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Part – B Studies on isatin derivatives…..
B.1 INTRODUCTION TO ISATIN
Isatin (1H-indole-2, 3-dione; C8H5NO2) is an aromatic heterocyclic
organic compound. It has a bicyclic structure, consisting of a six-membered
benzene ring fused to a five-membered nitrogen-containing ring. The
compound's structure is based on the indoline structure but where two
carbonyl groups are situated at 2- and 3-position of the five membered ring.
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In the course of studies of the action of various oxidizing agents on
indigo, Erdmann 1-3 and Laurent 4-7 in 1841 independently discovered an
oxidation product, which had the formula C8H6NO2 and to which the name
given was isatin.
In nature, isatin is found in plants of the genus Isatis, 8 in Calanthe
discolor LINDL. 9 and in Couroupita guianensis Aubl. 10 and has also been
found as a component of the secretion from the parotid gland of Bufo frogs, 11
and in humans as it is a metabolic derivative of adrenaline. 12-14 Substituted
isatins are also found in plants, for example the melosatin alkaloids (methoxy
phenylpentyl isatins) obtained from the Caribbean tumorigenic plant Melochia
tomentosa 15-17 as well as from fungi: 6-(3'-methylbuten-2'-yl)isatin was
isolated from Streptomyces albus 18 and 5-(3'-methylbuten-2'-yl)isatin from
Chaetomium globosum. 19 Isatin has also been found to be a component of
coal tar. 20
Department of Chemistry, Saurashtra University, Rajkot-360 005 113
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Fig. B.1.1
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