The synthesis of trianglimines:: on the scope and limitations of the [3+3] cyclocondensation reaction between (1R,2R)diaminocyclohexane and aromatic dicarboxaldehydes

被引：111

作者：

Kuhnert, N ^{[1
]}

Rossignolo, GM ^{[1
]}

Lopez-Periago, A ^{[1
]}

机构：

[1] Univ Surrey, Dept Chem, Synthet & Biol Organ Chem Lab, Guildford GU2 7XH, Surrey, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2003年 / 1卷 / 07期

关键词：

D O I：

10.1039/b212102f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of aromatic dicarboxaldehydes, using dilithiation methodology is described along with their reactivity, in the [3 + 3] cyclocondensation reaction, with (1R,2R)-diaminocyclohexane to give trianglimine macrocycles. The scope and limitations of the cyclocondensation reaction are studied and some comments on the properties of the novel macrocycles are made such as their conformation in solution and temperature dependent dynamic NMR behaviour.

引用

页码：1157 / 1170

页数：14

共 58 条

[1] STUDIES OF PENDANT-ARM MACROCYCLIC LIGANDS .1. SYNTHESIS OF 2 NEW PENTA-AZA LIGANDS, AND OBSERVATION OF PH-DEPENDENT REVERSIBLE EQUILIBRIA BETWEEN TRIGONAL-BIPYRAMIDAL AND SQUARE-PLANAR FORMS OF THEIR NICKEL(II) AND COPPER(II) COMPLEXES - CRYSTAL-STRUCTURE OF A TRIGONAL-BIPYRAMIDAL NICKEL(II) COMPLEX [J].

ALCOCK, NW ;

KINGSTON, RG ;

MOORE, P ;

PIERPOINT, C .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1984, (09) :1937-1943

[2]

Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO

[3]

2-X

[4]

Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO

[5]

2-G

[6]

Berl V, 1999, EUR J ORG CHEM, V1999, P3089

[7] Thermodynamically-controlled cyclisation and interconversion of oligocholates: metal ion templated 'living' macrolactonisation [J].

Brady, PA ;

Sanders, JKM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21) :3237-3253

[8] SYNTHESIS AND NMR CHARACTERIZATION OF A NOVEL HETEROLOGUE OF PYRENE - THE NAPHTHO[1,8-BC 4,5-B'C']DIPYRAN (1,8-DIOXAPYRENE) [J].

BUISSON, JP ;

KOTZYBA, J ;

LIEVREMONT, JP ;

DEMERSEMAN, P ;

PLATZER, N ;

BIDEAU, JP ;

COTRAIT, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (03) :739-747

[9]

BUUHOI NP, 1947, RECL TRAV CHIM PAY B, V66, P533

[10] (3+3)-Cyclocondensation of the enantiopure and racemic forms of trans-1,2-diaminocyclohexane with terephthaldehyde.: Formation of diastereomeric molecular triangles and their stereoselective solid-state stacking into microporous chiral columns [J].

Chadim, M ;

Budesínsky, M ;

Hodacová, J ;

Závada, J ;

Junk, PC .

TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :127-133

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