Synthesis of benzocyclohepta[b]indoles by lewis acid catalyzed annulation of two 3-(1h-isochromen-1-yl)-1h-indoles

Journal of Organic Chemistry

Volumn 79, Issue 2, 2014, Pages 686-691

  Xie, Ye Xiang ^a   Tang, Ri Yuan ^a,b   Song, Ren Jie ^a   Xiang, Jian Nan ^a   Li, Jin Heng ^a  

^a HUNAN UNIVERSITY   (China)

^b WENZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

ANNULATION REACTIONS; CARBOCYCLIC RINGS; COLORIMETRIC DETECTION; LEWIS ACID;

CATALYSIS;

3 (1H ISOCHROMEN 1 YL) 1H INDOLE; 3 (3 PHENYL 1H ISOCHROMEN 1 YL) 1H INDOLE; BENZOCYCLOHEPTA[B]INDOLE; CDK INHIBITOR; COLCHICINE; COPPER; ERVATAMINE; FRONDOSIN A; INDOLE DERIVATIVE; IX 207 887; IX207 887; LEWIS ACID; MERCURY; SILICINE; UNCLASSIFIED DRUG; WELWISTATIN;

ANNULATION REACTION; ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CATALYST; COLORIMETRY; CYCLOADDITION; DRUG SYNTHESIS; ROOM TEMPERATURE; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CATALYSIS; CHROMANS; CYCLOHEPTANES; INDOLES; LEWIS ACIDS; MESYLATES; MOLECULAR STRUCTURE;

EID: 84896751343     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4024667     Document Type: Article

References (91)

