ADDITION OF AMINES TO METHYL 3-DEHYDROQUINATE AND 3-DEHYDROSHIKIMATE

Authors
BALTAS M DESPEYROUX P GORRICHON L
Citation
M. Baltas et al., ADDITION OF AMINES TO METHYL 3-DEHYDROQUINATE AND 3-DEHYDROSHIKIMATE, Bioorganic & medicinal chemistry letters, 3(7), 1993, pp. 1447-1452
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
7
Year of publication
1993
Pages
1447 - 1452
Database
ISI
SICI code
0960-894X(1993)3:7<1447:AOATM3>2.0.ZU;2-8
Abstract
Reaction of 3-dehydroquinate compounds 1-3 with primary amines is stud ied in CH2Cl2 and MeOH. The reaction yields 3-dehydroshikimate 4 (in C H2Cl2) and(or) 3-alkylamino 4-hydroxybenzoate derivatives 6 or 7. The results support a Schiff base formation and an intramolecular catalysi s by a specific diamine [2-(2-(aminoethyl)pyridine]. The effects of th e imine intermediate and of the solvent on the aromatization reaction are discussed.