482-59-7Relevant academic research and scientific papers
Dynamic Covalent Metathesis in the C=C/C=N Exchange between Knoevenagel Compounds and Imines
Gu, Ruirui,Flidrova, Karolina,Lehn, Jean-Marie
supporting information, p. 5560 - 5568 (2018/05/01)
Fast and reversible dynamic covalent C=C/C=N exchange takes place without catalyst in nonpolar solvents between barbiturate-derived Knoevenagel (Kn) compounds and imines. A detailed study of the reaction indicates that it proceeds by an associative organo-metathesis mechanism involving the formation of a four-membered ring azetidine intermediate by addition of the imine C=N group to the C=C bond of the Kn compound. This intermediate could be generated cleanly and stabilized at low temperature by condensation of the o,p-dinitrophenyl Kn derivative with the cyclic imine 1-azacyclohexene. It was characterized by extensive NMR and mass spectrometric studies. The process described represents a genuine dynamic covalent organo-metathesis through a four-membered ring adduct as intermediate. It paves the way for the exploration of a wide set of dynamic systems involving (strongly) polarized C=C bonds and various imines, extending also into covalent dynamic polymers and polymolecular assemblies.
Biomimetic investigations from reactive lysine-derived C5 units: one step synthesis of complex polycyclic alkaloids from the Nitraria genus
Gravel, Edmond,Poupon, Erwan,Hocquemiller, Reynald
, p. 5248 - 5253 (2007/10/03)
A single biomimetic cascade sequence featuring intermolecular followed by intramolecular cyclizations allowed the biomimetic synthesis of nitraramine and the formation of an interesting original cage-like structure from simple C5 lysine-derived metabolites. In the course of the study, the structure and spectral data of 1-epinitraramine were also revisited.
