Synthesis of heterocyclic compounds by the cyclization of isatin and its derivatives (review)

Shvekhgeimer, M.-G. A.

doi:10.1007/bf01169241

Cited by 36 publications

(26 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In a similar manner, 1-acylisatins can be reduced to 1-alkylindoles by BH 3 .THF in high yields 99 (Scheme 38).…”

Section: Scheme 35mentioning

confidence: 99%

“…In addition to the use of H 2 SO 4 for the cyclization step, isonitrosoacetanilides can be heated in BF 3 .Et 2 O at 90 o C. After cooling the reaction mixture, addition of water allows isolation of the respective isatins. This methodology has proved to be particularly effective for the preparation of benzo-oxygenated isatin derivatives 22,23 The Sandmeyer synthesis has been described as being inapplicable to ortho-hydroxy or ortho-alkoxyanilines.…”

Section: Methodsmentioning

confidence: 99%

“…Reaction with Nchlorosuccinimide generates the unstable 3-chloro-3-methylthio-2-oxindoles, which were hydrolyzed to isatins in the presence of red mercuric oxide and BF 3 .Et 2 O in aqueous THF. Hydrolysis in the absence of these reagents gave a mixture of the isatin and the 3,3-dimethylthio-2-oxindole ketal 42 .…”

Section: The Gassman Proceduresmentioning

confidence: 99%

“…In this method anilines are reacted with oxalyl chloride to form an intermediate chlorooxalylanilide which can be cyclized in the presence of a Lewis acid, usually aluminum chloride or BF 3 .Et 2 O 33 , although TiCl 4 34 has also been used to give the corresponding isatin. This method has been used for the synthesis of 1-aryl 35,36 and polycyclic isatins derived from phenoxazine, phenothiazine and dibenzoazepine 37 as well as indoline 38 .…”

Section: The Stolle Proceduresmentioning

confidence: 99%

“…Three reviews have been published regarding the chemistry of this compound: the first by Sumpter, in 1954 1 , a second by Popp in 1975 2 , and the third on the utility of isatin as a precursor for the synthesis of other heterocyclic compounds 3 . The synthetic versatility of isatin has stemmed from the interest in the biological and pharmacological properties of its derivatives.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

858

447

View full text Add to dashboard Cite

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.

show abstract

“…In a similar manner, 1-acylisatins can be reduced to 1-alkylindoles by BH 3 .THF in high yields 99 (Scheme 38).…”

Section: Scheme 35mentioning

confidence: 99%