Literature DB >> 10814479

A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride.

T Okauchi1, M Itonaga, T Minami, T Owa, K Kitoh, H Yoshino.   

Abstract

[reaction--see text] Indoles are selectively acylated at the 3-position in high yields on treatment with a wide variety of acyl chlorides in CH(2)Cl(2) in the presence of diethylaluminum chloride or dimethylaluminum chloride. The reaction proceeds under mild conditions and is applicable to indoles bearing various functional groups without NH protection.

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Year:  2000        PMID： 10814479     DOI： 10.1021/ol005841p

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Electrophilic aromatic substitution of a BN indole.

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2.  Total synthesis of the chlorine-containing hapalindoles K, A, and G.

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Journal:  Angew Chem Int Ed Engl       Date:  2011-07-07       Impact factor: 15.336

3.  Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core.

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Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents.

Authors:  Jenny L Wiley; Valerie J Smith; Jianhong Chen; Billy R Martin; John W Huffman
Journal:  Bioorg Med Chem       Date:  2012-01-30       Impact factor: 3.641

5.  Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.

Authors:  Gerardo X Ortiz; Brett N Hemric; Qiu Wang
Journal:  Org Lett       Date:  2017-03-10       Impact factor: 6.005

6.  Structural Elucidation of Metabolites of Synthetic Cannabinoid UR-144 by Cunninghamella elegans Using Nuclear Magnetic Resonance (NMR) Spectroscopy.

Authors:  Shimpei Watanabe; Unnikrishnan Kuzhiumparambil; Shanlin Fu
Journal:  AAPS J       Date:  2018-03-08       Impact factor: 4.009

7.  The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse.

Authors:  Samuel D Banister; Shane M Wilkinson; Mitchell Longworth; Jordyn Stuart; Nadine Apetz; Katrina English; Lance Brooker; Catrin Goebel; David E Hibbs; Michelle Glass; Mark Connor; Iain S McGregor; Michael Kassiou
Journal:  ACS Chem Neurosci       Date:  2013-04-17       Impact factor: 4.418

8.  Acylation of N-p-Toluenesulfonylpyrrole Under Friedel-Crafts Conditions. Evidence for Organoaluminum Intermediates.

Authors:  John W Huffman; Valerie J Smith; Lea W Padgett
Journal:  Tetrahedron       Date:  2008-02-25       Impact factor: 2.457

9.  2,30-Bis(10H-indole) heterocycles: New p53/MDM2/MDMX antagonists.

Authors:  Constantinos G Neochoritis; Kan Wang; Natalia Estrada-Ortiz; Eberhardt Herdtweck; Katarzyna Kubica; Aleksandra Twarda; Krzysztof M Zak; Tad A Holak; Alexander Dömling
Journal:  Bioorg Med Chem Lett       Date:  2015-12-15       Impact factor: 2.823

10.  Data on individual metabolites of synthetic cannabinoids JWH-018, JWH-073 and AM2201 by Cunninghamella elegans.

Authors:  Shimpei Watanabe; Unnikrishnan Kuzhiumparambil; Zophia Winiarski; Shanlin Fu
Journal:  Data Brief       Date:  2016-02-23
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