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

被引：7

作者：

BALTAS, M ^{[1
]}

DESPEYROUX, P ^{[1
]}

GORRICHON, L ^{[1
]}

机构：

[1] UNIV TOULOUSE 3, CNRS, SYNTH & PHYSICOCHIM ORGAN LAB, 118 ROUTE NARBONNE, F-31062 TOULOUSE, FRANCE

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 07期

关键词：

D O I：

10.1016/S0960-894X(01)80427-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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-(aminoethyl)pyridine]. The effects of the imine intermediate and of the solvent on the aromatization reaction are discussed.

引用

页码：1447 / 1452

页数：6

共 31 条

[1] INHIBITION OF EPSP SYNTHASE BY ANALOGS OF THE TETRAHEDRAL INTERMEDIATE AND OF EPSP
ALBERG, DG
LAUHON, CT
NYFELER, R
FASSLER, A
BARTLETT, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) : 3535 - 3546
[2] A TETRAHEDRAL INTERMEDIATE IN THE EPSP SYNTHASE REACTION OBSERVED BY RAPID QUENCH KINETICS
ANDERSON, KS
SIKORSKI, JA
JOHNSON, KA
[J]. BIOCHEMISTRY, 1988, 27 (19) : 7395 - 7406
[3] Bartlett P. A., 1986, RECENT ADV PHYTOCHEM, V20, P119
[4] STUDIES ON QUINIC ACID BIOSYNTHESIS IN QUERCUS-PEDUNCULATA EHRH SEEDLINGS
BOUDET, AM
[J]. PLANT AND CELL PHYSIOLOGY, 1980, 21 (05) : 785 - 792
[5] REACTIVITY STUDIES IN THE SHIKIMIC ACID SERIES
BOWLES, S
CAMPBELL, MM
SAINSBURY, M
DAVIES, GM
[J]. TETRAHEDRON LETTERS, 1989, 30 (28) : 3711 - 3714
[6] REACTIVITY STUDIES IN THE SHIKIMIC ACID SERIES - THE SYNTHESIS OF RACEMIC METHYL 6-ALPHA-FLUOROSHIKIMATE
BOWLES, SA
CAMPBELL, MM
SAINSBURY, M
DAVIES, GM
[J]. TETRAHEDRON, 1990, 46 (11) : 3981 - 3992
[7] KINETICS AND MECHANISM OF HYDROLYSIS OF 2,2,2-TRIFLUORO-N-(3-METHYL-2-CYCLOHEXENYLIDENE)ETHYLAMINE - ALPHA, BETA-UNSATURATED SCHIFF-BASE
BRAULT, M
POLLACK, RM
BEVINS, CL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) : 346 - 350
[8] AFFINITY LABELING OF ESCHERICHIA-COLI DEHYDROQUINASE
BUGG, TDH
ABELL, C
COGGINS, JR
[J]. TETRAHEDRON LETTERS, 1988, 29 (51) : 6783 - 6786
[9] SPECIFICITY OF ESCHERICHIA-COLI SHIKIMATE DEHYDROGENASE TOWARDS ANALOGS OF 3-DEHYDROSHIKIMIC ACID
BUGG, TDH
ABELL, C
COGGINS, JR
[J]. TETRAHEDRON LETTERS, 1988, 29 (51) : 6779 - 6782
[10] MECHANISM OF DEHYDROQUINASE CATALYZED DEHYDRATION .1. FORMATION OF A SCHIFF-BASE INTERMEDIATE
BUTLER, JR
ALWORTH, WL
NUGENT, MJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (05) : 1617 - 1618

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