Indium-catalyzed annulation of 2-aryl- and 2-heteroarylindoles with propargyl ethers: Concise synthesis and photophysical properties of diverse aryl- and heteroaryl-annulated[a]carbazoles

Journal of the American Chemical Society

Volumn 130, Issue 47, 2008, Pages 15823-15835

  Tsuchimoto, Teruhisa ^a   Matsubayashi, Hiromichi ^b   Kaneko, Masayoshi ^b   Nagase, Yuta ^a   Miyamura, Takuhiro ^a   Shirakawa, Eiji ^c  

^a MEIJI UNIVERSITY   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC COMPOUNDS; AROMATIC HYDROCARBONS; ATOMIC PHYSICS; ATOMS; CHEMICAL REACTIONS; ETHERS; HYDROCARBONS; HYDROGEN; INDIUM; OLIGOMERS; ORGANIC COMPOUNDS; RHODIUM COMPOUNDS; SUBSTRATES; SYNTHESIS (CHEMICAL);

ALKOXY GROUPS; ANNULATION REACTIONS; ANNULATION STRATEGIES; AROMATIC RINGS; BITHIOPHENE; CARBON ATOMS; CARBON BONDS; CATALYTIC AMOUNTS; CATALYZED ANNULATIONS; CONCISE SYNTHESES; DECARBONYLATION; FISCHER INDOLE SYNTHESES; GOOD YIELDS; GREEN LIGHTS; HYDROGEN SHIFTS; MECHANISTIC STUDIES; METHYL GROUPS; NUCLEOPHILIC ATTACKS; ONE POTS; PHOTOPHYSICAL PROPERTIES; PROPARGYL ETHERS; REGIOSELECTIVE; SYNTHESIS OF; VISIBLE REGIONS;

CARBON;

BIFURAN; BITHIOPHENE; CARBAZOLE DERIVATIVE; CARBON; ETHER DERIVATIVE; FURAN DERIVATIVE; INDIUM; INDOLE DERIVATIVE; PROPARGYL ETHER; SELENIUM DERIVATIVE; SELENIUM OXIDE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; AROMATIZATION; ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; OXIDATION; SYNTHESIS;

ACIDS; ALKALOIDS; ALKYNES; CARBAZOLES; CATALYSIS; ETHERS; INDIUM; INDOLES; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; SOLVENTS;

EID: 56749149534     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803954e     Document Type: Article

References (176)

1. For reviews, see: (a) Pindur, U.; Lemster, T. Recent Res. Dev. Org. Bioorg. Chem. 1997, 1, 33-54.
2. (b) Kirsch, G. H. Curr. Org. Chem. 2001, 5, 507-518.
3. (c) Bergman, J.; Janosik, T.; Wahlstrom, N. Adv. Heterocycl. Chem. 2001, 80, 1-71.
4. (d) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303-4427.
5. (e) Fröhner, W.; Krahl, M. P.; Reddy, K. R.; Knölker, H.-J. Heterocycles 2004, 63, 2393-2407.
6. (f) Agarwal, S.; Cämmerer, S.; Filali, S.; Fröhner, W.; Knöll, J.; Krahl, M. P.; Reddy, K. R.; Knölker, H.-J. Curr. Org. Chem. 2005, 9, 1601-1614.
7. (g) Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213-7256.
8. For reviews on biological properties, see: (h) Prudhomme, M. Curr. Pharm. Des. 1997, 3, 265-290.
9. (i) Pindur, U.; Kim, Y.-S.; Mehrabani, F. Curr. Med. Chem. 1999, 6, 29-69.
10. (j) Prudhomme, M. Eur. J. Med. Chem. 2003, 38, 123-140.
11. (k) Prudhomme, M. Curr. Med. Chem.: Anti-Cancer Agents 2004, 4, 509-521.
