Oligomerization of<i>N</i>-Tosylindole with Aluminum Chloride

Fujino, Kazutaka; Yanase, Emiko; Shinoda, Yoshihiko; Nakatsuka, Shin‐ichi

doi:10.1271/bbb.68.764

Cited by 8 publications

(1 citation statement)

References 22 publications

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“…Dimer 4 is possibly formed through generation of indolinium cation A by coordination of Sc(OTf) 3 at the C-3 position followed by nucleophilic attack by a second indole at the electrophilic C-2 position of A (Scheme 2). This pathway is consistent with previous reports 14,15 and with the substituent effect observed on the yield. Lower yields were obtained from indoles with electron-withdrawing groups compared with indoles with electron-donating groups.…”

Section: Paper Syn Thesissupporting

confidence: 93%

Sc(OTf)3-Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles

Shelke¹,

Kumar²

2017

Synthesis

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Oligomerization of substituted indoles and N-methylindoles was investigated in the presence of catalytic amounts of scandium triflate in dichloromethane. Two types of indole oligomer, 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles were obtained based on the substituent on indole ring. This study constitutes the first example of Sc(OTf)3-catalyzed oligomerization of indoles and gave good yield of 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles.

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Section: Paper Syn Thesissupporting

confidence: 93%

Sc(OTf)3-Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles

Shelke¹,

Kumar²

2017

Synthesis

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Synthesis of Indole‐Derived Allocolchicine Congeners through Pd‐Catalyzed Intramolecular C‐H Arylation Reaction

et al. 2014

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The synthesis of several new heterocyclic structural analogs of the natural antimitotic agent allocolchicine is reported. As a key step an intramolecular Pd‐catalyzed C–H arylation reaction was used to close the seven‐membered ring fused with two electron‐rich aryl fragments. The stereostructure of the target compounds was determined by X‐ray crystal analysis. The primary biological assessment of the synthesized compounds was carried out on human lymphoma cells. Several allocolchicinoids were determined to possess antiproliferative and apoptosis‐inducing activity in the micromolar concentration range.

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Brønsted acidic ionic liquid–catalyzed tandem trimerization of indoles: An efficient approach towards the synthesis of indole 3,3′‐trimers under solvent‐free conditions

Chatterjee

Santra

Zyryanov

et al. 2020

Journal of Heterocyclic Chem

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We have observed the role of 1-butane sulfonic acid-3-methylimidazolium tosylate, [BSMIM]OTs, as an organocatalyst for the tandem type trimerization of indoles to synthesize indole 3,3 0 -trimers under neat conditions. Using this developed protocol synthesis of indole trimers with various substituted indoles, which are biologically important, has been reported. From the control experiments and literature, a possible mechanism has been proposed via the generation of indolinium cation in the presence of the ionic liquid catalyst. The catalyst has been recycled for several times. The significant advantages of our methodology are clean reaction with very short time, no chromatography for purification, commercially available substrates, neat reaction conditions, and in the absence of metal. Using the protocol, the MDM2-p53 inhibitor has been synthesized in gram scale with high yield.

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Oligomerization ofN-Tosylindole with Aluminum Chloride

Cited by 8 publications

References 22 publications

Sc(OTf)3-Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles

Sc(OTf)3-Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles

Synthesis of Indole‐Derived Allocolchicine Congeners through Pd‐Catalyzed Intramolecular C‐H Arylation Reaction

Brønsted acidic ionic liquid–catalyzed tandem trimerization of indoles: An efficient approach towards the synthesis of indole 3,3′‐trimers under solvent‐free conditions

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