Synthesis of Acridines by the [4+2] Annulation of Arynes and 2-Aminoaryl Ketones

被引：82
作者：
Rogness, Donald C. [1 ]
Larock, Richard C. [1 ]
机构：
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 07期
基金：
美国国家卫生研究院;
关键词：
ANTIMICROBIAL ACTIVITY; BIOLOGICAL-ACTIVITY; TOPOISOMERASE-II; BENZYNE; ROUTE; DNA; DESIGN; THIOXANTHONES; CYCLIZATION; XANTHONES;
D O I：
10.1021/jo1000687
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of 2-aminoaryl ketones and arynes generated by the treatment of various o-(trimethylsilyl)aryl triflates with CsF results in [4 + 2] annulation to afford Substituted acridines in good yields.
引用
收藏
页码：2289 / 2295
页数：7
相关论文
共 55 条
[1]   Design, synthesis, and biological properties of new bis(acridine-4-carboxamides) as anticancer agents [J].
Antonini, I ;
Polucci, P ;
Magnano, A ;
Gatto, B ;
Palumbo, M ;
Menta, E ;
Pescalli, N ;
Martelli, S .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) :3109-3115
[2]   Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides [J].
Beller, M ;
Breindl, C ;
Riermeier, TH ;
Tillack, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1403-1412
[3]   Acridine/acridone: a simple scaffold with a wide range of application in oncology [J].
Belmont, Philippe ;
Dorange, Ismet .
EXPERT OPINION ON THERAPEUTIC PATENTS, 2008, 18 (11) :1211-1224
[4]  
Bernthsen A., 1884, ANN, V224, P1
[5]  
Bernthsen A., 1878, ANN, V192, P1
[6]   Synthesis of isoquinoline-3-carboxylates and benzocyclobutanes via reaction of 2-amidoacrylate esters with arynes [J].
Blackburn, Tom ;
Ramtohul, Yeeman K. .
SYNLETT, 2008, (08) :1159-1164
[7]   Present trends and future strategy in chemotherapy of malaria [J].
Chauhan, PMS ;
Srivastava, SK .
CURRENT MEDICINAL CHEMISTRY, 2001, 8 (13) :1535-1542
[8]  
Chen Y, 2009, MODERN ARYLATION METHODS, P401, DOI 10.1002/9783527627325.ch12
[9]   Thermal ring contraction of dibenz[b,f]azepin-5-yl radicals:: New routes to pyrrolo[3,2,1-jk]carbazoles [J].
Crawford, Lynne A. ;
McNab, Hamish ;
Mount, Andrew R. ;
Wharton, Stuart I. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6642-6646
[10]  
Denny W.A., 2004, MED CHEM REV ONLINE, V1, P257, DOI DOI 10.2174/1567203043401923
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