The indophenine reaction revisited. Properties of a soluble dialkyl derivative

Tormos, Gregory V.; Belmore, Kenneth A.; Cava, Michael P.

doi:10.1021/ja00077a057

Cited by 49 publications

(69 citation statements)

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“…These compounds are formed as a mixture of geometric isomers 448 , and may possess one or two thiophene units; the latter being the major product 449 (Scheme 111).…”

Section: Scheme 110mentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

848

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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“…These compounds are formed as a mixture of geometric isomers 448 , and may possess one or two thiophene units; the latter being the major product 449 (Scheme 111).…”

Section: Scheme 110mentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

848

447

View full text Add to dashboard Cite

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“…For example, oxidative cleavage of tagged oxindoles 7 and 8, FSPE and condensation with 1,2-phenyldiamine, gave 54 and 55, [27] while fluorination with diethylaminosulfur trifluoride (DAST) gave difluorooxindoles [28] 56 and 57 (Scheme 5). Similarly, after cleavage of the tag from 8 and FSPE, treatment of the crude indoline-1,2-dione with varying amounts of 2-thienyllithium led to the corresponding mono-and bisaddition products, [29] 58 and 59 (Scheme 6). Finally, a Bucherer-Bergs reaction [30] was used to convert the crude indoline-1,2-dione to spirohydantoin 60.…”

Section: Introductionmentioning

confidence: 99%

A Fluorous, Pummerer Cyclative‐Capture Strategy for the Synthesis of N‐Heterocycles

McAllister

McCormick

James

et al. 2007

Chemistry A European J

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A fluorous, cyclative-capture strategy based on a new Pummerer cyclization process allows rapid access to tagged, heterocyclic frameworks. Convenient modification of the fluorous, heterocyclic scaffolds by using a variety of approaches including Pd-catalyzed cross-couplings is possible. Traceless, reductive cleavage of the fluorous-phase tag or oxidative cleavage and further elaboration, completes a strategy for the high-throughput, fluorous-phase synthesis of a diverse range of N-heterocycles.

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“…Similarly, after cleavage of 8 and FSPE, treatment of the crude indoline-1,2-dione with varying amounts of 2-thienyllithium led to the corresponding mono-and bis-addition products [15], 23 and 24 (Scheme 5). Finally, a Bucherer -Bergs reaction [16] was used to convert the crude indoline-1,2-dione 9 to spirohydantoin 25 (Scheme 5).…”

Section: Resultsmentioning

confidence: 99%