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For recent reviews on biological properties, see: d) U. Pindur, Y.-S. Kim, F. Mehrabani, Curr. Med. Chem. 1999, 6, 29-69;
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For a recent example, see: K. M. Meragelman, L. M. West, P. T. Northcote, L. K. Pannell, T. C. McKee, M. R. Boyd, J. Org. Chem. 2002, 67, 6671-6677.
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Meragelman, K.M.1
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For recent examples, see: a) C. Ho, S. J. Slater, C. D. Stubbs, J. Photochem. Photobiol. A 2001, 142, 163-168;
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Ho, C.1
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b) M. Facompre, C. Carrasco, P. Colson, C. Houssier, J. D. Chisholm, D. L. Van Vranken, C. Bailly, Mol. Pharmacol. 2002, 62, 1215-1227;
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c) F. P. Monnet, M. P. Morin-Surun, J. Leger, L. Combettes, J. Pharmacol. Exp. Ther. 2003, 307, 705-712;
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Monnet, F.P.1
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14844312176
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d) C.-H. Liao, Y.-J. Hsiech, Y.-C. Lin, Eur. J. Pharmacol. 2004, 484, 29-39.
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Liao, C.-H.1
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Lin, Y.-C.3
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0037450946
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For recent examples, see: a) S. P. Gaudêncio, M. M. M. Santos, A.M. Lobo, S. Prabhakar, Tetrahedron Lett. 2003, 44, 2577-2578;
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Santos, M.M.M.2
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Prabhakar, S.4
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0347022267
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c) M. M. Faul, K. A. Sullivan, J. L. Grutsch, L. L. Winneroski, C. Shih, C. Sanchez-Martinez, J. T. Cooper, Tetrahedron Lett. 2004, 45, 1095-1098;
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Cooper, J.T.7
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d) M. M. M. Santos, A. M. Lobo, S. Prabhakar, M. M. B. Marques, Tetrahedron Lett. 2004, 45, 2347-2349;
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16
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1442335541
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and references therein
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For furo[a]carbazoles, see: H.-J. Knölker, M. P. Krahl, Synlett 2004, 528-530, and references therein.
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Synlett
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Knölker, H.-J.1
Krahl, M.P.2
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17
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0026775778
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To the best of our knowledge, only two precedents for the synthesis of several (hetero)aryl-annulated[a]carbazoles have been reported. For the synthesis of benzo-, thieno-, and pyrrolo[a]carbazoles using photochemical cyclization of 3-(2-styryl)indoles, see: a) E. M. Beccali, A. Marchesini, T. Pilati, Synthesis 1992, 891-894.
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Synthesis
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Beccali, E.M.1
Marchesini, A.2
Pilati, T.3
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18
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0142058549
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For the synthesis of benzo-, naphtho-, thieno-, and benzothieno[a] carbazoles using photochemical cyclization of 3-indolyl-4-arylmaleimides or the Mizoroki-Heck-type cyclization of 3-indolyl-4-(2-bromoaryl)maleimides, see: b) C. Sanchez-Martinez, M. M. Faul, C. Shih, K. A. Sullivan, J. L. Grutsch, J. T. Cooper, S. P. Kolis, J. Org. Chem. 2003, 68, 8008-8014.
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J. Org. Chem.
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Sanchez-Martinez, C.1
Faul, M.M.2
Shih, C.3
Sullivan, K.A.4
Grutsch, J.L.5
Cooper, J.T.6
Kolis, S.P.7
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19
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0038798399
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For example, see: a) R. L. Shriner, W. C. Ashley, E. Welch, Org. Synth. Coll. Vol. 3 1955, 725-727;
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Org. Synth. Coll. Vol. 3
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Shriner, R.L.1
Ashley, W.C.2
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20
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0022350560
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b) K. C. Joshi, R. Jain, S. Garg, J. Indian Chem. Soc. 1985, 62, 388-390;
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J. Indian Chem. Soc.
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Joshi, K.C.1
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22
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33947298530
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For a review, see: d) B. Robinson, Chem. Rev. 1969, 69, 227-250.
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Chem. Rev.
