Synthesis of 5-aryl-3,3'-bis-indolyl and bis-7-aza-indolyl methanone derivatives from 5-bromo-7-azaindoles via sequential methylenation using microwave irradiation, CAN oxidation, and Suzuki coupling reactions

A catalyst-free and green chemical method has been developed for the methylenation of indole and -methyl-7-aza indoles with aqueous formaldehyde afforded respective , '-dimethyl-3,3'-bis-7-azaindolylmethanes under microwave irradiation in excellent yield. Subsequent oxidation of the produc...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2022-10, Vol.12 (47), p.30712-30721
Main Authors: Pavithra, Elavarasan, Kannadasan, Sathananthan, Shanmugam, Ponnusamy
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical reactions
Chemistry
Coupling
Fluorescence
Indoles
Irradiation
Oxidation
Oxidizing agents
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A catalyst-free and green chemical method has been developed for the methylenation of indole and -methyl-7-aza indoles with aqueous formaldehyde afforded respective , '-dimethyl-3,3'-bis-7-azaindolylmethanes under microwave irradiation in excellent yield. Subsequent oxidation of the products thus obtained, using one electron chemical oxidant CAN afforded , '-dimethyl-3,3'-bis-7-azaindolylmethanone derivatives in excellent yield. This resulted in methanone derivatives with halogen substitution at the aryl ring which when subjected to Suzuki coupling with aryl boronic acids furnished highly functionalized fluorescent biaryl derivatives. Plausible mechanisms, characterization including XRD, and evaluation of photophysical properties of the Suzuki coupled products are described.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra05849a