Acid-Catalyzed Synthesis of Isatoic Anhydride-8-Secondary Amides Enables IASA Transformations for Medicinal Chemistry

Sudershan R. Gondi, Althaf Shaik, Kenneth D. Westover

Research output: Contribution to journalArticlepeer-review

Abstract

Quinazolin-dione-N-3-alklyl derivatives are the core scaffolds for several categories of bioactive small molecules, but current synthetic methods are costly, involve environmental hazards, and are not uniformly scalable. Here, we report an inexpensive, flexible, and scalable method for the one-pot synthesis of substituted quinazolin-dione-N-3-alkyls (isomers of isatoic-8-secondary amides (IASAs)) from isatin that take advantage of in situ capture of imidic acid under acidic conditions. We further show that this method can be used for the synthesis of a wide variety of derivatives with medicinal uses.

Original languageEnglish (US)
Pages (from-to)125-136
Number of pages12
JournalJournal of Organic Chemistry
Volume87
Issue number1
DOIs
StatePublished - Jan 7 2022

ASJC Scopus subject areas

  • Organic Chemistry

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