, T.; Wever, W.; Tu, S.-J.; Li, G. Chem.-Asian. J. 2010, 5, 2318.
4. (d) Akritopoulou-Zanze, I.; Djuric, S. W. Top. Heterocycl. Chem. 2010, 25, 231.
5. (a) Liu, X. Y.; Che, C. M. Angew. Chem., Int. Ed. 2008, 47, 3805.
6. (b) Tietze, L.F. Chem. Rev. 1996, 96, 115.
7. (c) Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302.
8. (d) Ajamain, A.; Gleason, J. L. Angew. Chem. 2004, 116, 3842;
9. (i) Angew. Chem., Int. Ed. 2004, 43, 3754.
10. (e) Wasilke, J. C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
11. (f) Meijere, A.; De.; Zezschwitz, V. P.; Brase, S. Acc. Chem. Res. 2005, 38, 413.
12. (g) Kim, J. H.; Lee, S.-G. Synthesis 2012, 44, 1464.
13. (h) Sun, L.-L.; Liao, Z.-Y.; Tang, R.-Y.; Deng, C.-L.; Zhang, X.-G. J. Org. Chem. 2012, 77, 2850.
14. (a) Mamane, V; Hannen, P.; Furstner, A. Chem.-Eur. J. 2004, 10, 4556.
15. (b) Takaya, J.; Udagawa, S.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2008, 47, 4906.
16. (c) Kusama, H.; Ishida, K.; Funami, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2008, 47, 4903.
17. (d) Umeda, N.; Tsurugi, H.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019.
18. (e) Bhunia, S.; Wang, K. C.; Liu, R. S. Angew. Chem., Int. Ed. 2008, 47, 5063.
19. (f) Kelin, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
20. (a) Pfeffer, M. Recl. Trav. Chim. Pays-Bas 1990, 109, 567.
21. (b) Spencer, J.; Pfeffer, M.; DeCian, A.; Fisher, J. J. Org. Chem. 1995, 60, 1005.
22. (c) Tsuji, J.; Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1996.
23. (a) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
24. (b) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535.
25. (c) Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.
26. (d) Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 4099.
27. (e) Isobe, H.; Cho, K.; Solin, N.; Werz, D. B.; Seeberger, P. H.; Nakamura, E. Org. Lett. 2007, 9, 4611.
28. (f) Kamijo, S.; Sasaki, Y.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 35.
29. (g) Klapars, A.; Parris, S.; Anderson, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529.
30. (h) Periasamy, M.; Vairaprakash, P.; Dalai, M. Organometallics 2008, 27, 1963.
31. (i) Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081.
32. (a) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
33. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 110, 2154.
34. (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
35. (a) Liu, Z.; Larock, R. C. J. Org. Chem. 2007, 72, 223.
36. (b) Tian, Q.; Larock, R. C. Org. Lett. 2000, 2, 3329.
37. Ewing, J.; Hughes, G. K.; Ritchie, E.; Taylor, W. C. Nature 1952, 169, 618.
38. (a) Anderson, W. K.; Heider, A. R.; Raju, N.; Yucht, J. A. J. Med. Chem. 1988, 31, 2097.
39. (b) Goldbrunner, M.; Loidl, G.; Polossek, T.; Mannschreck, A.; Angerer, E. V. J. Med. Chem. 1997, 40, 3524.
40. (c) Ambros, R.; Angerer, S. V.; Wiegrebe, W. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 743.
41. (d) Ambros, R.; Angerer, S. V.; Wiegrebe, W. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 481.
42. (a) Boden, N.; Bissell, R.; Clements, J.; Movaghar, B. Liq. Cryst. Today 1996, 6, 1.]
43. (b) Ahmed, E.; Briseno, A. L.; Xia, Y.; Jenekhe, S. A. J. Am. Chem. Soc. 2008, 130, 1118.
44. For reviews, see: (c) Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267.
45. (d) Chandrasekhar, S. Liq. Cryst. 1993, 14, 3.
46. (e) Pérez, D.; Guitián, E. Chem. Soc. Rev. 2004, 33, 274.
