Indole moiety is well-known as a superlative framework in many natural products and synthetic pharmaceuticals. Herein, we report an efficient procedure to synthesize a series of functionalized 2-methyl-1H-indole-3-carboxylate derivatives from commercially available anilines properly functionalized by different electron-withdrawing and -donating groups through a palladiumcatalyzed intramolecular oxidative coupling. The conversion of a variety of enamines into the relevant indole was optimized by exposing the neat mixture of reactants to microwave irradiation, obtaining the desired products in excellent yields and high regioselectivity. The synthesized compounds were confirmed by 1H and 13C spectroscopic means as well as by high-resolution mass spectrometry.

Microwave-Assisted Synthesis of 2-Methyl-1H-indole-3-carboxylate Derivatives via Pd-Catalyzed Heterocyclization

Rosa Bellavita
Co-primo
;
Marcello Casertano
Co-primo
;
Nicola Grasso
Secondo
;
Marialuisa Menna;Francesco Merlino
Penultimo
;
Paolo Grieco
Ultimo
2022

Abstract

Indole moiety is well-known as a superlative framework in many natural products and synthetic pharmaceuticals. Herein, we report an efficient procedure to synthesize a series of functionalized 2-methyl-1H-indole-3-carboxylate derivatives from commercially available anilines properly functionalized by different electron-withdrawing and -donating groups through a palladiumcatalyzed intramolecular oxidative coupling. The conversion of a variety of enamines into the relevant indole was optimized by exposing the neat mixture of reactants to microwave irradiation, obtaining the desired products in excellent yields and high regioselectivity. The synthesized compounds were confirmed by 1H and 13C spectroscopic means as well as by high-resolution mass spectrometry.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11588/891063
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