ChemInform Abstract: STRUKTUR VON ISATIN‐ALPHA‐THIOSEMICARBAZONEN

Tomchin, A. B.; Shirokii, G. A.

doi:10.1002/chin.197507107

Cited by 3 publications

(4 citation statements)

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“…O-Methylisatin is described as the product of the reaction of methyl iodide with the silver salt of isatin, which can be prepared from isatin and silver acetate 91 . The alkoxy group has been reported to be displaced by nucleophiles such as hydrazines 92 .…”

Section: N-alkylationmentioning

confidence: 99%

“…Tomchin and coworkers also described that Omethylisatin reacts with thiosemicarbazine to furnish isatin-2-thiosemicarbazone, which can undergo a cyclization reaction under acidic conditions to furnish a thiadiazanoindole derivative 92 ; the kinetics of the reaction were subsequently determined 278 . Later, Tomchin also described that isatin-2-thiosemicarbazones suffer a cleavage reaction of the five member ring, and that the intermediate formed recyclizes to a thiadiazole derivative 279 (Scheme 61).…”

Section: Scheme 59mentioning

confidence: 99%

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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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Section: N-alkylationmentioning

confidence: 99%

Section: Scheme 59mentioning

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

show abstract

“…In acidic aqueous solution O'-thiosemicarbazones, dithiocarboxyhydrazones, and thiobenzoylhydrazones of isatin are in equilibrium with 9b-hydroxy-l,3,4-thiadiazino [5,6-b]indoles (242A) ~ (242B) [693,694]. Increasing medium acidity displaces the equilibrium toward the cyclic (242B) which apparently is more basic.…”

Section: Mercapto Aldehydes and Ketones And Related Compoundsmentioning

confidence: 99%

Intramolecular Reversible Addition Reactions to the C=O Group

Valters¹,

Flitsch

1985

Ring-Chain Tautomerism

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“…3 In a similar manner, isatin-3hydrazone has been studied for the colourimetric determination of steroids 4 and in steroid analysis, as well as a colour marker in the Sephadex LH-20 chromatographic separation of steroidal blood components. 5 Further, isatin has been used for the synthesis of fused indole derivatives, such as indolothiazoles, 6 thiadiazinoindoles, 7 pyrazinoindoles, 8 trisindolobenzenes, 9 indoloquinazolines, 10 and 1,2,4-triazinoindole derivatives. [11][12][13][14][15] Isatin derivatives can suffer nucleophilic attack at positions C-2 and/or C-3.…”

mentioning

confidence: 99%