12. See also the following report: (1) Appukkuttan, P.; Van der Eycken, E.; Dehaen, W. Synlett 2005, 127-133.
13. (a) Anizon, F.; Moreau, P.; Sancelme, M.; Voldoire, A.; Prudhomme, M.; Ollier, M.; Severe, D.; Riou, J.-F.; Bailly, C.; Fabbro, D.; Meyer, T.; Aubertin, A. M. Bioorg. Med. Chem. 1998, 6, 1597-1604.
14. (b) Moreau, P.; Sancelme, M.; Bailly, C.; Leonce, S.; Pierre, A.; Hickman, J.; Pfeiffer, B.; Prudhomme, M. Eur. J. Med. Chem. 2001, 36, 887-897.
15. (a) Tamaoki, T.; Nomoto, H.; Takahashi, I.; Kato, Y.; Morimoto, M.; Tomita, F. Biochem. Biophys. Res. Commun. 1986, 135, 397-402.
16. (b) Balamurali, R.; Prasad, K. J. R. Farmaco 2001, 56, 229-232.
17. (a) Morioka, H.; Ishihara, M.; Shibai, H.; Suzuki, T. Agric. Biol. Chem. 1985, 49, 1959-1963.
18. (b) Bush, J. A.; Long, B. H.; Catino, J. J.; Bradner, W. T.; Tomita, K. J. Antibiot. 1987, 40, 668-678.
19. (c) Fukuda, M.; Nishio, K.; Kanzawa, F.; Ogasawara, H.; Ishida, T.; Arioka, H.; Bojanowski, K.; Oka, M.; Saijo, N. Cancer Res. 1996, 56, 789-793.
20. (d) Arakawa, H.; Morita, M.; Kodera, T.; Okura, A.; Ohkubo, M.; Morishima, H.; Nishimura, S. Jpn. J. Cancer Res. 1999, 90, 1163-1170.
21. (e) Goossens, J.-F.; Hénichart, J.-P.; Anizon, F.; Prudhomme, M.; Dugave, C.; Riou, J.-F.; Bailly, C. Eur. J. Pharmacol. 2000, 389, 141-146.
22. (f) Cavazos, C. M.; Keir, S. T.; Yoshinari, T.; Bigner, D. D.; Friedman, H. S. Cancer Chemother. Pharmacol. 2001, 48, 250-254.
23. (g) Facompre, M.; Carrasco, C.; Colson, P.; Houssier, C.; Chisholm, J. D.; Van, V.; David, L.; Bailly, C. Mol. Pharmacol. 2002, 62, 1215-1227.
24. (h) Garaeva, L. D.; Bakhmedova, A. A.; Yartseva, I. V.; Melnik, S. Y.; Adanin, V. M. Russ. J. Bioorg. Chem. 2003, 29, 160-167.
25. (i) Faul, M. M.; Sullivan, K. A.; Grutsch, J. L.; Winneroski, L. L.; Shih, C.; Sanchez-Martinez, C.; Cooper, J. T. Tetrahedron Lett. 2004, 45, 1095-1098.
26. (a) Takahashi, I.; Saitoh, Y.; Yoshida, M.; Sano, H.; Nakano, H.; Morimoto, M.; Tamaoki, T. J. Antibiot. 1989, 42, 571-576.
27. (b) Kinnel, R. B.; Scheuer, P. J. J. Org. Chem. 1992, 57, 6327-6329.
28. (c) McCombie, S. W.; Bishop, R. W.; Carr, D.; Dobek, E.; Kirkup, M. P.; Kirschmeier, P.; Lin, S.-I.; Petrin, J.; Rosinski, K.; Shankar, B. B.; Wilson, O. Bioorg. Med. Chem. Lett. 1993, 3, 1537-1542.
29. (d) Vice, S. F.; Bishop, R. W.; McCombie, S. W.; Dao, H.; Frank, E.; Ganguly, A. K. Bioorg. Med. Chem. Lett. 1994, 4, 1333-1338.
30. (e) Schollmeyer, D.; Kim, Y. S.; Pindur, U. Z. Naturforsch., B: Chem. Sci. 1997, 52, 1251-1258.
