Products from dehydration of dicarboxylic acids derived from anthranilic acid

Organic & Biomolecular Chemistry Pub Date: 2003-09-04 DOI: 10.1039/B306032B

Abstract

Treatment of N-(carboxymethyl)-anthranilic acids 1 with several dehydrating agents, gave the cyclic ortho amides 6, or the 7-membered anhydrides 7. After reaction of N-(carboxymethyl)-anthranilic acid (1a) with acetic anhydride, a diacetylated fused diketopiperazine indole dimer (18) could be isolated. Dehydrations of 2,2′-iminobis-benzoic acid led to the corresponding cyclic ortho amides 23. The dynamic behaviour of some of these compounds, and their precursors, was studied.

Graphical abstract: Products from dehydration of dicarboxylic acids derived from anthranilic acid
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