K. Revathy and A. Lalitha (RSC Adv. 2014, 4, 279-285) reported the concerted, suprafacial, [4S + 2S] cycloaddition of an azomethine ylide with a chalcone to produce a variety of spiropyrrolizidenes. The azomethine ylide is generated in situ via the decarboxylation of an iminium ion formed from the reaction of proline and an isatin. We have used a Suzuki reaction to prepare a series of 5- and 6-aryl-substuted isatins from the corresponding brominated precursors, and are using these substrates in a three component condensation reaction with proline and methyl cinnamate (instead of a chalcone) to produce new spiropyrrolizidenes. Spiropyrrolizidines have been found to have anti-cancer and anti-bacterial properties.

Synthesis of spiropyrrolizidenes from aryl-isatins, proline, and methyl cinnamate

251st National Meeting (2016)

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