Selective Photo-Reduction of 1-Alkylisatins in Degassed Alcoholic Solutions

Tatsugi, Jiro; Ikuma, Kenji; Izawa, Yasuji

doi:10.3987/com-95-7272

Cited by 20 publications

(12 citation statements)

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“…These derivatives are commonly synthesized from the reaction of the sodium salt of isatin with alkyl halides or sulphates 72,73 . Various methods for the preparation of this salt have been reported, and include the reaction of isatin with sodium hydride, either in toluene under reflux 74 or in DMF 75 . Other methods include the use of potassium carbonate in DMF 76,77 or in acetone 78 .…”

Section: N-alkylationmentioning

confidence: 99%

“…Amongst the methods for the reduction of isatin to dioxindoles are the uses of Zn/HgCl 2 in refluxing benzene 72 and Fe/HCl in aqueous ethanol 134 , as well as eletrochemical 135 and photochemical 75 reduction. NMethylisatin can be reduced to the corresponding dioxindole in quantitative yield by reaction with potassium tetracarbonylhydridoferrate (KHFe(CO) 4 ) 136 .…”

Section: Synthesis Of Oxindoles and Dioxindolesmentioning

confidence: 99%

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The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

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: Synthesis Of Oxindoles and Dioxindolesmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

View full text Add to dashboard Cite

show abstract

“…These properties are more fully detailed in the supplementary material.In nature, isatin is found in plants of the genus Isatis, in Calanthe discolor LINDL. and in Couroupita guianensis Aubl., and has also been found as a component of the secretion from the parotid gland of Bufo frogs, and in humans as it is a metabolic derivative of adrenaline [12][13][14][15] . Substituted isatins are also found in plants, for example the melosatin alkaloids (methoxy phenylpentyl isatins)obtained from the Caribbean tumorigenic plant Melochia tomentosa as well as from fungi: 6-(3'-methylbuten-2'-yl)isatin was isolated from Streptomyces albus and 5-(3'-methylbuten-2'-yl)isatin from Chaetomium globosum.…”

Section: Introductionmentioning

confidence: 99%

“…Biological properties of isatin include a range of actions in the brain and offer protection against certain types of infections. Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro [12][13][14][15] . A series of p-substituted Isatin semicarbazones have shown anticonvulsant activity in MES, scPTZ and scSTY tests.…”

Section: Introductionmentioning

confidence: 99%

The Chemistry and Synthesis of 1H-indole-2,3-dione (Isatin) and its Derivatives

Sonawane

Tripathi

2013

ILCPA

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Isatins are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds. In this, a convenient method has been developed for the conversion of Indoles into Isatins and some heterocyclic derivative were synthesised such as 5-nitro-1H-indole-2,3-dione, 2-methylquinoline-4-carboxylic acid which may be used as raw material for drug synthesis. The general process utilizes the effective method for synthesis of Isatin from Indole is bromination and oxidation with an N-bromosuccinimide-dimethyl sulfoxide reagent. The nitration of Isatin at C-5 takes place by using KNO 3 , conc. H 2 SO 4 , 2-methylquinoline-4-caboxylic acid are usually obtained from pfitzinger reaction.

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“…Methisazone (N-methyl isatin-3-thiosemicarbazone) was found to be an effective compound against variola and vaccinia viruses and have also shown promising antimicrobial activity. The cannon ball tree possesses (Couroupita guianensis Aubl), antibiotic, antifungal, antiseptic, and analgesic qualities [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

An Extraction of the Isatin from the <i>Couroupita guianesis</i> (Cannon Ball Tree) and a Novel Synthesis of the N,N'-(2-oxo-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazole]-3',5'-diyl]diacetamidefrom the Isatin

Tripathi

Sonawane

2013

ILCPA

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Isatins are synthetically versatile substrates, where they can be used for the synthesis of a large variety of Isatins and heterocyclic compounds. In this, the isatin were extracted from the floral material of Couroupita guianesis commonly known as an Cannon ball tree. After that, a novel heterocyclic spiro derivative having an IUPAC name N,N'-(2-oxo-3'H-spiro [indoline-3,2'-[1,3,4] thiadiazole]-3'5'-diyl)diacetamide were synthesized , which may be used as raw material for drug synthesis. A spiro compound N,N'-(2-oxo-3'H-spiro[indoline-3,2'-[1,3,4] thiadiazole]-3'5'-diyl)diacetamide were synthesise by refluxing Isatin And thiosemicarbazone in ethanol and then on heating with acetic anhydride underwent to cyclization into intermediate that on acetylation of the NH and NH 2 groups afforded the spiro compound.

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Selective Photo-Reduction of 1-Alkylisatins in Degassed Alcoholic Solutions

Cited by 20 publications

References 0 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

The Chemistry and Synthesis of 1H-indole-2,3-dione (Isatin) and its Derivatives

An Extraction of the Isatin from the <i>Couroupita guianesis</i> (Cannon Ball Tree) and a Novel Synthesis of the N,N'-(2-oxo-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazole]-3',5'-diyl]diacetamidefrom the Isatin

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