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Synthesis 2011(22): 3697-3705
DOI: 10.1055/s-0030-1260235
DOI: 10.1055/s-0030-1260235
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Indolin-2-one, Isoindolin-1-one, and Indole Derivatives from Homophthalic Acid
Weitere Informationen
Received
21 July 2011
Publikationsdatum:
21. September 2011 (online)
Publikationsverlauf
Publikationsdatum:
21. September 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201122/lookinside/thumbnails/10.1055-s-0030-1260235-1.jpg)
Abstract
We hereby report the preparation of indolin-2-one and isoindolin-1-one and their derivatives starting from 2-(carboxymethyl)benzoic acid, which was first regiospecifically converted into the isomeric half esters. Transformation of the acid functionalities to the acyl azides followed by Curtius rearrangement gave the regioisomeric isocyanates. Reaction of the isocyanates with aniline produced urethane derivatives. Intramolecular cyclization provided the target compounds.
Key words
amides - azides - fused-ring systems - heterocycles - indoles
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