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DOI: 10.1055/s-0036-1588841
Ag(I)-Catalyzed Cycloisomerization and Cyclization of Ketene Aminals: Construction of Azepine and 1,2-Dihydropyridine Derivatives
Publication History
Received: 23 March 2017
Accepted after revision: 02 May 2017
Publication Date:
12 June 2017 (online)
§ 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.
Supporting Information
- Supporting Information 1H and 13C NMR, and X-ray crystallographic data of 3a (CCDC number 1539579) for this article is available online at
https://doi.org/10.1055/s-0036-1588841.
- Supporting Information
- CIF File
-
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For selected examples of cycloisomerization of N-tethered 1,n-diynes, see:
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For metal-catalyzed synthesis of azepines, see:
For reviews on Ag-catalyzed reactions, see:
For selected silver-catalyzed activation of C–C triple bonds, see: