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ChemInform Abstract: Synthesis of Substituted 2-Pyridones via the Pummerer Cyclization—Deprotonation—Cycloaddition Cascade of Imidosulfoxides.

✍ Scribed by Albert Padwa; Todd M. Heidelbaugh; Jeffrey T. Kuethe

Publisher
John Wiley and Sons
Year
2010
Weight
38 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of Substituted 2-Pyridones via the Pummerer Cyclization-Deprotonation-Cycloaddition Cascade of Imidosulfoxides.

-The Pummerer reaction of imidosulfoxides represents a highly efficient method for the synthesis of azapolycyclic ring systems. The subsequent ring cleavage reaction of the initially formed isomuenchnone cycloadduct, e.g. (III), appears to be dependent upon stereoelectronic factors associated with the amide lone pair of electrons and the oxygen bridge. Several imidosulfoxides containing a tethered alkenyl group are subjected to Pummerer reaction conditions. The resulting mesoionic dipoles formed by a cyclization/deprotonation sequence undergo ready dipolar cycloadditions across the pendant olefin to afford intramolecular cycloadducts in high yields.

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