A new approach for one-pot, green synthesis of new polycyclic indoles in aqueous solution

Ameri, Mohsen; Asghari, Alireza; Amoozadeh, Ali; Bakherad, Mohammad

doi:10.1016/j.cclet.2016.11.022

Cited by 6 publications

(2 citation statements)

References 16 publications

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“…Asghari and co‐workers reported an efficient synthesis of polycyclic indole derivatives 53 via the electrooxidation reaction of phenylamines 48 with pyrazolidine‐3,5‐dione 50 as the nucleophile in a phosphate buffer solution mixed with ethanol (Scheme ) . Their study indicated that the oxidized form of the phenylamines ( 49 ) participated in a double Michael addition with the pyrazolidine‐3,5‐dione 50 (or as its enol form 51 ) finally leading to the formation of polycyclic indoles 53 .…”

Section: Electrochemical Synthesis Of Indole Derivativesmentioning

confidence: 99%

Recent Advances in the Electrochemical Synthesis and Functionalization of Indole Derivatives

Zhong

et al. 2020

Adv Synth Catal

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The chemists’ pursuit of the ideal synthesis and functionalization of indole derivatives has lasted over 150 years as their scaffolds have been widely found in natural products, pharmaceuticals, agrochemicals and organic materials. In this regard, the recent resurgence of adopting green and sustainable electrochemistry in organic synthesis suggests that electrosynthesis is a promising strategy. Indeed, many new intriguing applications of synthesis and functionalization of indole derivatives by direct and redox‐mediated electrochemical means have been disclosed. In this review, we highlight the fundamental aspects, reaction scopes, synthetic applications and reaction mechanisms of the electrochemical synthesis and functionalization of indole derivatives.

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Section: Electrochemical Synthesis Of Indole Derivativesmentioning

confidence: 99%

Recent Advances in the Electrochemical Synthesis and Functionalization of Indole Derivatives

Zhong

et al. 2020

Adv Synth Catal

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“…38 In 2017, the Asghari group reported an electrochemical synthesis of polycyclic indoles from phenylamines with pyrazolidine-3,5-dione in a mixture of phosphate buffer solution and ethanol (Scheme 18). 39 In this reaction, the anodic oxidation of phenylamine 106 generates intermediate 109, which reacts with pyrazolidine-3,5-dione 107 or its enol form 107 0 to give intermediate 110. Intermediate 110 can be further oxidized at the anode to produce 111, which then reacts with the second molecule of 107 0 to afford intermediate 112.…”

Section: Electrochemical Intermolecular Annulationmentioning

confidence: 99%

Recent advances in electrochemically enabled construction of indoles from non-indole-based substrates

Zheng,

Chen,

et al. 2024

Chem. Commun.

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Electrochemical [3+2] Cycloaddition of Anilines and 1,3‐Dicarbonyl Compounds: Construction of Multisubstituted Indoles

Chang

Chen

et al. 2022

Adv Synth Catal

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Indoles, especially multisubstituted ones, are privileged scaffolds found widely in natural products, bioactive molecules, fine chemicals, and organic functional materials. Although several intramolecular electrochemical cyclization reactions of vinyl anilines to construct indoles have been reported in recent years, the intermolecular process between simple anilines and other readily available synthons, even though dominant, remains relatively unexplored. Herein, we report the intermolecular electro-oxidative cycloaddition of anilines and commercially available 1,3-dicarbonyl compounds. This method provides an alternative route for the synthesis of a broad range of multisubstituted indoles without a transition-metal catalyst or external chemical oxidant.

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A new approach for one-pot, green synthesis of new polycyclic indoles in aqueous solution

Cited by 6 publications

References 16 publications

Recent Advances in the Electrochemical Synthesis and Functionalization of Indole Derivatives

Recent Advances in the Electrochemical Synthesis and Functionalization of Indole Derivatives

Recent advances in electrochemically enabled construction of indoles from non-indole-based substrates

Electrochemical [3+2] Cycloaddition of Anilines and 1,3‐Dicarbonyl Compounds: Construction of Multisubstituted Indoles

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