Synthesis of Indolin-2-one, Isoindolin-1-one, and Indole Derivatives from Homophthalic Acid

Date

2011-11-01

Author

KILIKLI, Alper A.
Dengiz, Çağatay
OZCAN, Sevil
BALCI, METİN

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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.

Subject Keywords

Amides, Azides, Fused-ring systems, Heterocycles, Indoles

URI

https://hdl.handle.net/11511/35566

Journal

SYNTHESIS-STUTTGART

DOI

https://doi.org/10.1055/s-0030-1260235

Collections

Department of Chemistry, Article

Citation Formats

A. A. KILIKLI, Ç. Dengiz, S. OZCAN, and M. BALCI, “Synthesis of Indolin-2-one, Isoindolin-1-one, and Indole Derivatives from Homophthalic Acid,” SYNTHESIS-STUTTGART, no. 22, pp. 3697–3705, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35566.