Isatin chloride: a phantom. Reactions of 2-(2,2-dichloro-2,3-dihydro-3-oxoindol-1-yl)-3H-indol-3-one
Abstract
It is shown that 2-chloro-3H-indol-3-one 1 and analogues have never actually been isolated and that their reactions, reported over 115 years in 40 papers and 4 patents, are those of more or less impure 2-(2,2-dichloro-2,3-dihydro-3-oxoindol-1-yl)-3H-indol-3-one 14. Several reactions of the parent compound and its 5,5′-dimethyl and 5,5′-dibromo derivatives are reported, especially a reaction with dry methanol leading to the known indoloquinazoline 25 (‘methylisatoid’) and to the known alkaloid tryptanthrin 21 via a photolabile orthoester.
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