M. Baltas, P. Despeyroux, L. Gorrichon
Jul 1, 1993
Citations
0
Influential Citations
5
Citations
Journal
Bioorganic & Medicinal Chemistry Letters
Abstract
Abstract Reaction of 3-dehydroquinate compounds 1–3 with primary amines is studied in CH 2 Cl 2 and MeOH. The reaction yields 3-dehydroshikimate 4 (in CH 2 Cl 2 ) and(or) 3-alkylamino 4-hydroxybenzoate derivatives 6 or 7 . The results support a Schiff base formation and an intramolecular catalysis by a specific diamine [2-(2-(aminoethyl)pyridine]. The effects of the imine intermediate and of the solvent on the aromatization reactions are discussed.