124948-53-4Relevant academic research and scientific papers
1,3-Dipolar Cycloaddition of Imidate Ylides on Imino-Alcohols: Synthesis of New Imidazolones Using Solvent Free Conditions.
Lerestif, Jean Michel,Perrocheau, Jacques,Tonnard, Francois,Bazureau, Jean Pierre,Hamelin, Jack
, p. 6757 - 6774 (1995)
Imidates derived from α-amino esters as potential azomethine ylides, undergo 1,3-dipolar cycloaddition with imino-alcohols, in tautomeric equilibrium with 1,3-oxazolidines, without solvent at 70 deg C or under microwave irradiation.This reaction leads to a wide range of novel polyfunctionalized 4-yliden-2-imidazolin-5-ones in good yields with short reaction times.The reactivity of these imidates derived from α-amino esters with imino-alcohols is rationalized from the energy of the Frontier Molecular Orbitals (FMO) determined by semi-empirical PM3 calculations : the reaction is controlled by the interaction HOMO(1,3-dipole) - LUMO(dipolarophile) and the second order perturbation energy calculations are in agreement with the experimental reaction orientation.
An effective method to prepare imines from aldehyde, bromide/epoxide, and aqueous ammonia
Huang, Jing-Mei,Zhang, Jue-Fei,Dong, Yi,Gong, Wen
supporting information; experimental part, p. 3511 - 3514 (2011/06/22)
A three-component reaction of aldehydes, alkyl bromides, and ammonia to form imines was studied. Aqueous ammonia was applied as the nitrogen source and solvent in the reaction. For the aromatic aldehyde, the product yields are good to excellent and the reaction conditions are mild to be compatible with a range of functional groups. The reaction of aldehydes and aqueous ammonia with epoxides was also studied and imines bearing a vicinal hydroxyl group can be obtained efficiently and regioselectively. And studies showed that this method allows the synthesis of primary amines and especially 1,2-amino alcohol selectively in high yield. It is proposed that the reaction pathway might involve a key intermediate of hydrobenzamide.