47. Larghi, E. L.; Obrist, B. V.; Kaufman, T. S. Tetrahedron 2008, 64, 5236.
48. Ohizumi, Y.; Kajiwara, A.; Nakamura, H.; Kobayashi, J. J. Pharm. Pharmacol. 1984, 36, 785.
49. Bernardino, A. M.; Azevedo, A. R; Pinheiro, L. C; Borges, J. C.; Paixao, I. C.; Mesquita, M.; Souza, T. M. L.; Santos, M. S. Org. Med. Chem. Lett 2012, 2, 1.
50. Johns, B. A.; Weatherhead, J. G.; Allen, S. H.; Thompson, J. B.; Garvey, E. P.; Foster, S. A.; Jeffrey, J. L.; Miller, W. H. Bioorg. Med. Chem. Lett. 2009, 19, 1802.
51. Ferrarini, P. L.; Manera, C.; Mori, C.; Badawneh, M.; Saccomanni, G. Farmaco 1998, 53, 741.
52. Clark, R. D.; Repke, D. B.A.; Kilpatrick, T.; Brown, C. M.; MacKinnon, A. C.; Clague, R. U.; Spedding, M. J. Med. Chem. 1989, 32, 2034.
53. Che, C.-M .; Wan, C.-W.; Ho, K.-Y.; Zhou, Z.-Y. New J. Chem. 2001, 25, 63.
54. (a) Orito, K.; Harada, R.; Uchiito, S.; Tokuda, M. Org. Lett. 2000, 2, 1799.
55. (b) Ambros, R.; Schneider, M. R.; Angerer, S. Von. J. Med. Chem. 1990, 33, 153.
56. (c) Orito, K.; Uchiito, S.; Satoh, Y.; Tatsuzawa, T.; Harada, R.; Takuda, M. Org. Lett. 2000, 2, 307.
57. (d) Meyers, A. I.; Sielecki, T. M. J. Am. Chem. Soc. 1991, 113, 2789.
58. (e) Vincze, Z.; Biro, A. B.; Csekei, M.; Timari, G.; Kotschy, A. Synthesis 2006, 1375.
59. (f) Barun, O.; Chakrabarti, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2001, 66, 4457.
60. (g) Reboredo, F. J.; Treus, M.; Estevez, J. C.; Castedo, L.; Estevez, R. J. Synlett. 2003, 1603.
61. (h) Menes-Arzate, M.; Martínez, R.; Cruz-Almanza, R.; Muchowski, J. M.; Osornio, Y. M.; Miranda, L. D. J. Org. Chem. 2004, 69, 4001.
62. (i) Elwan, N. M.; Abdelhadi, H. A.; Abdallah, T. A.; Hassaneen, H. M. Tetrahedron 1996, 52, 3451.
63. (j) Zhao, B.-X.; Yu, Y.; Eguchi, S. Tetrahedron 1996, 52, 12049.
64. (k) Katritzky, A. R.; Qiu, G.; Yang, B.; He, H.-Y. J. Org. Chem. 1999, 64, 7618.
65. (l) Lotter, A. N. C.; Pathak, R.; Sello, T. S.; Fernandes, M. A.; O- van, W. A. L.; Koning, de, C. B. Tetrahedron. 2007, 63, 2263.
66. (a) Han, Z.-G.; Miao, C.-B.; Shi, F.; Ma, N.; Zhang, G.; Tu, S.-J. J. Comb. Chem. 2010, 12, 16.
67. (b) Piron, K.; Kenis, S.; Verniest, G.; Surmont, R.; Thuring, J. W.; Holte, P.; Deroose, F.; Kimpe, N. D. Tetrahedron. 2012, 68, 6941.
68. (c) Janiak, C.; Deblon, S.; Uehlin, L. Synthesis 1999, 6, 959.
69. (a) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
70. (b) Severin, R.; Doye, S. Chem. Soc. Rev. 2007, 36, 1407.
71. (c) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
72. (d) Muller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795.
73. (e) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
74. (a) Fustero, S.; Rosello, M. S.; Barrio, P.; Fuentes, A. S. Chem. Rev. 2011, 111, 6984.
75. (b) Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, PR215;
76. (f) Chem. Rev. 2005, 105, 2873.
77. (c) Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433.
78. (d) Katritzky, A. R.; Rachwal, S. Chem. Rev. 2010, 110, 1564.
79. (e) Zhang, X.; Zhou, Y.; Wang, H.; Guo, D.; Ye, D.; Xu, Y.; Jiang, H.; Liu, H. Green Chem. 2011, 13, 397.
80. (a) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
81. (b) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323.
