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Chapter – 4 Studies on different types of reactions…..
Oxindole was also prepared by Suida 38 through the reduction of 2acetaminomandelic
acid by either hydroiodic acid and phosphorous or sodium
amalgam.
A procedure developed by Hinsberg 39, 40 serves for the preparation of
N-alkyloxindoles. A secondary aromatic amine is condenced with the
sodiumbisulphite addition compound of glyoxal; the resulting product gives an
N-alkyl oxindole on treatment with aqueous hydrochloric acid.
Oxindole was obtained by Mazzaro and Borgo 41 by steam distillation in
the presence of hydrochloric acid of the product obtained when oxindole is
treated with sulfuryl chloride.
N-alkylindoles and N-substituted indole-α-carboxylicacids have been
converted into the corresponding oxindoles by Colman 42 and Michaelis. 43
Brunner 44-46 prepared oxindole by heating β-derivative of many
substituted oxindoles especially 3, 3-acetylphenylhydrazine with lime at 200-
220°C this procedure has been extended by Brunner 47 and by others 48-52 to
the preparation dialkylderivatives of oxindole.
Another convenient and general method for the preparation of oxindole
and of N-substituted oxindoles is that of Stolle. 53-57 An α-halogenated acid
chloride or bromide is condensed with an aromatic amine. Subsequent ring
closure with aluminiumchloride yields the corresponding oxindole.
In the course of the investigation of the structure of physostigmine
(esertine) Stedman and Barger 58 obtained the oxindole derivatives as a
degradation product. Catalytic reduction of oxindole derivative gives
physostigmine.
6-aminooxindole was prepared by Gabrial and Meyer 59 by the
reduction of 2, 4-dinitrophenylaceticacid with tin and hydrochloric acid.
Department of Chemistry, Saurashtra University, Rajkot – 360 005 192