Recent Advances in the Synthesis of Hydrogenated Azocine-Containing­ Molecules

Abstract

This review covers recent advances in synthesis of azocinecontaining systems. The most approaches towards azocines are discussed.

Highly Diastereo- and Enantioselective Synthesis of Tetrahydrobenzo[b]azocines via Palladium-Catalyzed [4 + 4] Cycloaddition

“…Azocine derivatives are a diverse class of eight-membered N -heterocyclic compounds that frequently occur as core structures in various natural products and biologically active pharmaceuticals such as Apparicine (antinociceptive activity), Manzamine A (anticancer), and FR-900482 (antibiotic) . Despite extensive efforts to access the azocine ring system, researchers still struggle to construct chiral azocines with stereocontrol and high efficiency due to the lack of available synthetic methods, especially considering the unfavorable enthalpy and entropy factors, as well as the transannular interactions expected in such molecules . Thus, the discovery of more efficient and enantioselective routes to synthesize diverse azocine products is highly desired.…”

A Dipolar Cyclization/Fragmentation Strategy for the Catalytic Asymmetric Synthesis of Chiral Eight-Membered Lactams

“…To our knowledge, this kind of medium-sized heterocycles are popular scaffolds in many biologically active agents as exemplified in Figure 2a. [55][56][57][58][59][60] Though impressive synthetic endeavors, the catalytic asymmetric synthesis starting from easily available feedstocks are still very rare. [61][62][63] As depicted in Figure 2b, the detailed design plan consisted of two catalysis cycles.…”

Synthesis of Benzo[b]azocin‐2‐ones by Aryl Amination and Ring‐Expansion of α‐(Iodophenyl)‐β‐oxoesters

“…Synthetic routes to the azocane ring system were recently reviewed by Voskressensky . An obvious synthetic access to hexahydrobenzo[ b ]azocin‐2‐one derivatives is provided by Beckmann rearrangement of oximes from benzosuberones .…”

“…[9,10] Synthetic routes to the azocane ring system were recently reviewedb yV oskressensky. [11,12] An obvious synthetica ccess to hexahydrobenzo[b]azocin-2-one derivatives is provided by Beckmann rearrangement of oximesf rom benzosuberones. [13] Al ess evident, though very efficient access to the target structure is achievedb yo xidative cleavage of cyclopenta[b]indole derivatives with periodate.…”