Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

A novel, versatile approach for the synthesis of unsymmetrical 3,3'-diindolylmethanes (DIMs) with a quaternary carbon center has been developed via iodine-catalyzed coupling of trifluoromethyl(indolyl)phenylmethanols with indoles. In contrast to previously reported methods, the new procedure is...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2021, Vol.17 (1), p.1464-1475
Main Authors: Pillaiyar, Thanigaimalai, Sedaghati, Masoud, B Mahardhika, Andhika, L Wendt, Lukas, E Müller, Christa
Format: Article
Language:English
Subjects:
Acids
alkylation of indole
anti-inflammatory
binding affinity
Cancer
Cannabinoid receptors
Cannabinoids
Carbon
Chemistry
diindolylmethane
Full Research Paper
Iodine
Neurodegenerative diseases
Solvents
Therapeutic targets
unsymmetrical 3,3'-diindolylmethane
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Summary:A novel, versatile approach for the synthesis of unsymmetrical 3,3'-diindolylmethanes (DIMs) with a quaternary carbon center has been developed via iodine-catalyzed coupling of trifluoromethyl(indolyl)phenylmethanols with indoles. In contrast to previously reported methods, the new procedure is characterized by chemoselectivity, mild conditions, high yields, and scalability to obtain gram amounts for biological studies. Selected compounds were found to display affinity for cannabinoid receptors, which are promising drug targets for the treatment of inflammatory and neurodegenerative diseases.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.17.102