123rd General Meeting of the KCS

Type Poster Presentation
Area Medicinal Chemistry
Room No. Exhibition Hall 2
Time 4월 18일 (목요일) 11:00~12:30
Code MEDI.P-410
Subject The reactivity of MBH adducts with benzylamines to access the 2-benzazepines under Rh(III) catalysis
Authors Neeraj kumar Mishra, Prithwish Ghosh, Won An, In Su Kim*
School of Pharmacy, Sungkyunkwan University, Korea
Abstract The directing group assisted transition-metal-catalyzed C–H activation has been one of the most attractive issues in organic synthesis due to their site selective C–H bond functionalization, easy to remove after reaction and undergo annulation reaction to offered new biologically active heterocyclic scaffolds. In this addition, free NH2 group as a directing group is less explored because of its poisoning nature for the transition-metal. The Morita–Baylis–Hillman adduct (MBH) has been recognized as a useful 3-carbon synthon in C–C bond formation reactions. Azepine analogues are among the most interesting discovery in the field of natural products and pharmaceuticals. Particularly, benzazepine derivatives have attracted considerable attention by virtue of their interesting biological properties. Typical examples, such as galanthamine, capsazepine, and baclabuvir include the 2-benzazepine scaffold. Therefore, the synthesis of 2-benzazepines is of great interest in organic and medicinal chemistry. In this presentation, the rhodium(III)-catalyzed cross-coupling reaction between commercially available benzylamines and Morita–Baylis–Hillman adducts is described. This protocol provides a facile route for synthesis of various 2-benzazepine derivatives via C(sp2)–H activation of in situ generated N-allyl benzylamines from MBH adduct and subsequent intramolecular olefin insertion process. To gain mechanistic insight of this transformation, DFT calculations were also performed.
E-mail neerajchemistry@gmail.com