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Indoles 3-acylated

Table 15.3 gives some examples of reductive deoxygenation of 2-acyl and 3-acyl indoles. [Pg.151]

ALKYLATED AND 3 ACYLATED INDOLES FROM A COMMON PRECURSOR 3-BENZYLINDOLE AND 3-BENZOYLINDOLE... [Pg.8]

Lithiumalanat reduziert auch 3-Formyl- und 3-Acyl-indole zu den Alkyl-indolen, wenn das Stickstoff-Atom nicht methyliert ist14,15 z.B. ... [Pg.290]

Table 15.3 gives some examples 3-acyl indoles. [Pg.177]

Acylated indoles, in their enol form (54), are formed by heating the phenyliodo-nium ylide of 2-hydroxy-1,4-naphthoquinone in the presence of some indoles.58 The intermediacy of an o ,a ,-dioxoketene (55) is suggested. The same reactants (with the exception of indole itself) form 3-(3-indolyl)-2-hydroxy-1,4-naphthoquinones in a Cu(II)-catalysed reaction. [Pg.177]

Thermal decomposition of phenyliodonium ylide of 2-hydroxy-l,4-naphthoquinone (lawsone) 403 in the presence of indole derivatives 402 (GH2CI2, reflux, 4-7 h) affords 3-acylated indoles existing in their enol forms 404, through a ring contraction and ot,ot -dioxoketene formation reaction (Scheme 87) <2005JOC8780>. [Pg.107]

For a similar reason the carbonyl group of benzopiperi-dones or of 3-acyl-indoles behaves chemically more like an amidic carbonyl then like a ketonic one. hi 2-methoxy-jpflrfl-benzoquinone the reactivity of the methoxy group is... [Pg.287]

The Vilsmeier reaction is a very efficient method for the preparation of 3-formyl-indoles/° and for other 3-acyl-indoles using tertiary amides of other acids in place of dimethylformamide. Even indoles carrying an electron-withdrawing group at the 2-position, for example ethyl indole-2-carboxylate, undergo smooth Vilsmeier 3-formylation. ... [Pg.377]

Acyl-indoles, however, undergo a very selective substitution at C-4, due to chelation and protection of the heterocyclic ring by the electron-withdrawing 3-substituent." The products are good intermediates for the preparation of 4-substimted indoles, for example 4-iodo- and thence 4-aIkoxy-," 4-alkenyl-" and... [Pg.385]

Indolyl A-Grignards, "" or even better their zinc analogues, undergo reaction predominantly at C-3 with a variety of carbon electrophiles such as aldehydes, ketones and acid halides, or reactive halo-hetero-cycles. Including aluminium chloride in the zinc reactions produces high yields of 3-acyl-indoles. The copper-catalysed reactions of indolyl-A-Grignards with A-t-butoxycarbonyl-aziridines also proceed well at C-3. ... [Pg.387]

Acyl-indole reagieren mit Hydrazin-Hydrat zu 4-(2-Amino-phenyl)-1 H-pyrazo-... [Pg.527]

Thallation of 3-acyl indoles gives the 4-thallated products, which can be converted to both the 4-nitro and 4-azido derivatives in copper(II)-promoted processes <89H(29)643>. The nitro compound is formed by heating the organothallium intermediate with sodium nitrite and copper sulfate in DMF at 100°C. This methodology has been used in a total synthesis of indolactam-V <90T6623>. [Pg.43]

Very recently, 2-(2-pyridyl)indoles (130) reacted with nitroolefms (131) to form 3-acyl indoles (132) in up to 98% yields (20 examples) by means of 10 mol% CeCl3-7H20 as the catalyst (2016TL800). The proposed mechanism includes an initial Friedel-Crafts reaction and a subsequent Ce(III)-catalyzed Nef reaction followed by sequential oxidation. [Pg.117]

The acylation of arenes with alcohols has been shown to be possible using a palladium chloride catalyst in the presence of f-butylhydroperoxide. In 2-arylpyridines, substitution is directed to the ortho-position and, after initial paUadation, the formation of intermediate (59) is likely before reductive elimination yields the acylated product. The regioselective acetoxylation of indoles, at the 3-position, has been achieved using the palladium-catalysed reaction with phenyliodonium acetate. 3-Acyl indoles may also be prepared using acetyl chlorides with zirconium tetrachloride as a Lewis acid catalyst. [Pg.271]

Alkynes have been widely employed as the rr-component, with both A -nucleophiles (Scheme 6.46)" and 0-nucleophiles (Scheme 6.47) to give a variety of heterocycles. An application of particular importance has been in the synthesis of indoles 6.142 by the cyclization of o-alkynyl aniline 6.141 derivatives (Scheme 6.48)." The system may be extended to the synthesis of 3-acyl indoles 6.144 by the inclusion... [Pg.207]


See other pages where Indoles 3-acylated is mentioned: [Pg.9]    [Pg.11]    [Pg.13]    [Pg.291]    [Pg.122]    [Pg.371]    [Pg.186]    [Pg.161]    [Pg.85]    [Pg.86]    [Pg.87]    [Pg.245]    [Pg.2458]   
See also in sourсe #XX -- [ Pg.177 ]




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3- Acyl-37/-indoles

3-Acylation, of indoles

Acylated indole synthesis, aluminum chloride

Acylation of indole

Acylation, ionic liquids acylated indoles

Anilides 9-acyl, indoles from

Carboxylic acids indoles, 1-acyl

Indole 3-acylation

Indole 3-acylation

Indole derivatives 1- acylation

Indole, 3-acyl

Indole, 3-acyl

Indoles 3- -. intramolecular 4-acylation

Indoles 3-acyl- from

Indoles Friedel-Crafts acylation

Indoles acylation

Indoles benzene-ring acylation

Indoles, 3-acyl-, Wolff-Kishner reduction

N-Acyl indoles

Vilsmeier-Haack formylation/acylation indoles

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