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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Autores principales: Pillaiyar, Thanigaimalai, Sedaghati, Masoud, B. Mahardhika, Andhika, L. Wendt, Lukas, E. Müller, Christa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8218542/
https://www.ncbi.nlm.nih.gov/pubmed/34221175
http://dx.doi.org/10.3762/bjoc.17.102
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author Pillaiyar, Thanigaimalai
Sedaghati, Masoud
B. Mahardhika, Andhika
L. Wendt, Lukas
E. Müller, Christa
author_facet Pillaiyar, Thanigaimalai
Sedaghati, Masoud
B. Mahardhika, Andhika
L. Wendt, Lukas
E. Müller, Christa
author_sort Pillaiyar, Thanigaimalai
collection PubMed
description 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.
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spelling pubmed-82185422021-07-02 Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center Pillaiyar, Thanigaimalai Sedaghati, Masoud B. Mahardhika, Andhika L. Wendt, Lukas E. Müller, Christa Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2021-06-18 /pmc/articles/PMC8218542/ /pubmed/34221175 http://dx.doi.org/10.3762/bjoc.17.102 Text en Copyright © 2021, Pillaiyar et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Pillaiyar, Thanigaimalai
Sedaghati, Masoud
B. Mahardhika, Andhika
L. Wendt, Lukas
E. Müller, Christa
Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center
title Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center
title_full Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center
title_fullStr Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center
title_full_unstemmed Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center
title_short Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center
title_sort iodine-catalyzed electrophilic substitution of indoles: synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8218542/
https://www.ncbi.nlm.nih.gov/pubmed/34221175
http://dx.doi.org/10.3762/bjoc.17.102
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