Addition of amines to methyl 3-dehydroquinate and 3-dehydroshikimate

Bioorganic & Medicinal Chemistry Letters
1993.0

Abstract

Reaction of 3-dehydroquinate compounds 1-3 with primary amines is studied in CH2Cl2 and MeOH. The reaction yields 3-dehydroshikimate 4 (in CH2Cl2) 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-(aminocthyl)pyridine]. The effects of the imine intermediate and of the solvent on the aromatization reaction are discussed.

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