Synthesis of tethered indoles in the search for conformationally controlled calixindoles: an indole 3-substituent tether

被引：13

作者：

Black, DS ^{[1
]}

Kumar, N ^{[1
]}

McConnell, DB ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

TETRAHEDRON | 2001年 / 57卷 / 11期

基金：

澳大利亚研究理事会;

关键词：

capped calix[3]indole; 3-(2-hydroxyphenyl)-4,6-dimethoxyindole; tri-indolylphenoxymethylbenzene; tetra-indolylphenoxymethylbenzene;

D O I：

10.1016/S0040-4020(01)00053-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-(2-Hydroxyphenyl)-4,6-dimethoxyindole 8 has been synthesised and linked to 1,3,5-tribromomethylbenzene and 1,2,4,5 tetrabromomethylbenzene to give the tri-indolyl and tetra-indolyl compounds 18 and 23, respectively. Attempts to generate capped calix[3]indoles and calix[4]indoles from these compounds were unsuccessful. (C) 2001 Elsevier Science Ltd. AU rights reserved.

引用

页码：2203 / 2211

页数：9

共 22 条

[1] SYNTHESIS OF ACTIVATED 3-ARYLINDOLES [J].

BLACK, DS ;

BOWYER, MC ;

BOWYER, PK ;

IVORY, AJ ;

KIM, M ;

KUMAR, N ;

MCCONNELL, DB ;

POPIOLEK, M .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (09) :1741-1750

[2] SYNTHESIS OF A NEW CLASS OF INDOLE-CONTAINING MACROCYCLES [J].

BLACK, DS ;

CRAIG, DC ;

KUMAR, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) :425-426

[3] CALIX[3]INDOLES, NEW MACROCYCLIC TRIS(INDOLYLMETHYLENE) COMPOUNDS WITH 2,7-LINKAGES [J].

BLACK, DS ;

BOWYER, MC ;

KUMAR, N ;

MITCHELL, PSR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (10) :819-821

[4] Reaction of 4,6-dimethoxy-3-methylindole with aromatic aldehydes: A simple synthesis of calix[3]indoles [J].

Black, DS ;

Craig, DC ;

Kumar, N .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1996, 49 (03) :311-318

[5] CALIX[4]INDOLES - NEW MACROCYCLIC TETRA(INDOLYLMETHYLENE) COMPOUNDS WITH 2,7-LINKAGES [J].

BLACK, DS ;

CRAIG, DC ;

KUMAR, N .

TETRAHEDRON LETTERS, 1995, 36 (44) :8075-8078

[6] Formation of C-amido-calix[3]indoles from 2′- and 7′-indolylglyoxylamides [J].

Black, DS ;

Kumar, N ;

McConnell, DB .

TETRAHEDRON, 2000, 56 (43) :8513-8524

[7] INVESTIGATION OF THE BISCHLER INDOLE SYNTHESIS FROM 3,5-DIMETHOXYANILINE [J].

BLACK, DSC ;

GATEHOUSE, BMKC ;

THEOBALD, F ;

WONG, LCH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (02) :343-350

[8] THE 1ST EXAMPLE OF A NEW CLASS OF BRIDGED CALIXARENE [J].

BOHMER, V ;

GOLDMANN, H ;

VOGT, W .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) :667-668

[9] PHOTO-CIDNP STUDIES ON CALIXARENES AND BRIDGED CALIXARENES [J].

BOHMER, V ;

GOLDMANN, H ;

KAPTEIN, R ;

ZETTA, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) :1358-1360

[10] THE MECHANISM OF INDOLE FORMATION FROM PHENACYLARYLAMINES .2. THE STABILITY AND REACTIONS OF PHENACYL-NORMAL-ALKYLARYLAMINES [J].

BROWN, F ;

MANN, FG .

JOURNAL OF THE CHEMICAL SOCIETY, 1948, (JUN) :847-858

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