Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols

被引：59

作者：

El-Taeb, GMM ^{[1
]}

Evans, AB ^{[1
]}

Jones, S ^{[1
]}

Knight, DW ^{[1
]}

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 34期

基金：

英国工程与自然科学研究理事会;

关键词：

iodocyclisation; 5-endo-dig; beta-iodofurans; 3-alkyne-1,2-diols; furans;

D O I：

10.1016/S0040-4039(01)01112-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodocyclisations of 3-alkyne-1,2-diols, obtained from acetylides and a-hydroxy-ketones or esters, give generally excellent yields of beta -iodofurans by 5-endo-dig cyclisation followed by dehydration. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5945 / 5948

页数：4

共 22 条

[1] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F .

TETRAHEDRON LETTERS, 1989, 30 (19) :2581-2584

[2] Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction [J].

Aschwanden, P ;

Frantz, DE ;

Carreira, EM .

ORGANIC LETTERS, 2000, 2 (15) :2331-2333

[3]

BALDWIN JE, 1975, J CHEM SOC CHEM COMM, V734, P738

[4] Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols [J].

Bedford, SB ;

Bell, KE ;

Bennett, F ;

Hayes, CJ ;

Knight, DW ;

Shaw, DE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15) :2143-2153

[5] Stereochemical features of iodocyclisations of 3-alkene-1,2-diols to β-hydroxytetrahydrofurans [J].

Bew, SP ;

Barks, JM ;

Knight, DW ;

Middleton, RJ .

TETRAHEDRON LETTERS, 2000, 41 (22) :4447-4451

[6] A brief synthesis of beta-iodofurans [J].

Bew, SP ;

Knight, DW .

CHEMICAL COMMUNICATIONS, 1996, (09) :1007-1008

[7]

FABRITSY A, 1959, ZH OBSHCH KHIM+, V29, P81

[8]

FABRYCY A, 1977, ROCZ CHEM, V51, P249

[9] SYNTHESIS OF SUBSTITUTED FURANS BY PALLADIUM-CATALYZED CYCLIZATION OF ACETYLENIC KETONES [J].

FUKUDA, Y ;

SHIRAGAMI, H ;

UTIMOTO, K ;

NOZAKI, H .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5816-5819

[10]

Heaney H., 1996, Comp. Heterocycl. Chem, V2, P297

← 1 2 3 →