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†,10.1039/D2RA05849A

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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†

Elavarasan Pavithra,Sathananthan Kannadasan,Ponnusamy Shanmugam

RSC Advances Pub Date : 10/27/2022 00:00:00 , DOI:10.1039/D2RA05849A

Abstract

A catalyst-free and green chemical method has been developed for the methylenation of indole and N-methyl-7-aza indoles with aqueous formaldehyde afforded respective N,N′-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 N,N′-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.