Ag(I)-Catalyzed Cycloisomerization and Cyclization of Ketene Aminals: Construction of Azepine and 1,2-Dihydropyridine Derivatives

§ These authors contributed equally.
Dedicated to Dr. Vijay Nair, NIIST, Trivandrum for his 75th Birthday
Published as part of the Special Topic Modern Cyclization Strategies in Synthesis

Abstract

Silver-catalyzed cyclization and cycloisomerization of ketene N,N-acetals at room temperature has been developed to access a variety of highly substituted cyclobutene-fused azepine and 1,2-dihydropyridine derivatives. This cost-effective method is reliably implemented for the gram-scale synthesis of azepine and dihydropyridine derivatives. The iodo group in the periphery of the dihydropyridine motif can be functionalized with both Suzuki and Sonogashira reactions.

Key words

azepine - dihydropyridine - cycloisomerization - ketene aminals

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