31. (f) Ho, C.; Slater, S. J.; Stubbs, C. D. J. Photochem. Photobiol., A 2001, 142, 163-168.
32. (g) Shah, B. H.; Olivares-Reyes, J. A.; Catt, K. J. Mol. Pharmacol. 2005, 67, 1522-1533.
33. For pyrrolo[2,3-c]carbazole natural products, see: (a) Sato, A.; Morishita, T.; Shiraki, T.; Yoshioka, S.; Horikoshi, H.; Kuwano, H.; Hanzawa, H.; Hata, T. J. Org. Chem. 1993, 58, 7632-7634.
34. (b) Fürstner, A.; Domostoj, M. M.; Scheiper, B. J. Am. Chem. Soc. 2006, 128, 11620-11621.
35. (a) Ito, C.; Furukawa, H. Chem. Pharm. Bull. 1990, 38, 1548-1550.
36. (b) Beccalli, E. M.; Clerici, F.; Marchesini, A. Tetrahedron 1998, 54, 11675-11682.
37. (c) Soós, T.; Timári, G.; Hajós, G. Tetrahedron Lett. 1999, 40, 8607-8609.
38. (d) Knölker, H.-J.; Fröhner, W. Synthesis 2000, 2131-2136.
39. (e) Hagiwara, H.; Choshi, T.; Nobuhiro, J.; Fujimoto, H.; Hibino, S. Chem. Pharm. Bull. 2001, 49, 881-886.
40. (f) Yasuhara, A.; Suzuki, N.; Sakamoto, T. Chem. Pharm. Bull. 2002, 50, 143-145. See also references 1e and 1f.
41. (a) Wu, T.-S.; Huang, S.-C.; Wu, P.-L.; Kuoh, C.-S. Phytochemistry 1999, 52, 523-527.
42. (b) Knölker, H.-J.; Krahl, M. P. Synlett 2004, 528-530. See also references 1e and 1f.
43. Forke, R.; Krahl, M. P.; Krause, T.; Schlechtingen, G.; Knölker, H.-J. Synlett 2007, 268-272. See also reference 7a.
44. (a) Hu, N.-X.; Xie, S.; Popovic, Z.; Ong, B.; Hor, A.-M. J. Am. Chem. Soc. 1999, 121, 5097-5098.
45. (b) Hu, N.-X.; Xie, S.; Popovic, Z. D.; Ong, B.; Hor, A.-M. Synth. Met. 2000, 111-112, 421-424.
46. (c) Richter, A. M.; Hinh, L. V. Ger. Offen. DE 19831427 A1, 1983.
47. (d) Chen, J.-P. PCT Appl. WO 2003 059014 A1, 2003.
48. (e) Thomas, T.; Okada, S.; Chen, J.-P.; Furugori, M. Thin Solid Films 2003, 436, 264-268.
49. (f) Zhao, H.-P.; Tao, X.-T.; Wang, F.-Z.; Ren, Y.; Sun, X.-Q.; Yang, J.-X.; Yan, Y.-X.; Zou, D.-C.; Zhao, X.; Jiang, M.-H. Chem. Phys. Lett 2007, 439, 132-137.
50. (g) Zhao, H.-P.; Tao, X.-T.; Wang, P.; Ren, Y.; Yang, J.-X.; Yan, Y.-X.; Yuan, C.-X.; Liu, H.-J.; Zou, D.-C.; Jiang, M.-H. Org. Electron. 2007, 8, 673-682.
51. (h) Liu, H.-J.; Tao, X.-T.; Yang, J.-X.; Yan, Y.-X.; Ren, Y.; Zhao, H.-P.; Xin, Q.; Yu, W.-T.; Jiang, M.-H. Cryst. Growth Des. 2008, 8, 259-264.
52. (a) Ooyama, Y.; Shimada, Y.; Kagawa, Y.; Imae, I.; Harima, Y. Org. Biomol. Chem. 2007, 5, 2046-2054.
