Ionic-Liquid-Supported Synthesis of Amines and Derivatives

Mansour Debdab (1) , Florence Mongin (1, 2) , J.P. Bazureau (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 CPM - Chimie et Photonique Moléculaires

Amine precursors such as glycines protected at nitrogen with a Boc or formyl group were grafted by esterification on the hydroxylated arms of 1-(2-hydroxyethyl)-3-methylimidazolium hexafluorophosphates or tetrafluoroborates. The cleavage of the Boc group was then realized at room temperature by successively treating acetonitrile solutions of the thus formed glycinates with methanol and acetyl chloride (two equivalents each). Interestingly, the resulting glycinate hydrochlorides were converted into the corresponding amines during the removal of the solvent. Ugi reaction of one of these ionic-liquid-grafted amines with phthalaldehydic acid and tert-butyl isocyanide, followed by cleavage, furnished a phthalimidine 12.

Domaines: Chimie organique

Mansour Debdab, Florence Mongin, J.P. Bazureau. Ionic-Liquid-Supported Synthesis of Amines and Derivatives. Synthesis: Journal of Synthetic Organic Chemistry, 2006, 23, pp.4046-4052. ⟨10.1055/s-2006-950309⟩. ⟨hal-00772538⟩