82. (c) Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633.
83. (d) Patil, N. T.; Pahadi, N. K.; Yamamoto, Y. Tetrahedron Lett. 2005, 46, 2101.
84. (a) Rodriguez, A.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 2488.
85. (b) Koradin, C.; Dohle, W.; Rodriguez, A.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
86. (c) Ackermann, L.; Song, W.; Sandmann, R. J. Organomet. Chem. 2011, 696, 195.
87. (d) Ackermann, L. Org. Lett. 2005, 7, 439.
88. (e) Kaspar, L. T.; Ackermann, L. Tetrahedron 2005, 61, 11311.
89. (f) Ackermann, L.; Sandmann, R.; Kondrashov, M. V. Synlett 2009, 8, 1219.
90. (g) Ackermann, L.; Barfuber, S.; Potukuchi, H. K. Adv. Synth. Catal. 2009, 351, 1064.
91. (h) Alsabeh, P. G.; Lundgren, R. J.; Longobardi, L. E.; Stradiotto, M. Chem. Commun. 2011, 47, 6936.
92. (i) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 5, 1823.
93. (j) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 4, 1305.
94. (k) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 31.
95. (l) Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799.
96. (m) Castro, C.; Stephens, R. J. Org. Chem. 1968, 28, 2163.
97. (a) Zhang, Y.; Donahue, J. P.; Li, C. J. Org. Lett. 2007, 9, 627.
98. (b) Zheng, Q.; Hua, R. Tetrahedron Lett. 2010, 51, 4512.
99. (a) Verma, A. K.; Singh, J.; Sankar, V. K.; Chaudhary, R.; Chandra, R. Tetrahedron Lett. 2007, 48, 4207.
100. (b) Verma, A. K.; Singh, J.; Chaudhary, R. Tetrahedron Lett. 2007, 48, 7199.
101. (c) Verma, A. K.; Singh, J.; Larock., R. C. Tetrahedron 2009, 65, 8434.
102. (a) Verma, A. K.; Aggarwal, T.; Rustagi, V.; Larock, R. C. Chem. Commun. 2010, 46, 4064.
103. (b) Verma, A. K.; Shukla, S. P.; Singh, J.; Rustagi, V. J. Org. Chem. 2011, 76, 5670.
104. (c) Rustagi, V.; Aggarwal, T.; Verma, A. K. Green Chem. 2011, 13, 1640.
105. (d) Aggarwal, T.; Imam, M.; Kaushik, N. K.; Chauhan, V. S.; Verma., A. K. ACS Comb. Sci. 2011, 13, 530.
106. Verma, A. K.; Keshwarwani, T.; Singh, J.; Tandon, V.; Larock, R. C. Angew. Chem., Int. Ed. 2009, 48, 1138.
107. (a) Verma, A. K.; Joshi, M.; Singh, V. P. Org. Lett. 2011, 13, 1630.
108. (b) Joshi, M.; Tiwari, R.; Verma, A. K. Org. Lett. 2012, 14, 1106.
109. (c) Joshi, M.; Patel, M.; Tiwari, R.; Verma, A. K. J. Org. Chem. 2012, 77, 5633.
110. Prieto, M.; Zurita, E.; Rosa, E.; Munoz, L.; Williams, P. L.; Giralt, E. J. Org. Chem. 2004, 69, 6812.
111. (a) Verma, A. K.; Joshi, M.; Singh, V. P. Org. Lett. 2011, 13, 1630.
112. (b) He, H.; Wu, Y.-Jin. Tetrahedron Lett. 2004, 45, 3237.
113. (c) Verma, A. K.; Kesharwani, T.; Singh, J.; Tandon, V.; Larock, R. C. Angew. Chem., Int. Ed. 2009, 48, 1138.
114. (d) Li, H.; Petersen, J. L.; Wang, K. K. J. Org. Chem. 2001, 66, 7804.
115. (e) Odedra, A.; Datta, S.; Liu, R.-S. J. Org. Chem. 2007, 72, 3289.
116. Tiwari, R. K.; Singh, J.; Singh, D.; Verma, A. K.; Chandra, R. Tetrahedron 2005, 61, 9513.
117. Ahmed, E.; Briseno, A. L.; Xia, Y.; Jenekhe, S. A. J. Am. Chem. Soc. 2008, 130, 1118.