synthesis and catalytic functionalization of biologically active indoles

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1 Palladium-catalyzed Coupling Reactions of Indoles 65 1.8 References [1] (a) R. J. Sundberg, The Chemistry of Indoles; Academic Press: New York, 1970; b) R. J. Sundberg, Indoles; Academic Press: London, 1996. [2] For recent review on indole synthesis, see. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911 and references therein. [3] S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920 and references therein. [4] For recent reviews on the synthesis of indoles, see: a) T. L. Gilchrist, J. Chem. Soc., Perkin Trans. 1 2001, 2491-2515; b) G. W. Gribble, J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075; c) U. Pindur, R. Adam, J. Heterocycl. Chem. 1988, 25, 1-8. [5] B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599-1626. [6] a) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4442-4489; Angew. Chem. 2005, 117, 4564-4601. [7] Metal-Catalyzed Cross-Coupling Reactions, 2nd Edition (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004. [8] For reviews on the Suzuki reaction see: a) Suzuki in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi), Wiley: New York, 2002, pp. 249-262; b) A. Suzuki in Metal-catalyzed Crosscoupling Reactions (Eds.; F. Diederich, P. J. Stang), VCH: Weinheim, 1998, pp. 49-97; c) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483; d) A. Suzuki, Pure Appl. Chem. 1994, 66, 213-222. [9] For more information in Suzuki-Miyaura coupling reactions see: a) A. C. Frisch, M. Beller, Angew. Chem. Int. Ed. 2005, 44, 674-688; Angew. Chem. 2005, 117, 680-695; b) J Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340-1341; c) A. Suzuki J. Organomet. Chem. 2002, 653, 83-90; d) T. Ishiyama, S. Abe, N. Miyaura, A. Suzuki, Chem. Lett. 1992, 691-694; e) R. Rossi, A. Carpita, M. G. Quirici, Tetrahedron 1981, 37, 2617-2673. [10] a) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695; b) J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire Chem. Rev. 2002, 102, 1359-1470; c) P. Lloyd-Williams, E. Giralt, Chem. Soc. Rev. 2001, 30, 145-157.
1 Palladium-catalyzed Coupling Reactions of Indoles 66 [11] R. Dandu, M. Tao, K. A. Josef, E. R. Bacon, R. L. Hudkins, J. Heterocyclic Chem. 2007, 44, 473-440. [12] R. L. Hudkins, J. L. Diebold, F. D. Marsh, J. Org. Chem. 1995, 60, 6218- 6220. [13] W. K. Goh, D. S. Black, N. Kumar, Tetrahedron Lett. 2007, 48, 9008-9011. [14] For additional information in indolones see: a) R. Martinez, A. Clara-Sosa, M. T. R. Apan, Bioorg. Med. Chem. 2007, 15, 3912-3918; b) B. Gerby, A. Boumendjel, M. Blanc, P. P. Bringuier, p. Champelovier, A. Fortune, X. Ronot, J. Boutonnat, J. Bioorg. Chem. Lett. 2007, 17, 208-213; c) S. R. Yong, A. T. Ung, S. G. Pyne, B. W. Skelton, A. H. White, Tetrahedron 2007, 63, 1191-1199. [15] K. Dairi, Y. Yao, M. Faley, S. Tripathy, E. Rioux, X. Bilot, D. Rabouin, G. Gonzalez, JF. Lavallée, G. Attardo, Org. Process Res. Dev. 2007, 11, 1051- 1054. [16] a) H. Von Dobeneck, H. Reinhard, H. Deubl, D. Wolkenstein, Chem. Ber. 1969, 102, 1357-1362. b) H. Von Dobeneck, F. Schnierle, Tetrahedron Lett. 1966, 7, 5327-5330. [17] M. Pudlo, D. Csányi, F. Moreau, G. Hajós, Z. Riedle, J. Sapi, Terahedron 2007, 63, 10320-10329. [18] For the preperation of the intermediates see: a) F. Guillier, F. Novoliers, A. Godard, F. Marsais, G. Quéguiner, M. A. Siddiqui, V. Snieckus, J. Org. Chem. 1995, 60, 292-296; b) J. J. S. Lamba, J. M. Tour, J. Am. Chem. Soc. 1994, 116, 11723-11736; c) Y. Yang, A. Martin, D. L. Nelson, J. Regan, Heterocycles 1992, 34, 1169-1177. [19] K. Nepper, S. Vanderheiden, S. Bräse, Eur. J. Org. Chem. 2006, 1886- 1898. [20] For more information in cryptaustoline and cryptowoline, see: a) M. Goldbrunner, G. Loidl, T. Polossek, A. Mannschreck, E. von Angerer, J. Med. Chem. 1997, 40, 3524-3533; b) R. Ambros, M. R. Schneider, S. von Angerer, J. Med. Chem. 1990, 33, 153-160; c) W. K. Anderson, A. R. Heider, N. Raju, J. A. Yucht, J. Med. Chem. 1988, 31, 2097-2102; d) R. Ambros, S. von Angerer, W. Wiegrebe, Arch. Pharm. (Weinheim, Ger.) 1988, 321, 743-747; e) R. Ambros, S. von Angerer, W. Wiegrebe, Arch. Pharm. (Weinheim, Ger.) 1988, 321, 481-486.
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Leibniz-Institut für Katalyse e. V
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Für meine Eltern Siegfried und Ker
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Mein besonderer Dank gilt Dr. Anneg
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Table of Contents Preface .........
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List of Abbreviations Ac Acetyl aq
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Preface The search for drugs is an
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1 Palladium-catalyzed Coupling Reac
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FULL PAPER DOI: 10.1002/ejoc.200800
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Synthesis of Potential 5-HT 6 Recep
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FULL PAPER DOI: 10.1002/ejoc.200700
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Synthesis of Indole-2,3-dicarboxyla
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3 Publications 132 3.8 Selective Re
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8 7 N R N R OH CO2Et CO2Et OH indol
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mixture was stirred at 78 C for 3 m
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3.89 (s, 2H, H-10), 4.27 (s, 2H, H-
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DOI: 10.1002/cssc.200700160 General
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Zn-Catalyzed Hydroamination of Term
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Zn-Catalyzed Hydroamination of Term
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3 Publications 146 3.10 Zn-Catalyze
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Over the past years, we investigate
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3 Publications 150 3.11 First Synth
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4608 K. Alex et al. / Tetrahedron L
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Publikationen 1 Titanium-Catalyzed
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