Acid-catalyzed synthesis of isatoic anhydride-8-secondary amides enables IASA transformations for medicinal chemistry

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dc.contributor.author Gondi, Sudershan R.
dc.contributor.author Shaik, Althaf
dc.contributor.author Westover, Kenneth D.
dc.coverage.spatial United States of America
dc.date.accessioned 2022-01-13T14:06:08Z
dc.date.available 2022-01-13T14:06:08Z
dc.date.issued 2022-01
dc.identifier.citation Gondi, Sudershan R.; Shaik, Althaf and Westover, Kenneth D., “Acid-catalyzed synthesis of isatoic anhydride-8-secondary amides enables IASA transformations for medicinal chemistry”, The Journal of Organic Chemistry, DOI: 10.1021/acs.joc.1c02036, vol. 87, no. 1, pp. 125-136, Jan. 2022. en_US
dc.identifier.issn 0022-3263
dc.identifier.issn 1520-6904
dc.identifier.uri https://doi.org/10.1021/acs.joc.1c02036
dc.identifier.uri https://repository.iitgn.ac.in/handle/123456789/7401
dc.description.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.
dc.description.statementofresponsibility by Sudershan R. Gondi, Althaf Shaik and Kenneth D. Westover
dc.format.extent vol. 87, no. 1, pp. 125-136
dc.language.iso en_US en_US
dc.publisher American Chemical Society. en_US
dc.subject Ethers en_US
dc.subject Alcohols en_US
dc.subject Amides en_US
dc.subject Reaction products en_US
dc.subject Cyclization en_US
dc.title Acid-catalyzed synthesis of isatoic anhydride-8-secondary amides enables IASA transformations for medicinal chemistry en_US
dc.type Article en_US
dc.relation.journal The Journal of Organic Chemistry


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