Synthesis 2017; 49(18): 4261-4271
DOI: 10.1055/s-0036-1588841
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Sanatan Nayak §
School of Chemistry, University of Hyderabad, Hyderabad, Telangana, 500046, India   Email: akhilchemistry12@gmail.com   Email: akssc@uohyd.ac.in
,
B. Prabagar §
School of Chemistry, University of Hyderabad, Hyderabad, Telangana, 500046, India   Email: akhilchemistry12@gmail.com   Email: akssc@uohyd.ac.in
,
Nayan Ghosh §
School of Chemistry, University of Hyderabad, Hyderabad, Telangana, 500046, India   Email: akhilchemistry12@gmail.com   Email: akssc@uohyd.ac.in
,
Rajendra K. Mallick §
School of Chemistry, University of Hyderabad, Hyderabad, Telangana, 500046, India   Email: akhilchemistry12@gmail.com   Email: akssc@uohyd.ac.in
,
School of Chemistry, University of Hyderabad, Hyderabad, Telangana, 500046, India   Email: akhilchemistry12@gmail.com   Email: akssc@uohyd.ac.in
› Author Affiliations
Further Information

Publication History

Received: 23 March 2017

Accepted after revision: 02 May 2017

Publication Date:
12 June 2017 (eFirst)

§ 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

 
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