53. (b) Ooyama, Y.; Kagawa, Y.; Harima, Y. Eur. J. Org. Chem. 2007, 3613-3621.
54. (c) Ooyama, Y.; Shimada, Y.; Kagawa, Y.; Yamada, Y.; Imae, I.; Komaguchi, K.; Harima, Y. Tetrahedron Lett. 2007, 48, 9167-9170.
55. Lai, W.-Y.; Chen, Q.-Q.; He, Q.-Y.; Fan, Q.-L.; Huang, W. Chem. Commun. 2006, 1959-1961.
56. (a) Wakim, S.; Bouchard, J.; Simard, M.; Drolet, N.; Tao, Y.; Leclerc, M. Chem. Mater. 2004, 16, 4386-4388.
57. (b) Wu, Y.; Li, Y.; Gardner, S.; Ong, B. S. J. Am. Chem. Soc. 2005, 127, 614-618.
58. (c) Kawaguchi, K.; Nakano, K.; Nozaki, K. J. Org. Chem. 2007, 72, 5119-5128.
59. (d) Boudreault, P.-L. T.; Wakim, S.; Blouin, N.; Simard, M.; Tessier, C.; Tao, Y.; Leclerc, M. J. Am. Chem. Soc. 2007, 129, 9125-9136.
60. Wakim, S.; Bouchard, J.; Blouin, N.; Michaud, A.; Leclerc, M. Org. Lett. 2004, 6, 3413-3416.
61. Blouin, N.; Michaud, A.; Wakim, S.; Boudreault, P.-L. T.; Leclerc, M.; Vercelli, B.; Zecchin, S.; Zotti, G. Macromol. Chem. Phys. 2006, 207, 166-174.
62. (a) Curiel, D.; Cowley, A.; Beer, P. D. Chem. Commun. 2005, 236-238.
63. (b) Kim, N.-K.; Chang, K.-J.; Moon, D.; Lah, M. S.; Jeong, K.-S. Chem. Commun. 2007, 3401-3403.
64. Gómez-Lor, B.; Alonso, B.; Omenat, A.; Swrrano, J. L. Chem. Commun. 2006, 5012-5014.
65. For recent representative examples on synthesis of AHA[a]Cs. Indolo[2,3-a]carbazole: (a) Faul, M. M.; Sullivan, K. A. Tetrahedron Lett. 2001, 42, 3271-3273.
66. (b) Trost, B. M.; Krische, M. J.; Berl, V.; Grenzer, E. M. Org. Lett. 2002, 4, 2005-2008.
67. (c) Garaeva, L. D.; Bakhmedova, A. A.; Yartseva, I. V.; Melnik, S. Y.; Adanin, V. M. Russ. J. Bioorg. Chem. 2003, 29, 160-167.
68. (d) Kuethe, J. T.; Wong, A.; Davies, I. W. Org. Lett. 2003, 5, 3721-3723.
69. (e) Kuethe, J. T.; Davies, I. W. Tetrahedron Lett. 2004, 45, 4009-4012.
70. (f) Somei, M.; Yamada, F.; Suzuki, Y.; Ohmoto, S.; Hayashi, H. Heterocycles 2004, 64, 483-489.
71. (g) Cai, X.; Snieckus, V. Org. Lett. 2004, 6, 2293-2295.
72. (h) Witulski, B.; Schweikert, T. Synthesis 2005, 1959-1966.
73. (i) Pelly, S. C.; Parkinson, C. J.; van Otterlo, W. A. L.; de Koning, C. B. J. Org. Chem. 2005, 70, 10474-10481.
74. (j) Hu, Y.-Z.; Chen, Y.-Q. Synlett 2005, 42-48.
75. (k) Abbiati, G.; Arcadi, A.; Beccalli, E.; Bianchi, G.; Marinelli, F.; Rossi, E. Tetrahedron 2006, 62, 3033-3039.
