synthesis and catalytic functionalization of biologically active indoles

More documents

Recommendations

Info

1 Palladium-catalyzed Coupling Reactions of Indoles 49 TIPSO CN PdCl2(PPh3) 2 CuI TIPSO CN O O O Me Me Br Br N Boc NEt3, 25 °C Br N Boc 158 156 159 Br O N N Cl H N Br N Me Me Chartelline C 161 Scheme 41. Synthesis of indole-imidazole with Sonogashira key step. Br 160 NC N Boc HN O O O Me Me OTIPS N Me Me
1 Palladium-catalyzed Coupling Reactions of Indoles 50 1.5 Buchwald-Hartwig Amination Functionalized aromatic and heteroaromatic amines are important building blocks for the synthesis of pharmaceuticals. In many areas in organic synthesis arylamines play an important role. They are not only parts in natural compounds but also in conductive polymers and photographic materials. [122] So it is not very amazing that an easy synthetic access becomes very interesting for the chemical industry. The classical exposure to these compounds is carried out by nitration- /reduction sequences or by reductive amination of aniline derivatives. These methods requires often many synthetic steps and expensive reagents. Additionally the scope for a range of functional moieties is limited because of the reaction conditions. Buchwald and Hartwig developed an effective synthesis for arylamines. Aryl halides and -triflates were coupled with amines in the presence of a palladium catalyst. The palladium-catalyzed Buchwald-Hartwig amination has matured from a synthetic laboratory procedure to a technique that is widely used in natural synthesis as well as in other fields of academic interests. Furthermore due to the versatility and reliability of this reaction, researchers in industrial environments have included this methodology in their toolbox as a standard procedure for the synthesis of amine derivatives. The process is in many points similar to palladiumcatalyzed Suzuki-, Heck-, or Stille reaction. The crucial influence for the reaction success is dependent on the catalytically active Pd(0) binding ligand. Extensive synthesis of new amino-substituted indoles is restrained due to the lack of a general regioselective method for introduction of amino-groups into this heterocycle. In recent years palladium-catalyzed arylation of amines was successfully used for building new C-N bonds. Nevertheless, this reaction still remains rare in the series of indoles and its derivatives. In all conscience there are only three publication until 2002 containing palladium-catalyzed amination of indoles. [123] Hooper et al. reported about palladium-catalyzed intermolecular amination of 2- and 3-bromoindoles in 2003. [124] They studied the activity of palladium catalysts for the amination of five-membered heterocyclic halides and determined the factors that control the scope of this reaction. Table 8 represents the amination reaction of
Page 1 and 2:
Leibniz-Institut für Katalyse e. V
Page 3 and 4:
Für meine Eltern Siegfried und Ker
Page 5 and 6:
Mein besonderer Dank gilt Dr. Anneg
Page 7 and 8:
Table of Contents Preface .........
Page 9 and 10: List of Abbreviations Ac Acetyl aq
Page 11 and 12: Preface The search for drugs is an
Page 13 and 14: 1 Palladium-catalyzed Coupling Reac
Page 59: 1 Palladium-catalyzed Coupling Reac
Page 89 and 90: 3 Publications 3.1 Titanium-Catalyz
Page 91 and 92: 1092 N. Schwarz et al. LETTER Table
Page 93 and 94: 1094 N. Schwarz et al. LETTER 2,6-d
Page 95 and 96: 3 Publications 84 3.2 Zinc-Promoted
Page 97 and 98: Table 2: Reaction of N-methyl-N-phe
Page 99 and 100: Am. Chem. Soc. 2002, 124, 15168 - 1
Page 101 and 102: A novel palladium catalyst for the
Page 103 and 104: Table 2. Reaction of different amin
Page 105 and 106: 3 Publications 94 Experimental Data
Page 107 and 108: 3 Publications 96 (q); 115.3 (d, J
Page 109 and 110: 3 Publications 98 3.4 Palladium-Cat
Page 111 and 112:
PAPER Coupling Reactions of Electro
Page 113 and 114:
Page 115 and 116:
Page 117 and 118:
Page 119 and 120:
3 Publications 108 3.5 Synthesis of
Page 121 and 122:
Scheme 2 Ti-catalyzed synthesis of
Page 123 and 124:
mixture was used for the synthesis
Page 125 and 126:
7.11 (ddd, 1H, J = 8.0 Hz, J = 7.0
Page 127 and 128:
FULL PAPER DOI: 10.1002/ejoc.200800
Page 129 and 130:
Synthesis of Potential 5-HT 6 Recep
Page 131 and 132:
Page 133 and 134:
Page 135 and 136:
Page 137 and 138:
Page 139 and 140:
FULL PAPER DOI: 10.1002/ejoc.200700
Page 141 and 142:
Synthesis of Indole-2,3-dicarboxyla
Page 143 and 144:
3 Publications 132 3.8 Selective Re
Page 145 and 146:
8 7 N R N R OH CO2Et CO2Et OH indol
Page 147 and 148:
mixture was stirred at 78 C for 3 m
Page 149 and 150:
3.89 (s, 2H, H-10), 4.27 (s, 2H, H-
Page 151 and 152:
DOI: 10.1002/cssc.200700160 General
Page 153 and 154:
Zn-Catalyzed Hydroamination of Term
Page 155 and 156:
Zn-Catalyzed Hydroamination of Term
Page 157 and 158:
3 Publications 146 3.10 Zn-Catalyze
Page 159 and 160:
Over the past years, we investigate
Page 161 and 162:
3 Publications 150 3.11 First Synth
Page 163 and 164:
4608 K. Alex et al. / Tetrahedron L
Page 165 and 166:
Publikationen 1 Titanium-Catalyzed
show all

synthesis and catalytic functionalization of biologically active indoles

You also want an ePaper? Increase the reach of your titles

Delete template?

Save as template?