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Robinson, B.1
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23
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0034618620
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We recently demonstrated that a C-H bond of arenes and heterocyclic arenes adds to alkynes in the presence of a metal triflate catalyst, see: a) T. Tsuchimoto, T. Maeda, E. Shirakawa, Y. Kawakami, Chem. Commun. 2000, 1573-1574;
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Chem. Commun.
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Tsuchimoto, T.1
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24
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0142074710
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b) T. Tsuchimoto, K. Hatanaka, E. Shirakawa, Y. Kawakami, Chem. Commun. 2003, 2454-2455.
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Chem. Commun.
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Tsuchimoto, T.1
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Kawakami, Y.4
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25
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0040753494
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We previously reported that metal triflates catalyze the substitution reaction of the C-O bond of alcohols and acetals with arenes, see: a) T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, Synlett 1996, 557-559;
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Synlett
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Tsuchimoto, T.1
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0000284687
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c) T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, J. Org. Chem. 1997, 62, 6997-7005.
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Tsuchimoto, T.1
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Fukuzawa, S.4
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28
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14844331129
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note
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3 is commercially available from Aldrich.
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-
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29
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14844293609
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note
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3H in an easy manner. For details, see Supporting Information.
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30
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0034093339
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It has been reported that gallium nonaflate exhibits higher catalytic activity than the corresponding triflate and chloride salts in the Friedel-Crafts acylation reactions, see: J. Matsuo, K. Odashima, S. Kobayashi, Synlett 2000, 403-405.
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(2000)
Synlett
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Matsuo, J.1
Odashima, K.2
Kobayashi, S.3
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31
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0037154820
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3 in the cycloisomerization of ω-aryl-1-alkynes. As indium is located below gallium in the periodic table, indium nonaflate should also be soft: H. Inoue, N. Chatani, S. Murai, J. Org. Chem. 2002, 67, 1414-1417. For a review of hard and soft acids and bases (HSAB) principle, see: T.-L. Ho, Chem. Rev. 1975, 75, 1-20.
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Inoue, H.1
Chatani, N.2
Murai, S.3
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32
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33847800887
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3 in the cycloisomerization of ω-aryl-1-alkynes. As indium is located below gallium in the periodic table, indium nonaflate should also be soft: H. Inoue, N. Chatani, S. Murai, J. Org. Chem. 2002, 67, 1414-1417. For a review of hard and soft acids and bases (HSAB) principle, see: T.-L. Ho, Chem. Rev. 1975, 75, 1-20.
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Chem. Rev.
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Ho, T.-L.1
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33
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0028283845
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For the synthesis of a homodimer such as 2,2′-bis(N-methyl-indolyl) (1k), oxidative homocoupling of N-methylindole is more straightforward, see: U. Pindur, Y.-S. Kim, D. Schollmeyer, J. Heterocycl. Chem. 1994, 31, 377-386.
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0011977611
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See also reference [1c]
-
The benzo[a]carbazole 3ba is known to exhibit pronounced antitumor activity against, for example, leukemia, renal tumor, and colon cancer, see: U. Pindur, T. Lemster, Recent Res. Dev. Org. Bioorg. Chem. 1997, 33-53. See also reference [1c].
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Pindur, U.1
Lemster, T.2
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35
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0001626633
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Alkoxy groups of alkenyl and aryl ethers have been reportedly transformed into alkyl and aryl groups by using Grignard reagents in the presence of a nickel catalyst, see: E. Wenkert, E. L. Michelotti, C. S. Swindell, M. Tingoli, J. Org. Chem. 1984, 49, 4894-4899.
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Wenkert, E.1
Michelotti, E.L.2
Swindell, C.S.3
Tingoli, M.4
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36
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14844337159
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note
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1H COSY and NOESY NMR techniques.
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-
-
-
38
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0004061172
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-
Blackwell Science, Oxford
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b) J. A. Joule, K. Mills, Heterocyclic Chemistry, Blackwell Science, Oxford, 2000, pp. 324-379.
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Joule, J.A.1
Mills, K.2
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39
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14844315133
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-
note
-
2H NMR spectrum showed no incorporation of the deuterium atom at the other carbon atoms.
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