Semicarbazones and thiosemicarbazones of the heterocyclic series

Tomchin, A. B.; Зеленин, K. Н.; Shirokii, G. A.

doi:10.1007/bf00474095

Cited by 2 publications

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“…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%

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: 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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Semicarbazones and thiosemicarbazones of the heterocyclic series

Cited by 2 publications

References 0 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

Intramolecular Reversible Addition Reactions to the C=O Group

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