A simple, two-step synthesis of 3-iodoindoles

被引:146
作者
Amjad, M [1 ]
Knight, DW [1 ]
机构
[1] Cardiff Univ, Cardiff Sch Chem, Cardiff CF10 3TB, S Glam, Wales
关键词
5-endo-dig; iodocyclisation; sonogashira; indole; synthesis;
D O I
10.1016/j.tetlet.2003.10.207
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Halo-anilines, protected as the corresponding sulfonamides or carbamates, can be converted very efficiently into 3-iodoindoles by sequential Sonogashira coupling with a 1-alkyne and 5-endo-dig iodocyclisation. Azaindoles can also be obtained using this methodology. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:539 / 541
页数:3
相关论文
共 22 条
[1]  
Areadi A., 1999, SYNLETT, P1432
[2]   IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].
Barluenga, J ;
Trincado, M ;
Rubio, E ;
González, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409
[3]   A brief synthesis of beta-iodofurans [J].
Bew, SP ;
Knight, DW .
CHEMICAL COMMUNICATIONS, 1996, (09) :1007-1008
[4]   A VERSATILE 2-STAGE SYNTHESIS OF 2-SUBSTITUTED BENZO[B]FURANS FROM (2-METHOXYPHENYL)ETHYNES [J].
BUCKLE, DR ;
ROCKELL, CJM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2443-2446
[5]   REGIOSPECIFIC PALLADIUM CATALYZED TANDEM CYCLISATION-ANION CAPTURE PROCESSES - STEREOSPECIFIC GROUP TRANSFER FROM ORGANOZINC AND ORGANOBORON REAGENTS [J].
BURNS, B ;
GRIGG, R ;
SRIDHARAN, V ;
STEVENSON, P ;
SUKIRTHALINGAM, S ;
WORAKUN, T .
TETRAHEDRON LETTERS, 1989, 30 (09) :1135-1138
[6]   DBU, a highly efficient reagent for the facile regeneration of (hetero)arylamines from their acetamides and benzamides: Influence of solvent, temperature, and microwave irradiation [J].
Chakrabarty, M ;
Ghosh, N ;
Khasnobis, S ;
Chakrabarty, M .
SYNTHETIC COMMUNICATIONS, 2002, 32 (02) :265-272
[7]   Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols [J].
El-Taeb, GMM ;
Evans, AB ;
Jones, S ;
Knight, DW .
TETRAHEDRON LETTERS, 2001, 42 (34) :5945-5948
[8]   Sequential one-pot Rh(I)/Pd(0) catalysed cycloaddition-cyclisation-anion capture. Assembly of polyfunctional compounds [J].
Grigg, R ;
Sridharan, V ;
Zhang, J .
TETRAHEDRON LETTERS, 1999, 40 (47) :8277-8280
[9]  
HASKINS CM, TETRAHEDRON LETT, V45
[10]  
Knight DW, 2002, PROG HET CH, V14, P19