Solution phase synthesis of a spiro[pyrrolidine-2,3′-oxindole] library via a three component 1,3-dipolar cycloaddition reaction

Fokas, Demosthenes; Ryan, William J.; Casebier, David S.; Coffen, David L.

doi:10.1016/s0040-4039(98)00234-2

Cited by 92 publications

(32 citation statements)

References 9 publications

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“…In the 1990s, Grigg et al reported on similar reactions by using proline and other α-amino acids as azomethine ylides precursors and methyl acrylate and α, β-unsaturated ketones as dipolarophiles forming spiro-pyrrolidine-oxindoles [71][72][73]. Recently, this substantial method has found many applications in combinatorial chemistry due its simplicity and variability [74,75].…”

Section: The Reaction Of 13-dipolar Cycloaddition With Azomethine Ylmentioning

confidence: 99%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

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Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications. This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work. The spirooxindoles in this review are separated into three structural classes, and then further categorized into the method type from which the spirocycle is generated.

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Section: The Reaction Of 13-dipolar Cycloaddition With Azomethine Ylmentioning

confidence: 99%

Molecular diversity of spirooxindoles. Synthesis and biological activity

et al. 2015

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“…The reaction of an unstable azomethine ylide and a chiral oxoindolin-3-ylidene acetate ester resulted in an asymmetric synthesis of the oxindole alkaloid horsfiline 291 . This reaction has also been employed in the construction of a molecular library of spiro[pyrrolidine-2,3'-oxindoles] from isatin, aminoacids and chalcones 292,293 (Scheme 70).…”

Section: Scheme 68mentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

847

447

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Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

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“…Several researchers have reported 1,3-dipolar cycloaddition reactions giving the regioisomers, and some have tried to explain the reasons by use of theoretical methods [7,8]. It is a common view that the azomethine ylide is initially generated in situ, via decarboxylative condensation of ninhydrin with proline, and is then trapped by the alkene to construct a new five-membered ring [9].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and regiochemistry of spiro indane-1,3-dione compounds

Chen

Zhang

2011

Res Chem Intermed

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Spiro indane-1,3-dione compounds have been synthesized by 1,3-dipolar cycloaddition of ninhydrin, L-proline, and an alkene (either a chalcone or an (E)-b-arylnitrostyrene). All these reactions proceed with good yield and with high regioselectivity and stereoselectivity. The structures were studied by NMR spectroscopy, MS, and X-ray diffraction analysis. It was found that these two kinds of alkene lead to different regioselectivity. This study has provided information about the regioselectivity of 1,3-dipolar cycloaddition reactions: regioselectivity may be controlled by p-p stacking state; the order of stability of stacking of the Ar and EWG part with the indane-1,3-dione part is: benzoyl group [ phenyl group [ nitro group.

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Solution phase synthesis of a spiro[pyrrolidine-2,3′-oxindole] library via a three component 1,3-dipolar cycloaddition reaction

Cited by 92 publications

References 9 publications

Molecular diversity of spirooxindoles. Synthesis and biological activity

Molecular diversity of spirooxindoles. Synthesis and biological activity

The chemistry of isatins: a review from 1975 to 1999

Synthesis and regiochemistry of spiro indane-1,3-dione compounds

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