It is well-known that spiropyrrolizidenes can be prepared through a three component condensation that involves an isatin, proline, and a dipolarophile. Isatins are also the substrate for synthesis of 3- substituted quinoline-4-carboxylic acids via the venerable Pfitzinger reaction through heating with an aceto-arene in aqueous KOH solutions. We are exploring the use of 7-bromoisatin in both types of reaction to create a diverse set of compounds.  An increase in diversity is made possible by employing a Suzuki reaction on the 7-bromoisatin component either before or after transformation to a spiropyrrolizidene or a quinoline-4-carboxylic acid. Spiropyrrolizidines have been found to have anti-cancer and anti-bacterial properties. Quinoline-4-carboxylic acids have been found to have a variety of pharmacological activities, including potent antiviral activity.<br/>

Synthesis of spiropyrrolizidenes and 3-substituted quinoline-4-carboxylic acids from 7-bromoisatin

251st National Meeting (2016)

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