A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular SNAr-based cycloetherification

被引：86

作者：

Cristau, P

Vors, JP

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Aventis CropSci, F-69009 Lyon, France

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 25期

关键词：

D O I：

10.1021/ol0168420

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] From readily accessible starting materials, macrocycles with an endo aryl-aryl ether bond are synthesized in only two operations by combination of the Ugi four-component reaction and an intramolecular: SNAr reaction. The nitro group serves as an activator for the macrocyclization and provides a handle for the introduction of functional group diversity. A Ugi reaction promoted by ammonium chloride In aprotic solvent is documented for the first time.

引用

页码：4079 / 4082

页数：4

共 54 条

[1] Multiple-component condensation strategies for combinatorial library synthesis [J].

Armstrong, RW ;

Combs, AP ;

Tempest, PA ;

Brown, SD ;

Keating, TA .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131

[2] A novel three-component butenolide synthesis [J].

Beck, B ;

Magnin-Lachaux, M ;

Herdtweck, E ;

Dömling, A .

ORGANIC LETTERS, 2001, 3 (18) :2875-2878

[3] AN EASY ACCESS TO FUNCTIONALIZED DIARYL ETHERS - FORMAL TOTAL SYNTHESIS OF K-13 [J].

BEUGELMANS, R ;

BIGOT, A ;

ZHU, JP .

TETRAHEDRON LETTERS, 1994, 35 (31) :5649-5652

[4] SNAR-BASED MACROCYCLIZATION - AN APPLICATION TO THE SYNTHESIS OF VANCOMYCIN FAMILY MODELS [J].

BEUGELMANS, R ;

SINGH, GP ;

BOISCHOUSSY, M ;

CHASTANET, J ;

ZHU, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5535-5542

[5] Synthesis of rigid hydrophobic tetrazoles using an Ugi multi-component heterocyclic condensation [J].

Bienaymé, H ;

Bouzid, K .

TETRAHEDRON LETTERS, 1998, 39 (18) :2735-2738

[6]

Bienaymé H, 1998, ANGEW CHEM INT EDIT, V37, P2234, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO

[7]

2-R

[8]

Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO

[9]

2-A

[10] Synthesis of modified carboxyl binding pockets of vancomycin and teicoplanin [J].

BoisChoussy, M ;

Neuville, L ;

Beugelmans, R ;

Zhu, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9309-9322

← 1 2 3 4 5 6 →