Synthesis, Crystal Structures and Properties of Ferrocenyl Bis-Amide Derivatives Yielded via the Ugi Four-Component Reaction

Abstract

Ten ferrocenyl bis-amide derivatives were successfully synthesized via the Ugi four-component reaction by treating ferrocenecarboxylic acid with diverse aldehydes, amines, and isocyanides in methanol solution. Their chemical structures were fully characterized by IR, NMR, HR-MS, and X-ray diffraction analyses. They feature unique molecular morphologies and create a 14-membered ring motif in the centro-symmetric dimers generated in the solid state. Moreover, the electrochemical behavior of these ferrocenyl bis-amides was assessed by cyclic voltammetry.

Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds

“…Isocyanides are versatile building blocks and intermediates in chemical synthesis with wide applications for their unique structures and reactivities . Besides the well-known multicomponent Ugi , and Passerini reactions, isocyanides insertion and cyclization reaction powerful strategies for the preparation of nitrogen-containing heterocycles. , In view of their high reaction activities and variabilities, the application of isocyanides has drawn considerable attention. Notably, 2-isocyano­aceto­phenone derivatives were easily available starting materials for the construction of various heterocyclic compounds in recent years. − In 2009, Konishi and co-workers reported a simple method for the synthesis of 4-alkylidene-4 H -3,1-benzoxazine derivatives via acid-catalyzed cyclization of 2-isocyanophenyl ketones in the presence of vinyl ether .…”

Chemoselective Double Annulation of Two Different Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles

“…Due to their unique structures and reactivities, isocyanides are versatile building blocks in chemical synthesis . Beside the well-known multicomponent Ugi , and Passerini reaction, isocyanide-based [3 + n ] and [1 + m ] annulations became the most powerful tools for the preparation of heterocycles in recent years. Generally, activated methylene isocyanides act as three-atom components and react with polar multiple bonds, , 1,3-dipole, or 1,6-dipole to participate in the [3 + n ] reaction, and isocyanides can also act as a one-atom component to participate in the [1 + m ] reactions .…”