4.5 Article

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

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SYMMETRY-BASEL
卷 14, 期 3, 页码 -

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MDPI
DOI: 10.3390/sym14030435

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indoles; C-H activation; Pd-catalyzed coupling; microwave irradiation; N-aryl enamines

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  1. [823939]

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We report an efficient procedure for the synthesis of functionalized indole derivatives, which is an important framework in natural products and pharmaceuticals. The synthesized compounds showed excellent yields and high regioselectivity, and were confirmed by spectroscopic analysis.
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 palladium-catalyzed 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 H-1 and C-13 spectroscopic means as well as by high-resolution mass spectrometry.

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