LiOBu-promoted synthesis of bis(3-indolyl)methanes by the alkylation of indoles with alcohols under air

Bis(3-indolyl)methanes (BIMs) are known for their important bioactivities, which include anti-cancer, anti-inflammatory, antibacterial, and antioxidant properties. In this study, we are disclosing a metal catalyst-free synthesis of BIMs in high yields via the alkylation reaction of indoles and alcoh...

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Published in:RSC advances 2024-01, Vol.14 (4), p.2341-2345
Main Authors: Nguyen, Hai Yen, Tran, Thu Hue, Do, Ha Nam, Van Do, Dang, Ngo, Quoc-Anh, Tien, Nguyen Quyet, Thanh Nga, Truong Thi, Nguyen, Hien, Hung, Tran Quang, Dang, Tuan Thanh
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Summary:Bis(3-indolyl)methanes (BIMs) are known for their important bioactivities, which include anti-cancer, anti-inflammatory, antibacterial, and antioxidant properties. In this study, we are disclosing a metal catalyst-free synthesis of BIMs in high yields via the alkylation reaction of indoles and alcohols in the presence of lithium tert -butoxide base. Notably, oxygen in air played an important role as an oxidant for the facilitation of this transformation. Interestingly, unactivated aliphatic alcohols could be successfully used as alkylating reagents in the alkylation reactions of indole. Especially, several chemical intermediates detected by GC-MS gave important information about the mechanism insights. This method demonstrated cost and environmental advantages for the development of green processes. Bis(3-indolyl)methanes (BIMs) are known for their important bioactivities, which include anti-cancer, anti-inflammatory, antibacterial, and antioxidant properties.
ISSN:2046-2069
DOI:10.1039/d3ra07115d