76. (l) Howard-Jones, A. R.; Walsh, C. T. J. Am. Chem. Soc. 2007, 129, 11016-11017.
77. (m) Wada, Y.; Nagasaki, H.; Tokuda, M.; Orito, K. J. Org. Chem. 2007, 72, 2008-2014.
78. (n) Wilson, L. J.; Yang, C.; Murray, W. V. Tetrahedron Lett. 2007, 48, 7399-7403.
79. (o) Hinze, C.; Kreipl, A.; Terpin, A.; Steglich, W. Synthesis 2007, 608-612.
80. (p) Banerji, A.; Bandyopadhyay, D.; Basak, B.; Biswas, P. K.; Banerji, J.; Chatterjee, A. Bull. Chem. Soc. Jpn. 2007, 80, 1199-1201.
81. Indolo[3,2-a]carbazole: (q) Wahlström, N.; Bergman, J. Tetrahedron Lett. 2004, 45, 7273-7275.
82. Benzofuro[2,3-a]carbazole: (r) Hudkins, R. L.; Johnson, N. W. J. Heterocycl. Chem. 2001, 38, 591-595.
83. Benzothieno[2,3-a]carbazole: (s) Wang, J.; Soundarajan, N.; Liu, N.; Zimmermann, K.; Naidu, B. N. Tetrahedron Lett. 2005, 46, 907-910.
84. See also reference 18r. Pyrrolo[3,2-a]carbazole: (t) Pudlo, M.; Csányi, D.; Moreau, F.; Hajós, G.; Riedl, Z.; Sapi, J. Tetrahedron 2007, 63, 10320-10329.
85. Furo[3,2-a]carbazole: reference 1e. Thieno[2,3-a]carbazole: (u) Ferreira, I. C. F. R.; Queiroz, M.-J. R. P.; Kirsch, G. J. Heterocycl. Chem. 2001, 38, 749-754. Thieno[3,2-a]carbazole: reference 18i.
86. Benzo[a]carbazole: (v) de Koning, C. B.; Michael, J. P.; Rousseau, A. L. J. Chem. Soc., Perkin Trans. 1 2000, 1705-1713.
87. (w) Pindur, U.; Lemster, T. Recent Res. Dev. Org. Bioorg. Chem. 2002, 5, 99-115.
88. (x) Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556-4575.
89. (y) Yamamoto, M.; Matsubara, S. Chem. Lett. 2007, 36, 172-173. See also reference 18g.
90. (a) Beccalli, E. M.; Marchesini, A.; Pilati, T. Synthesis 1992, 891-894.
91. (b) Beccalli, E. M.; Marchesini, A. Tetrahedron 1993, 49, 4741-4758.
92. (a) Sanchez-Martinez, C.; Faul, M. M.; Shih, C. S.; Sullivan, K. A.; Grutsch, J. L.; Cooper, J. T.; Kolis, S. P. J. Org. Chem. 2003, 68, 8008-8014.
93. (b) Sanchez-Martinez, C.; Shih, C.; Faul, M. M.; Zhu, G.; Paal, M.; Somoza, C.; Li, T.; Kumrich, C. A.; Winneroski, L. L.; Kun, Z.; Brooks, H. B.; Patel, B. K. R.; Schultz, R. M.; DeHahn, T. B.; Spencer, C. D.; Watkins, S. A.; Considine, E.; Dempsey, J. A.; Ogg, C. A.; Campbell, R. M.; Anderson, B. A.; Wagner, J. Bioorg. Med. Chem. Lett. 2003, 13, 3835-3839.
94. (a) Tsuchimoto, T.; Maeda, T.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2000, 1573-1574.
95. (b) Tsuchimoto, T.; Hatanaka, K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 2454-2455.
96. For recent reviews on transition metal-catalyzed hydroarylation of alkynes, see: (a) Nevado, C.; Echavarren, A. M. Synthesis 2005, 167-182.
97. (b) Goj, L. A.; Gunnoe, T. B. Curr. Org. Chem. 2005, 9, 671-685.
