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A new synthesis of some indolecarboxylic acids
Author(s) -
Baiocchi Leandro,
Giannangeli Marilena
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250654
Subject(s) - chemistry , isatin , hydrolysis , indole test , organic chemistry , alkaline hydrolysis , acetic acid
1‐Substituted isatins are transformed into indole derivatives by means of ethyl chloroacetate. In fact, under the conditions of the Darzens reaction they give two glycidic ester isomers 4 and 5 which, by hydrolysis in alkaline medium, undergo a transposition to indole‐2,3‐dicarboxylic acids 2 together with minor amounts of indole‐3‐carboxylic acids 3 . From isatin itself, 2,3‐dicarboxyindole‐1‐acetic acid ( 6 ) was obtained.