The synthesis of indole-3-carbinols (I3C) and their application to access unsymmetrical bis(3-indolyl)methanes (BIMs) bearing a quaternary sp-carbon

In the present study, the novel synthesis of tert -indole-3-carbinols is reported through the DDQ-mediated oxidation of the allylic C-H bond/aromatization/hydroxylation at the indolyl carbon using water as the hydroxyl source. The reaction is highly efficient and high yielding and it works under mil...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 2; no. 26; pp. 5234 - 5238
Main Authors Kundal, Sandip, Rana, Gopal, Kar, Abhishek, Jana, Umasish
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 06.07.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RECENT PROGRESS
DERIVATIVES
SIMPLE INDOLE ALKALOIDS
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Summary:In the present study, the novel synthesis of tert -indole-3-carbinols is reported through the DDQ-mediated oxidation of the allylic C-H bond/aromatization/hydroxylation at the indolyl carbon using water as the hydroxyl source. The reaction is highly efficient and high yielding and it works under mild reaction conditions. Furthermore, the synthetic value of such indole-based tert -carbinols is explored through their use as excellent electrophilic methylene surrogates to develop medicinally important unsymmetrical bis(3-indolyl)methanes containing an all carbon quaternary center. A novel DDQ/H 2 O-mediated synthetic method is developed for tert -indole-3-carbinols, and their application in the synthesis of unsymmetrical bis(3-indolyl)methanes with all-carbon quaternary centres is described.
Bibliography:2156650
For ESI and crystallographic data in CIF or other electronic format see DOI
Electronic supplementary information (ESI) available. CCDC No.
https://doi.org/10.1039/d2ob00502f
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00502f