Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst

Thanh, Nga Phan Thi; Thu, Huong Dang Thi; Tone, Masaya; Inoue, Hisahiro; Iwasa, Seiji

doi:10.1016/j.tet.2020.131481

Cited by 5 publications

(4 citation statements)

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“…45 They have primarily been applied to a number of cycloaddition reactions and O-H insertions, [45][46][47][48][49][50][51][52][53][54] however, there are very few reports of their application to C-H insertions, despite a number of attempts principally by Yang and Xu and coworkers. [55][56][57][58] In a recent study, Yang and Xu investigated if aliphatic sp 3 C-H insertions were possible with a range of ester, methyl ketone and benzoyl substituted α-diazo-β-keto sulfonamides with rhodium and copper catalysts, however, 1,4-, 1,5-, or 1,6-C(sp 3 )-H insertion was not realised across a wide range of derivatives (Scheme 3, A). [55][56][57] Instead, only aromatic insertion into the 1,5-C(sp 2 )-H bond to form the corresponding benzo-γ-sultam proved possible.…”

Section: Scheme 2 Previous Work Within the Maguire Groupmentioning

confidence: 99%

“…Iwasa's group described a similar aromatic insertion using an -diazosulfonamide to form a sultam in a study focused on the generation of oxindoles from -diazoamides under rhodium catalysis. 58…”

Section: Scheme 1 Previous Work By Mckerveymentioning

confidence: 99%

“…-Diazo--keto sulfonamides 1a-d and 1f were synthesised in order to investigate if aliphatic C-H insertion occurs in situations where the -diazo--keto sulfonamide bears an aryl ketone and two alkyl substituents on the nitrogen, which had not been previously explored. [55][56][57][58] -Diazo--keto sulfonamides 1e, 1g, and 1h without an extend-ed alkyl chain on the nitrogen, which could lead to sultam formation, were synthesised for comparison.…”

Section: Paper Synthesismentioning

confidence: 99%

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Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides

Collins,

Maguire,

Judge

et al. 2024

Synthesis

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Copper mediated reactions of α-diazo-β-keto sulfonamides 1 leads to a range of products including the alkyne sulfonamides 5, the enamines 6, and the α-halosulfonamides 7 and 11 with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-keto sulfones. Use of copper(II) triflate (5 mol%) led to isolation of a series of alkyne sulfonamides 5 (up to 12%) and enamines 6 (up to 64%). Use of copper(II) chloride (5 mol%) formed, in addition, the α-halosulfonamides 7; use of stoichiometric amounts of copper(II) chloride/bromide enables facile halogenation of the β-keto sulfonamide to form the α-halosulfonamides 7 and 11 (up to 63%).

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Section: Scheme 2 Previous Work Within the Maguire Groupmentioning

confidence: 99%

Section: Scheme 1 Previous Work By Mckerveymentioning

confidence: 99%

Section: Paper Synthesismentioning

confidence: 99%

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Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides

Collins,

Maguire,

Judge

et al. 2024

Synthesis

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“…Synthesis of isatin derivatives compounds has been carried out in various ways, including using catalysts. Some catalysts that have been used in the synthesis of isatin derivatives are palladium [16], Ru(II)-Pheo [17], dirhodium(II) [18], and boron trifluoride [19]. Using a catalyst in the organic synthesis reaction gives significantly higher product yields and a shorter time than without a catalyst [20].…”

Section: ■ Introductionmentioning

confidence: 99%

Iodine-catalyzed Synthesis, Antibacterial, and Antioxidant Activity of Isatin Derivatives

Cahyana,

Liandi,

Ongkowidjawa

2024

Indones. J. Chem.

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Isatin is a unique compound with many bioactivities such as antiviral, anti-HIV, antitumor, anti-inflammatory, anticonvulsant, and antifungal. In this study, isatin derivatives were synthesized with an iodine catalyst and tested for antibacterial and antioxidant activities. Isatin derivatives were conducted through a Knoevenagel condensation reaction between isatin and malononitrile. The products were confirmed by thin-layer chromatography, melting point apparatus, FTIR, UV-vis spectroscopy, and LC-MS. The optimum reaction conditions were obtained at 10% mol of catalyst, at boiling point ethanol solvent for 30 min. The yield of the isatin derivative products was 71% (3a), 61% (3b), and 67% (3c). The antibacterial activities of the synthesized compounds were weak activity against S. aureus and E. coli. The antioxidant activity test resulted in IC50 values of 266.47, 220.43, and 654.85 ppm for compounds 3a, 3b, and 3c, respectively. The synthesis method using an iodine catalyst in this reaction offers a higher product yield compared to a catalyst-free reaction.

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Ruthenium Catalyzed Intramolecular C−X (X=C, N, O, S) Bond Formation via C−H Functionalization: An Overview

Singh

Chouhan

Mukherjee

2021

Chemistry An Asian Journal

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Ruthenium catalyzed C−H activation is well known for its high tolerance towards the functional group and broad applicability in organic synthesis and molecular sciences, with significant applications in pharmaceutical industries, material sciences, and polymer industry. In the last few decades, enormous progress has been observed with ruthenium‐catalyzed C−H activation chemistry. Notably, the vast majority of the C−H functionalization known in the literature are intermolecular, although the intramolecular variant provides fascinating new structural facet starting from the simple molecular scaffolds. Intramolecular C−H functionalization is atom economical and step efficient, results in less formation of undesired products which is easy to purify. This has created a lot of interest in organic chemistry in developing new synthetic strategies for such functionalization. The focus of this review is to present the relatively unexplored intramolecular functionalization of C−H bonds into C−X (X=C, N, O, S) bonds utilizing versatile ruthenium catalysts, their scope, and brief mechanistic discussion.

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Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst

Cited by 5 publications

References 58 publications

Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides

Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides

Iodine-catalyzed Synthesis, Antibacterial, and Antioxidant Activity of Isatin Derivatives

Ruthenium Catalyzed Intramolecular C−X (X=C, N, O, S) Bond Formation via C−H Functionalization: An Overview

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