98. (c) Bandini, M.; Emer, E.; Tommasi, S.; Umani-Ronchi, A. Eur. J. Org. Chem. 2006, 3527-3544.
99. (d) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333-346.
100. (e) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395-403.
101. (f) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449.
102. For other carbon-carbon bond-forming reactions through activation of π-electrons of alkynes with an indium(III) salt as a Lewis acid catalyst, see: (a) Fürstner, A.; Mamane, V. Chem. Commun. 2003, 2112-2113.
103. (b) Jiang, N.; Li, C.-J. Chem. Commun. 2004, 394-395.
104. (c) Song, C. E.; Jung, D.-U.; Choung, S. Y.; Roh, E. J.; Lee, S.-G. Angew. Chem., Int. Ed. 2004, 43, 6183-6185.
105. (d) Zang, J.; Blazecka, P. G.; Angell, P.; Lovdahl, M.; Curran, T. T. Tetrahedron 2005, 61, 7807-7813.
106. (e) Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363-1366.
107. (f) Takita, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760-13761.
108. (g) Sakai, N.; Kanada, R.; Hirasawa, M.; Konakahara, T. Tetrahedron 2005, 61, 9298-9304.
109. (h) Miyanohana, Y.; Chatani, N. Org. Lett. 2006, 8, 2155-2158.
110. (i) Sakai, N.; Annaka, K.; Konakahara, T. J. Org. Chem. 2006, 71, 3653-3655.
111. (j) Nakamura, M. Pure Appl. Chem. 2006, 78, 425-434, and Nakamura's original reports published heretofore cited therein.
112. (k) Miura, K.; Fujisawa, N.; Toyohara, S.; Hosomi, A. Synlett 2006, 1883-1886.
113. (l) Endo, K.; Hatakeyama, T.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 5264-5271.
114. (m) Tsuji, H.; Yamagata, K.; Itoh, Y.; Endo, K.; Nakamura, M.; Nakamura, E. Angew. Chem., Int. Ed. 2007, 46, 8060-8062.
115. (n) Otani, T.; Kunimatsu, S.; Nihei, H.; Abe, Y.; Saito, T. Org. Lett. 2007, 9, 5513-5516.
116. (o) Harada, S.; Takita, R.; Ohshima, T.; Matsunaga, S.; Shibasaki, M. Chem. Commun. 2007, 948-950.
117. (p) Yoon, M. Y.; Kim, J. H.; Choi, D. S.; Shin, U. S.; Lee, J. Y.; Song, C. E. Adv. Synth. Catal. 2007, 349, 1725-1737.
118. (q) Angell, P.; Blazecka, P. G.; Lovdahl, M.; Zhang, J. J. Org. Chem. 2007, 72, 6606-6609.
119. (r) Nakai, H.; Chatani, N. Chem. Lett. 2007, 36, 1494-1495.
120. (s) Peng, W.; Lee, C.-S. Synlett 2008, 142-146.
121. (t) Tsuji, H.; Fujimoto, T.; Endo, K.; Nakamura, M.; Nakamura, E. Org. Lett. 2008, 10, 1219-1221.
122. (u) Fujimoto, T.; Endo, K.; Tsuji, H.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 4492-4496.
123. (v) Sakai, N.; Annaka, K.; Fujita, A.; Sato, A.; Konokahara, T. J. Org. Chem. 2008, 73, 4160-4165, See also ref 18x.
124. For a review, see: (w) Ghosh, R.; Maiti, S. J. Mol. Catal. A: Chem. 2007, 264, 1-8.
125. (a) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. Synlett 1996, 557-559.
126. (b) Tsuchimoto, T.; Hiyama, T.; Fukuzawa, S. Chem. Commun. 1996, 2345-2346.
127. (c) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. J. Org. Chem. 1997, 62, 6997-7005.
128. Preliminary communication: Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Shirakawa, E.; Kawakami, Y. Angew. Chem., Int. Ed. 2005, 44, 1336-1340.
