Regioselective synthesis of 3,4,5-trisubstituted 2-aminofurans.

Date publication

juillet 2014

Journal

Organic & biomolecular chemistry

Auteurs

Membres identifiés du Cancéropôle Est :
Pr GUILLAUME Dominique

Tous les auteurs :
Huynh TN, Retailleau P, Denhez C, Nguyen KP, Guillaume D

Lien Pubmed

https://www.ncbi.nlm.nih.gov/pubmed/24931912

Résumé

Three series of methyl 5-substituted 2-aminofuran-4-keto-3-carboxylates have been prepared following a multicomponent reaction strategy by the addition of an isocyanide to 4-oxo-2-butynoate in the presence of an aldehyde. The cycloaddition regioselectivity is generally high (>95%) but decreases when an electron-rich substituent is located at the butynoate 4-position.

Mots clés

Aldehydes, chemistry, Carboxylic Acids, chemical synthesis, Cyanides, chemistry, Cycloaddition Reaction, Fatty Acids, Monounsaturated, chemistry, Furans, chemical synthesis, Stereoisomerism

Référence

Org. Biomol. Chem.. 2014 Jul;12(28):5098-101