The chemistry of isatins: a review from 1975 to 1999 by Silva J.F.M. da

By Silva J.F.M. da

Isatins (1H-indole-2,3-dione) are synthetically flexible substrates, the place they are often used for the synthesis of a big number of heterocyclic compounds, reminiscent of indoles and quinolines, and as uncooked fabric for drug synthesis. Isatins have additionally been present in mammalian tissue and their functionality as a modulator of biochemical approaches has been the topic of numerous discussions. The advances within the use of isatins for natural synthesis over the past twenty-five years, in addition to a survey of its organic and pharmacological houses are suggested during this assessment and within the accompanying supplementary info.

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The initial products obtained can suffer further reaction in the presence of a second nucleophilic group to give cyclization products. For didactic reasons, these reactions have been sorted by the nature of the nucleophile. 1 - Amines and related compounds a) Ammonia, hydroxylamine and hydrazine Isatin reacts with ammonium hydroxide or ammonium acetate to furnish a mixture of compounds. Amongst them are isamic acid and its corresponding amide, isamide. Since 1877 there had been a discussion as to their structure, which in 1976 was finally elucidated, by Sir John Cornforth on the basis of chemical and spectroscopic data228.

Isatin oximes can be acylated simultaneously at the heterocyclic ring nitrogen and at the oxime oxygen by reaction with anhydrides or acid chlorides231. While these products are derived from the nucleophilic attack at the C-3 carbonyl, the reaction of N-acylisatins with the respective nucleophiles results in opening of the heterocyclic ring. com/orgchem/0010004 Uploaded 17 October 2000 at 14:44 GMT Please use CPS: orgchem/0010004 in any reference to this article 43 heterocyclic ring cleavage. The benzoylformamides obtained in these cases further react with a second equivalent of ammonia to produce quinazoline derivatives (Scheme 52).

1-Acetyl-3-dicyanomethyleneisatin undergoes a substitution reaction with aniline, in nonpolar solvents, leading to a cyanoenamine334 (Scheme 77). com/orgchem/0010004 Uploaded 17 October 2000 at 14:44 GMT Please use CPS: orgchem/0010004 in any reference to this article 60 NC O N NC CN PhNH2 (68%) O NHPh O N O Scheme 77 The reactivity of isatin derivatives towards ortho-aminophenol and orthoaminothiophenol has been the subject of a number of reports and some of the products obtained are quite intriguing.

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