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

KILIKLI A. A., DENGİZ Ç., OZCAN S., BALCI M.

SYNTHESIS-STUTTGART, no.22, pp.3697-3705, 2011 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2011
  • Doi Number: 10.1055/s-0030-1260235
  • Journal Name: SYNTHESIS-STUTTGART
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3697-3705
  • Keywords: amides, azides, fused-ring systems, heterocycles, indoles, TYROSINE KINASE INHIBITORS, EFFICIENT, REARRANGEMENT, CONSTRUCTION, CYCLIZATION, DISCOVERY, SKELETON, PROFILE
  • Middle East Technical University Affiliated: Yes

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.