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Synthesis 2011(22): 3697-3705  
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

Alper A. Kilikli, Cagatay Dengiz, Sevil Özcan, Metin Balci*
Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey
Fax: +90(312)2103200; e-Mail: mbalci@metu.edu.tr;
Further Information

Publication History

Received 21 July 2011
Publication Date:
21 September 2011 (online)

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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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