129. Benzo[a]carbazole 3a prepared in one step by our strategy has been known as a significant compound to exhibit a high degree of zoxazolamine hydroxylase activity in rats: (a) Buu-Hoi, N. P.; Hien, D.-P. Biochem. Pharmacol. 1968, 17, 1227-1236.
130. (b) Epstein, S. S.; Buu-Hoi, N. P.; Hein, D.-P. Cancer Res. 1971, 31, 1087-1094.
131. It has been reported that metal nonaflates (metal = Sc, Ga) exhibit higher catalytic activity than the corresponding triflate and chloride salts in the Friedel-Crafts acylation, see: (a) Matsuo, J.; Odashima, K.; Kobayashi, S. Synlett 2000, 403-405.
132. (b) Kawada, A.; Mitamura, S.; Matsuo, J.; Tsuchiya, T.; Kobayashi, S. Bull. Chem. Soc. Jpn. 2000, 73, 2325-2333.
133. Koppel, I. A.; Taft, R. W.; Anvia, F.; Zhu, S.-Z.; Hu, L.-Q.; Sung, K.-S.; Desmarteau, D. D.; Yagupolskii, L. M.; Yagupolskii, Y. L.; Ignat'ev, N. V.; Konfratenko, N. V.; Volkonskii, A. Y.; Vlasov, V. M.; Notario, R.; Maair, P.-C. J. Am. Chem. Soc. 1994, 116, 3047-3057.
134. 3 should also be soft: Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414-1417.
135. For a review of the HSAB principle, see: Ho, T.-L. Chem. Rev. 1975, 75, 1-20.
136. N-Aryl-2-phenylindoles 1h and 1i other than commercially available 1g were easily prepared from 2-phenylindole and the corresponding aryl halides according to the procedure reported by Buchwald and co-workers, see: Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684-11688.
137. Pindur, U.; Lemster, T. Recent Res. Dev. Org. Bioorg. Chem. 1997, 33-53. See also reference 1d.
138. Joule, J. A.; Mills, K. Heterocyclic Chemistry; Blackwell Science: Oxford, 2000; pp 273-295.
139. For preparation of 2,3′-biindolyl (1s), we adopted oxidative homocoupling of indole with bromine in one step, see: Robertson, N.; Parsons, S.; MacLean, E. J.; Coxall, R. A.; Mount, A. R. J. Mater. Chem. 2000, 10, 2043-2047.
140. For example, see: (a) Yoshida, S.; Fujii, M.; Aso, Y.; Otsubo, T.; Ogura, F. J. Org. Chem. 1994, 59, 3077-3081.
141. (b) Tanaka, K.; Osuga, H.; Tsujiuchi, N.; Hisamoto, M.; Sakaki, Y. Bull. Chem. Soc. Jpn. 2002, 75, 551-557.
142. (c) Akimoto, I.; Kanno, K.; Osuga, H.; Tanaka, K. J. Lumin. 2005, 112, 341-344.
143. For previous examples on synthesis of benzodithiophenes, see: (a) Gronowitz, S.; Dahlgren, T. Chem. Scr. 1977, 12, 57-67.
144. (b) Archer, W. J.; Cook, R.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1983, 813-819.
145. (c) Ryashentseva, M. A.; Minachev, K. M. Gazz. Chim. Ital. 1989, 119, 627-629.
146. (d) Sturaro, A.; Traldi, P.; Audisio, G.; Destri, S.; Catellani, M. J. HeterocycL Chem. 1990, 27, 1867-1871.
147. (e) Imamura, K.; Hirayama, D.; Yoshimura, H.; Takimiya, K.; Aso, Y.; Otsubo, T. Tetrahedron Lett. 1999, 40, 2789-2792. See also reference 35a.
148. For previous reports on synthesis of benzodifurans, see: (a) Royer, R.; Bisagni, E.; Hudry, C.; Cheutin, A.; Desvoye, M.-L. Bull. Soc. Chim. Fr. 1963, 1003-1007.
