Applications of Bartoli indole synthesis

被引:203
作者
Bartoli, Giuseppe [1 ]
Dalpozzo, Renato [2 ]
Nardi, Monica [2 ]
机构
[1] Univ Bologna, Dipartimento Chim Ind Toso Montanari, I-40136 Bologna, Italy
[2] Univ Calabria, Dipartimento Chim & Tecnol Chim, I-87036 Arcavacata Di Rende, Cs, Italy
关键词
EP3 RECEPTOR ANTAGONIST; VINYL GRIGNARD-REAGENTS; IMINE CHELATE LIGANDS; GENERAL-METHOD; SUBSTITUTED INDOLES; TITANIUM COMPLEXES; ANION RECEPTORS; POTENT; DERIVATIVES; DISCOVERY;
D O I
10.1039/c4cs00045e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In 1989, the reaction of vinyl magnesium halides with ortho-substituted nitroarenes leading to indoles was discovered. This reaction is now frequently reported as the "Bartoli reaction'' or the "Bartoli indole synthesis'' (BIS). It has rapidly become the shortest and most flexible route to 7-substituted indoles, because the classical indole syntheses generally fail in their preparation. The flexibility of the Bartoli reaction is great as it can be extended to heteroaromatic nitro derivatives and can be run on solid support. This review will focus on the use of the Bartoli indole synthesis as the key step in preparations of complex indoles, which appeared in the literature in the last few years.
引用
收藏
页码:4728 / 4750
页数:23
相关论文
共 154 条
[1]   Fused quinolines. Recent synthetic approaches to azoloquinolines. A review [J].
Abass, M .
HETEROCYCLES, 2005, 65 (04) :901-965
[2]   One-Pot Construction of 3,3′-Bisindolylmethanes through Bartoli Indole Synthesis [J].
Abe, Takumi ;
Nakamura, Shuuhei ;
Yanada, Reiko ;
Choshi, Tominari ;
Hibino, Satoshi ;
Ishikura, Minoru .
ORGANIC LETTERS, 2013, 15 (14) :3622-3625
[3]   Pyrrolo(iso)quinoline derivatives as 5-HT2C receptor agonists [J].
Adams, DR ;
Bentley, JM ;
Benwell, KR ;
Bickerdike, MJ ;
Bodkin, CD ;
Cliffe, IA ;
Dourish, CT ;
George, AR ;
Kennett, GA ;
Knight, AR ;
Malcolm, CS ;
Mansell, HL ;
Misra, A ;
Quirk, K ;
Roffey, JRA ;
Vickers, SP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (03) :677-680
[4]   Potent inhibition of Ca2+-dependent activation of calpain-1 by novel mercaptoacrylates [J].
Adams, Sarah E. ;
Parr, Christian ;
Miller, David J. ;
Allemann, Rudolf K. ;
Hallett, Maurice B. .
MEDCHEMCOMM, 2012, 3 (05) :566-570
[5]   Bicyclic heteroarylpiperazines as selective brain penetrant 5-HT6 receptor antagonists [J].
Ahmed, M ;
Briggs, MA ;
Bromidge, SM ;
Buck, T ;
Campbell, L ;
Deeks, NJ ;
Garner, A ;
Gordon, L ;
Hamprecht, DW ;
Holland, V ;
Johnson, CN ;
Medhurst, AD ;
Mitchell, DJ ;
Moss, SF ;
Powles, J ;
Seal, JT ;
Stean, TO ;
Stemp, G ;
Thompson, M ;
Trail, B ;
Upton, N ;
Winborn, K ;
Witty, DR .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (21) :4867-4871
[6]   Preparation of novel aza-1,7-annulated indoles and their conversion to potent indolocarbazole kinase inhibitors [J].
Al-awar, RS ;
Ray, JE ;
Hecker, KA ;
Joseph, S ;
Huang, JP ;
Shih, C ;
Brooks, HB ;
Spencer, CD ;
Watkins, SC ;
Schultz, RM ;
Considine, EL ;
Faul, MM ;
Sullivan, KA ;
Kolis, SP ;
Carr, MA ;
Zhang, FM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (15) :3925-3928
[7]  
[Anonymous], [No title captured]
[8]  
[Anonymous], [No title captured]
[9]  
[Anonymous], 2007, ADV ORG CHEM
[10]  
[Anonymous], [No title captured]