Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes with the Cyanate Ion: Access to Spiro[pyrrolidone-3,3′-oxindoles]

Zaytsev, Sergey V.; Ivanov, Konstantin L.; Skvortsov, Dmitry A.; Bezzubov, Stanislav I.; Melnikov, M.Y.; Будынина, Екатерина М.

doi:10.1021/acs.joc.8b00922

Cited by 30 publications

(14 citation statements)

References 52 publications

(48 reference statements)

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“…Diethyl-(1S,3R)-1′-benzyl-3-(3-methyl-4-nitroisoxazol-5-yl)-2′oxospiro[cyclopropane-1,3′-indoline]-2,2-dicarboxylate (5). Light yellowish oil, 24% yield (25.1 mg).…”

Section: ′-(Tert-butyl)-22-diethyl-(1s3r)-7′-fluoro-3-(3-methyl-4-nit...mentioning

confidence: 99%

Asymmetric Synthesis of Spiro-3,3′-cyclopropyl Oxindoles via Vinylogous Michael Initiated Ring Closure Reaction

2022

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A novel organocatalytic cascade approach for the synthesis of spiro-cyclopropyl oxindole derivatives has been developed. The methodology is based on asymmetric vinylogous Michael addition of 4-nitroisoxazole derivatives to N-Boc isatylidene malonates followed by intramolecular alkylation. Its remarkable stereocontrol, wide substrate scope, and scalability highlight this new developed strategy. Moreover, this work represents the first example of vinylogous Michael initiated ring closure (MIRC) reaction for the synthesis of chiral 3,3′-cyclopropyl oxindole.

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“…Diethyl-(1S,3R)-1′-benzyl-3-(3-methyl-4-nitroisoxazol-5-yl)-2′oxospiro[cyclopropane-1,3′-indoline]-2,2-dicarboxylate (5). Light yellowish oil, 24% yield (25.1 mg).…”

Section: ′-(Tert-butyl)-22-diethyl-(1s3r)-7′-fluoro-3-(3-methyl-4-nit...mentioning

confidence: 99%

Asymmetric Synthesis of Spiro-3,3′-cyclopropyl Oxindoles via Vinylogous Michael Initiated Ring Closure Reaction

2022

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“…reported the nucleophilic ring‐opening of the cyclopropane ring with cyanate ion, which is isoelectronic to azide ion. They have described the microwave‐assisted nucleophilic ring‐opening of DACs 18 , spiro‐activated with an oxindole fragment as acceptors, by cyanate ion . This method provides a facile access to biologically important spiro[pyrrolidone‐3,3′‐oxindole] derivatives 19 (Scheme ).…”

Section: Synthesis Of Five‐membered Nitrogen Heterocyclesmentioning

confidence: 99%

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

et al. 2020

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Nitrogen‐containing molecules are the key structural constituent of many pharmaceutical compounds that play a pivotal role in drug development. Owing to their multifaceted medicinal importance, several synthetic approaches have been delineated in the recent past for their construction. Over the past few decades the augmented use of donor–acceptor cyclopropanes (DACs) as three‐carbon synthetic equivalents, despite their ring strain, for the construction of innumerable hetero‐ and carbocycles of pharmaceutical importance has raised the interest of synthetic chemists to this topic. Owing to their zwitterionic nature due to the vicinal disposition of donor and acceptor groups, they have been frequently used in ring‐opening reactions, cycloadditions, and rearrangements. This review is mainly focused on assorted reactions of DACs with various nitrogen‐containing dipolarophiles like imines, azides, cyanates, isothiocyanates, nitrosocarbonyls, hydrazines, diaziridines, triazinanes, diazenes, etc. towards the synthesis of nitrogen‐containing molecules of pharmaceutical and industrial importance. This review is in continuation of our review published in the Israel Journal of Chemistry in April 2016, and includes the literature from April 2016 to May 2019.

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“…Similarly, these derivatives displayed significant cytotoxicity profile on HEK293T cancer cell lines with IC 50 value of 6.8 ± 0.7 µ m . [ 66 ]…”

Section: Reactions Of Spirocyclopropyl Oxindolesmentioning

confidence: 99%

Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review

2020

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Spirocyclopropyl oxindole represents an emerging framework by unique amalgamation of versatile 2‐oxindole motif and highly strained cyclopropane unit. This scaffold is remarkable for its diverse medicinal and synthetic applications. The present review delivers a comprehensive overview of the strategies to afford spirocyclopropyl oxindoles and their potential synthetic transformations. The syntheses of spirocyclopropyl oxindoles have been described based on the type of precursors, including isatin, 3‐alkenyl oxindole, diazooxindole, oxindole, and 3‐chlorooxindole. Besides, the utility of different cyclopropanation reagents like sulfur ylide, MBH‐carbonate, carbenoid, vinyl selenone, etc. have also been emphasized. Furthermore, various ring‐expansion/opening reactions of spirocyclopropane oxindoles using dipolarophiles/nucleophiles have critically been illustrated.

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Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes with the Cyanate Ion: Access to Spiro[pyrrolidone-3,3′-oxindoles]

Cited by 30 publications

References 52 publications

Asymmetric Synthesis of Spiro-3,3′-cyclopropyl Oxindoles via Vinylogous Michael Initiated Ring Closure Reaction

Asymmetric Synthesis of Spiro-3,3′-cyclopropyl Oxindoles via Vinylogous Michael Initiated Ring Closure Reaction

Donor–Acceptor Cyclopropanes as an Expedient Building Block Towards the Construction of Nitrogen‐Containing Molecules: An Update

Syntheses and Applications of Spirocyclopropyl Oxindoles: A Decade Review

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