FeCl3 catalyzed intermolecular reaction between enol ethers and anilines: Access to 2,3-substituted indoles through aryl group migration

Jena, Tapan Kumar; Khan, Faiz Ahmed

doi:10.1016/j.tetlet.2020.152583

Cited by 5 publications

(8 citation statements)

References 40 publications

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“…Recently, Our group introduced a new methodology for the synthesis of thiazolines 130 , dihydrothiazole 131 , and thioureas or enureas 132 derivatives from methyl enol ethers 25 with thiourea or urea 127 – 129 in the presence of trifluoroacetic acid (TFA) at 40–50 °C with good yields (Scheme 43). [66] This metal‐free protocol shows the C−N and C−S bond formation in one‐step. Furthermore, this strategy applied for marine natural product synthesis of wilsoniamine B.…”

Section: Reactions Of Alkyl Enol Ethersmentioning

confidence: 98%

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Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Ahmad

Jena

Khan

2021

Chemistry An Asian Journal

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Alkyl enol ethers (AEE) are versatile synthetic intermediates with a unique reactivity pattern. This review article summarizes the synthesis of AEE as well as its reactivity and how enol ether undergoes intermolecular reactions for various bond formation, leading to the construction of several useful organic molecules. The synthetic applications of alkyl enol ethers towards intermolecular bond‐forming reactions include metal‐catalyzed reactions, cycloaddition and heterocycle formation as well as rwactions in the field of natural products synthesis. The achievement of these impressive transformations prove the countless synthetic potential of AEE. The main objective of this review is to bring attentiveness among synthetic chemists to show how AEE extensively can be used to react with both electrophiles as well as nucleophiles, thereby behaving as an ambiphilic reactant. We trust that the unique reactivity pattern of alkyl enol ethers and the fundamental mechanistic idea can attract chemists in AEE chemistry. Exclusively, intermolecular reactions of AEE with other functionalized moieties have not been reviewed to the best of our knowledge.

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Section: Reactions Of Alkyl Enol Ethersmentioning

confidence: 98%

“…In that reported method we have disclosed a very interesting plausible reaction mechanism where C‐nucleophile followed by N‐nucleophile of aniline attack at the α and β position of methyl enol ether simultaneously, through anchimeric assistance leads to aryl migration (Scheme 52). [74b] …”

Section: Reactions Of Alkyl Enol Ethersmentioning

confidence: 99%

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Ahmad

Jena

Khan

2021

Chemistry An Asian Journal

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“…Spectral data are consistent with those previously reported for this compound. (45) 1 H NMR (700 MHz, CDCl3): 7.98-7.87 (s, 1H),…”

Section: -Fluoro-2-methyl-3-(4-methoxyphenyl)indole (8h)mentioning

confidence: 99%

Use of Vinyl Sulfides in Fischer Indole Reactions

Pal¹,

Fragis²,

Dharavath³

et al. 2022

Synthesis

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Vinyl sulfides accessed via Wittig olefination with thioalkylphosphonium salts are used as aldehyde- or ketone surrogates in Fischer indole reactions. These vinyl sulfides react with arylhydrazines in the presence of TsOH·H2O in refluxing ethanol or dichloroethane to yield diverse 3-substituted and 2,3-disubstituted indoles or azaindoles. The utility of this chemistry is highlighted with the efficient preparation of three biomedically relevant compounds: 4-aza-melatonin, a furoindoline, and an indomethacin-like CRTh2 antagonist.

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“…Recently, our group reported a direct α‐benzylation method using methyl enol ethers leading to synthesis of (±)‐tetrahydronyasol, propterol‐A natural products [14] . Also, new strategies for the synthesis of indole, thiazole and thiazoline derivatives from MEE have been disclosed [15,16] . Ongoing research on diverse reactivity of MEE in our laboratory promoted us to investigate reactions of MEE with a nucleophilic partner.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Transition‐Metal‐Free Synthesis of Polysubstituted Fused Benzene Derivatives from Methyl Enol Ethers and Alkynes

Ahmad

Khan

2022

ChemistrySelect

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A mild and transition‐metal‐free one‐pot strategy is established to prepare polysubstituted naphthalene and phenanthrene derivatives from methyl enol ethers (MEE) with alkynes. Significantly, this protocol is promoted by boron trifluoride diethyl etherate (BF3⋅Et2O) at room temperature. A wide variety of diversely functionalized naphthalene and phenanthrene derivatives were obtained in good to excellent yields. A plausible mechanism involving a spiro quinonoid intermediate is proposed. Due to fluorescent nature of naphthalene, selected compounds were screened for the solvatochromism study. Notably, positive solvatochromism effect was observed in the case of nitro‐substituted naphthalene derivative (3 h) with respect to different polarity of solvents.

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FeCl3 catalyzed intermolecular reaction between enol ethers and anilines: Access to 2,3-substituted indoles through aryl group migration

Cited by 5 publications

References 40 publications

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Use of Vinyl Sulfides in Fischer Indole Reactions

One‐Pot Transition‐Metal‐Free Synthesis of Polysubstituted Fused Benzene Derivatives from Methyl Enol Ethers and Alkynes

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