149. (b) Singh, K.; Banerjee, S. K.; Atal, C. K. Ind. J. Chem., Sect. B 1981, 20B, 108-110.
150. (c) Chandratre, S. P.; Trivedi, K. N. Ind. J. Chem., Sect. B 1987, 26B, 1148-1150.
151. (d) Soman, S. S.; Trivedi, K. N. Ind. J. Chem., Sect. B 1994, 33B, 1075-1079.
152. For example, see: (a) Martins, J. C.; Rompaey, K. V.; Wottmann, G.; Tömböly, C.; Tóth, G.; Kimpe, N. D.; Tourwé, D. J. Org. Chem. 2001, 66, 2884-2886.
153. (b) Garçon, S.; Vassiliou, S.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; Balme, G. J. Org. Chem. 2001, 66, 4069-4073.
154. (c) Mild, K.; Fujita, M.; Uemura, S.; Ohe, K. Org. Lett. 2006, 8, 1741-1743.
155. 3 in the addition of arenes to alkynes. See reference 21a.
156. (a) Gotta, M. F.; Mayr, H. J. Org. Chem. 1998, 63, 9769-9775.
157. (b) Lakhdar, S.; Westermaier, M.; Terrier, F.; Goumont, R.; Boubaker, T.; Ofial, A. R.; Mayr, H. J. Org. Chem. 2006, 71, 9088-9095.
158. (c) Joule, J. A.; Mills, K. Heterocyclic Chemistry; Blackwell Science: Oxford, 2000; pp 319-347.
159. Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th ed.; John Wiley & Sons: New York, 2007; p 322.
160. Detailed experimental procedures for the synthesis of 9-17 are provided in Supporting Information.
161. Zhang, Y.; Shibatomi, K.; Yamamoto, H. Synlett 2005, 2837-2842.
162. Regioselective mono-bromination of benzo[a]carbazoles has no precedent to the best of our knowledge. For regioselective two-step chlorination of pyrido[4,3-b]carbazoles, see: Boogaard, A. T.; Pandit, U. K.; Koomen, G.-J. Tetrahedron 1994, 50, 4811-4828.
163. Pathak, R.; Nhlapo, J. M.; Govender, S.; Michael, J. P.; van Otterlo, W. A. L.; de Koning, C. B. Tetrahedron 2006, 62, 2820-2830.
164. Wang, G.; Bergstrom, D. E. Synlett 1992, 422-424.
165. Meyer, M. D.; Kruse, L. I. J. Org. Chem. 1984, 49, 3195-3199.
166. Sumi, S.; Matsumoto, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 1891-1893.
167. Seki, K.; Ohkura, K.; Terashima, M.; Kanaoka, Y. Heterocỳ cles 1994, 37, 993-996.
168. Heaney, H.; Ley, S. V. Organic Syntheses; Wiley & Sons: New York, 1988; Collect. Vol. 6, pp 104-107.
169. (a) Nokazaki, M. Bull. Chem. Soc. Jpn. 1960, 33, 461-465.
170. (b) Snyder, L. R.; Buell, B. E. Anal. Chem. 1964, 36, 767-773.
171. (c) Promarak, V.; Saengsuwan, S.; Jungsuttiwong, S.; Sudyoadsuk, T.; Keawin, T. Tetrahedron Lett. 2007, 48, 89-93.
172. Fluorescence quantum yields of some AHA[a]Cs in degassed solution were essentially the same as those observed in non-degassed solution. Accordingly, measurements of all fluorescence spectra were carried out under non-degassed conditions.
173. Kauffman, J. M.; Litak, P. T. J. Heterocycl. Chem. 1995, 32, 1541.
174. 2) and 47 (DMSO).
175. (a) Rettig, W.; Zander, M. Chem. Phys. Lett. 1982, 87, 229-234.
176. (b) Kapturkiewicz, A.; Herbich, J.; Karpiuk, J.; Nowacki, J. J. Phys. Chem. A 1997, 101, 2332-2344.