1. (a) Graham, W.; Roberts, J. B. Ann. Rheum. Dis. 1953, 12, 16.
2. (b) Cocco, G.; Chu, D. C. C.; Pandolfi, S. Eur. J. Intern. Med. 2010, 21, 503.
3. Van Tamelen, E. E.; Spencer, T. A., Jr.; Allen, D. S., Jr.; Orvis, R. L. J. Am. Chem. Soc. 1959, 81, 6341.
4. Patil, A. D.; Freyer, A. J.; Killmer, L.; Offen, P.; Carte, B.; Jurewicz, A. J.; Johnson, R. K. Tetrahedron 1997, 53, 5047.
5. Trost, B. M.; Hu, Y.; Horne, D. B. J. Am. Chem. Soc. 2007, 129, 11781.
6. Bollinger, P.; Cooper, P.; Gubler, H. U.; Leutwiler, A.; Payne, T. Helv. Chim. Acta 1990, 73, 1197.
7. (g) Schnyder, J.; Bollinger, P.; Payne, T. Agents Actions 1990, 30, 350.
8. (h) Stratmann, K.; Moore, R. E.; Bonjouklian, R.; Deeter, J. B.; Patterson, G. M. L.; Shaffer, S.; Smith, C. D.; Smitka, T. A. J. Am. Chem. Soc. 1994, 116, 9935.
9. Avendano, C.; Menedez, J. C. Curr. Org. Synth. 2004, 1, 65.9.
10. The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, pp 232-239.
11. Danieli, B.; Palmisano, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 27, pp 1-130.
12. (l) Zhang, H.; Yue, J.-M. Helv. Chim. Acta 2005, 88, 2537.
13. Hong, B.-C.; Jiang, Y.-F.; Chang, Y.-L.; Lee, S.-J. J. Chin. Chem. Soc. 2006, 53, 647.
14. Bourderioux, A.; Routier, S.; Beneteau, V.; Merour, J.-Y. Tetrahedron 2007, 63, 9465. For reviews, see:
15. Battiste, M. A.; Pelphrey, P. M.; Wright, D. L. Chem. Eur. J. 2006, 12, 3438.
16. Butenschon, H. Angew. Chem., Int. Ed. 2008, 47, 5287.
17. For selected reviews, see: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
18. Katritzky, A. R.; Dennis, N. Chem. Rev. 1989, 89, 827.
19. Advances in Cycloaddition; JAI Press: Greenwich, CT, 1988-1999; Vols. 1-6.
20. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series; Pergamon: Elmsford, NY, 1990.
21. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
22. Dell, C. P. Contemp Org. Synth. 1997, 4, 87.
23. Yet, L. Chem. Rev. 2000, 100, 2963.
24. Cycloaddition Reactions in Organic Synthesis; Kobayashi, S., Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002.
25. Battiste, M. A.; Pelphrey, P. M.; Wright, D. L. Chem. Eur. J. 2006, 12, 3438.
26. Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085.
27. Lopez, F.; Mascarenas, J. L. Beilstein J. Org. Chem. 2011, 7, 1075.
28. Pellissier, H. Adv. Synth. Catal. 2011, 353, 189.
29. For special reviews on the [4 + 3] cycloaddition, see: (a) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1.
30. (b) Rigby, J. H.; Pigge, F. C. Org. React. 1997, 51, 351.
31. Harmata, M. Acc. Chem. Res. 2001, 34, 595.
32. Harmata, M.; Rashatasakhon, P. Tetrahedron 2003, 59, 2371.
33. Harmata, M. Chem. Commun. 2010, 46, 8886.
34. Lohse, A. G.; Hsung, R. P. Chem. Eur. J. 2011, 17, 3812.
35. For representative papers, see: (a) Fort, A. W. J. Am. Chem. Soc. 1962, 84, 4979.
36. Olah, G. A.; Liang, G. J. Am. Chem. Soc. 1972, 94, 6434.
37. Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1973, 12, 819.
38. Fierz, G.; Chidgey, R.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1974, 13, 410.
39. Hill, A. E.; Hoffmann, H. M. R. J. Am. Chem. Soc. 1974, 96, 4597.
40. Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. J. Am. Chem. Soc. 1975, 97, 1302.
41. Takaya, H.; Makino, S.; Hayakawa, Y.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1765.
42. (h) Giguere, R. J.; Rawson, D. I.; Hoffmann, H. M. R. Synthesis 1978, 902.
43. Sato, T.; Watanabe, M.; Noyori, R. Tetrahedron Lett. 1978, 4403.
44. White, J. D.; Fukuyama, Y. J. Am. Chem. Soc. 1979, 101, 226.
45. (k) Henning, R.; Hoffmann, H. M. R. Tetrahedron Lett. 1982, 23, 2305.
46. Mann, J.; Wilde, P. D.; Finch, M. W. J. Chem. Soc., Chem. Commun. 1985, 1543.
47. West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795.
