Indoles constitute important heterocyclic systems in nature. Based on the broad structural diversity and due to their biological activity, indoles have become an important component in several current pharmaceutical drugs. Hence, the development of improved synthetic methodologies for the generation of the indole core, as well as functionalization reactions on the aromatic ring system continue to be of significant interest to organic chemists. Among the numerous known bioactive indoles, various N-alkylated derivatives are known. The classical approach for the introduction of these alkyl chains involves treatment of the indole with base and an alkyl halide. A drawback of these reactions is the quantitative formation of waste salts. Clearly, this disadvantage can be overcome by using easily available alcohols as a more benign alkyl source. However, so far, the N-alkylation of indoles with alcohols has only been investigated in the presence of Raney nickel. More recently, Grigg and co-workers demonstrated that simple alcohols can be used for selective C-3-alkylation of indoles. This reaction is based on the so-called “borrowing hydrogen” methodology. Thereby, an alcohol or amine is initially dehydrogenated, then undergoes a functionalization reaction, and finally is rehydrogenated. Applications of this elegant methodology have been developed by the groups of Yus, Fujita, Grigg, Kempe, and us. Based on our ongoing interest in the synthesis of novel indoles and the activation of alcohols, we became interested in the selective N-alkylation of this important class of natural products. At the start of our investigations we studied the reaction of indole with hexanol as a model system. In general, this alkylation might result in N-, C-, and dialACHTUNGTRENNUNGkylated products (Scheme 1).

Selective Ruthenium‐Catalyzed N‐Alkylation of Indoles by Using Alcohols

Synthesis of 3-(Arylsulfonyl)benzothiophenes and Benzoselenophenes via TBHP-Initiated Radical Cyclization of 2-Alkynylthioanisoles or -selenoanisoles with Sulfinic Acids.

The first general examples of palladium-catalyzed direct and selective oxidative C3-acetoxylation of indoles are presented. The mild reaction conditions (70 °C and with weak base, KOAc) in this indole C-H-acetoxylation are notable.

Palladium-Catalyzed Direct and Regioselective C−H Bond Functionalization/Oxidative Acetoxylation of Indoles†

Selective Ruthenium-Catalyzed Alkylation of Indoles by Using Amines

3-Amidoindoles were synthesized from commercially available arylhydrazines and propargylamines over Zn-salt mediated one pot procedure in excellent regioselectivity and up to 94% yield.

A new facile synthesis of 3-amidoindole derivatives and their evaluation as potential GSK-3β inhibitors

The synthesis of new pharmaceutically interesting 3-(2-N,N-diethylaminoethoxy)indole derivatives is described. Starting from 3-silyloxy-2-methylindoles, deprotection and in situ aminoalkylation provided 3-(2-N,N-diethylaminoethoxy)indoles in good yield. Further sulfonylation of these novel indoles gave access to potential 5-HT6 receptor ligands.

Synthesis of 3-(2-N,N-Diethylaminoethoxy)indoles as Potential 5-HT6 Receptor Ligands.

Synthesis of 3-(2-N,N-diethylaminoethoxy)indoles as potential 5-HT6 receptor ligands

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Synthesis of 3-(2-N,N-Diethylaminoethoxy)indoles as Potential 5-HT6 Receptor Ligands.

Synthesis of 3-(2-N,N-diethylaminoethoxy)indoles as potential 5-HT6 receptor ligands