Friedel-crafts reaction of activated benzene rings with captodative and electron-deficient alkenes. A one-step synthesis of the natural product methyl 3-(2,4,5-trimethoxyphenyl)propionate

Raúl Aguilar, Adriana Benavides, Joaquín Tamariz

Research output: Contribution to journalArticle

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Abstract

Electrophilic aromatic substitution of activated benzenes with the captodative olefin 1-acetylvinyl-1-p-nitrobenzoate (9), and with the electron-deficient alkenes methyl acrylate (8a), methylvinylketone (8b), and acrolein (8c) were evaluated under Lewis acid catalysis. Olefin 9 proved to be much more reactive than alkenes 8a-8c. We also describe a one-step synthesis of the antifungal and larvicidal natural product methyl 3-(2,4,5-trimethoxyphenyl) propionate (6), by reaction of 1,2,4-trimethoxybenzene with 8a under microwave irradiation.
Original languageAmerican English
Pages (from-to)2719-2735
Number of pages2445
JournalSynthetic Communications
DOIs
StatePublished - 21 Sep 2004

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