48. Harmata, M.; Elahmad, S.; Barnes, C. L. Tetrahedron Lett. 1995, 36, 1397.
49. (o) Harmata, M.; Elomari, S.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860.
50. Trillo, B.; Lopez, F.; Gulías, M.; Castedo, L.; Mascarenas, J. L. Angew. Chem., Int. Ed. 2008, 47, 951.
51. Acharya, A.; Eickhoff, J. A.; Jeffrey, C. S. Synthesis 2013, 45, 1825.
52. Davies, H. M. L.; Dai, X. J. Am. Chem. Soc. 2004, 126, 2692.
53. Reddy, R. P.; Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 10312.
54. Lian, Y.; Miller, L. C.; Born, S.; Sarpong, R.; Davies, H. M. L. J. Am. Chem. Soc. 2010, 132, 12422.
55. Lohse, A. G.; Hsung, R. P.; Leider, M. D.; Ghosh, S. K. J. Org. Chem. 2011, 76, 3246 and references cited therein.
56. (v) Zhang, J.; Li, L.; Wang, Y.; Wang, W.; Xue, J.; Li, Y. Org. Lett. 2012, 14, 4528.
57. Han, X.; Li, H.; Hughes, R. P.; Wu, J. Angew. Chem., Int. Ed. 2012, 51, 10390.
58. Trost, B. M.; Yamazaki, S. Chem. Lett. 1994, 2245.
59. For selected papers on the synthesis of indole-containing sevenmembered rings, see: (a) Rice, L. M.; Hertz, E.; Freed, M. E. J. Med. Chem. 1964, 7, 313.
60. Vincenzocarelli, P. M.; Moracci, F. M.; Liso, G. Tetrahedron Lett. 1967, 35, 3427.
61. Perkin, W. H.; Plant, S. G. P. J. Chem. Soc. 1928, 2583.
62. Joseph, B.; Cornec, O.; Merour, J.-Y. Tetrahedron 1998, 54, 7765.
63. Kavitha, C.; Rajendra Prasad, K. J. Heterocycl. Commun. 1999, 5, 481.
64. Kupai, K.; Banoczi, G.; Hornyanszky, G.; Kolonits, P.; Novak, L. Cent. Eur. J. Chem. 2012, 10, 91.
65. Yamuna, E.; Zeller, M.; Adero, P. O.; Prasad, K. J. R. ARKIVOC 2012, 326.
66. Dange, N. S.; Hong, B.-C.; Lee, C.-C.; Lee, G.-H. Org. Lett. 2013, 15, 3914.
67. Kusama, H.; Sogo, H.; Saito, K.; Suga, T.; Iwasawa, N. Synlett 2013, 24, 1364.
68. Shu, D.; Song, W.; Li, X.; Tang, W. Angew. Chem., Int. Ed. 2013, 52, 3237.
69. Tang, R.-Y.; Guo, X.-K.; Xiang, J.-N.; Li, J.-H. J. Org. Chem. 2013, 78, 11163.
70. For selected papers, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
71. Knolker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
72. Kawasaki, T.; Higuchi, K. Nat. Prod. Rep. 2005, 22, 761.
73. (d) Bennasar, M. L.; Vidal, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340.
74. Gribble, G. W. Synlett 1991, 289.
75. Gribble, G. W. In The Alkaloids; Brossi, A., Ed.; Academic Press, Inc.: San Diego, 1990; Vol. 39, p 239.
76. Pedersen, J. M.; Bowman, W. R.; Elsegoog, M. R. J.; Fletcher, A. J.; Lovell, P. J. J. Org. Chem. 2005, 70, 10615.
77. Kuo, P. L.; Hsu, Y. L.; Kuo, Y. C.; Chang, C. H.; Lin, C. C. Cancer Lett. 2005, 223, 293.
78. Stiborova, M.; Breuer, A.; Aimova, D.; Stiborova-Rupertva, M.; Wiessler, M.; Frei, E. Int. J. Cancer 2003, 107, 885.
79. (j) Raveh, A.; Carmeli, S. J. Nat. Prod. 2007, 70, 196.
80. Mo, S.; Krunic, A.; Chlipala, G.; Orjala, J. J. Nat. Prod. 2009, 72, 894.
81. Mo, S.; Krunic, A.; Santarsiero, B. D.; Franzblau, S. G.; Orjala, J. Phytochemistry 2010, 71, 2116.
82. Yamuna, E.; Kumar, R. A.; Zeller, M.; Prasad, K. J. R. Eur. J. Med. Chem. 2012, 47, 228.
83. Tang, R.-Y.; Li, J.-H. Chem. Eur. J. 2010, 16, 4733.
84. For selected reviews and papers, see: (a) Song, Y.; Chen, Z.; Li, H. Curr. Org. Chem. 2012, 16, 2690.
85. Chen, X.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Chem. Rev. 2012, 112, 1910.
86. Ni, J.; Li, Q.; Li, B.; Zhang, L. Sensors Actuators, B: Chem. 2013, 186, 278.
87. Shi, B.; Zhang, P.; Wei, T.; Yao, H.; Lin, Q.; Liu, J.; Zhang, Y. Tetrahedron 2013, 69, 798.
88. Wang, H.-F.; Wu, S.-P. Tetrahedron 2013, 69, 1965.
89. For reviews, see: (a) Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443.
90. Zhang, J. F.; Kim, J. S. Anal. Sci. 2009, 25, 1271.
91. (c) Shi, H.; Zhao, Q.; An, Z.; Xu, W.; Liu, S.; Huang, W. Progress in Chem. 2010, 22, 1741.