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

ABSTRACT: 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.

SUBMITTER: Nguyen HY

PROVIDER: S-EPMC10782282 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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

Nguyen Hai Yen HY Tran Thu Hue TH Do Ha Nam HN Van Do Dang D Ngo Quoc-Anh QA Tien Nguyen Quyet NQ Thanh Nga Truong Thi TT Nguyen Hien H Hung Tran Quang TQ Dang Tuan Thanh TT

RSC advances 20240111 4

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 a ...[more]

PMID: 38213964

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