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Synthesis 1980; 1980(7): 505-536
DOI: 10.1055/s-1980-29110
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The Chemistry of Isatoic Anhydride

Gary M. Coppola*
  • *Department of Medicinal Chemistry, Pharmaceutical Division, Sandoz Inc., East Hanover, New Jersey 07936, U.S.A.
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Publication Date:
15 May 2002 (online)

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A survey of the methods of preparation and reactions of isatoic anhydride is given. The reactions are classified into three major classes: substitution on nitrogen, substitution on the aromatic ring, and nucleophilic reactions. 1. Introduction 2. Synthesis of Isatoic Anhydrides 2.1. Ring Closure of Anthranilic Acids 2.2. Oxidation of Isatins 2.3. Reaction of Phthalic Anhydride with Azides 2.4. From Phthalimides 2.5. Oxidation of Phthalamic Acids 2.6. Oxidation of Indigo 2.7. Miscellaneous Preparations of Isatoic Anhydrides 2.8. Saturated Anhydrides 2.9. Hetero Anhydrides 2.10. Diisatoic Anhydrides 2.11. Polycyclic Anhydrides 3. Reactions of Isatoic Anhydrides 3.1. Substitution on Nitrogen 3.2. Substitution on the Aromatic Ring 3.3. Reaction with Water, Alcohols, and Thiols 3.4. Reaction with Amines 3.5. Reaction with Amides 3.6. Reaction with Ureas, Thioureas, and Thiopseudoureas 3.7. Reaction with Amidines and Related Compounds 3.8. Reaction with Carbanions 3.9. Miscellaneous Reactions 4. Addenda