Metal-Free, Acid-Catalyzed ortho-Directed Synthesis of Anthranilic Acid Derivatives Using Carbodiimides

被引:9
作者
Culf, Adrian S. [1 ]
Cuperlovic-Culf, Miroslava [2 ]
Ouellette, Rodney J. [1 ]
Decken, Andreas [3 ]
机构
[1] Atlantic Canc Res Inst, Moncton, NB E1C 8X3, Canada
[2] Natl Res Council Canada, Moncton, NB E1A 7R1, Canada
[3] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 5A3, Canada
关键词
CROSS-COUPLING REACTIONS; O-AMINOBENZOATES; BENZOIC-ACIDS; CARBONYLATION; AMINATION; FUNCTIONALIZATION; OPTIMIZATION; FLUORINATION; ACTIVATION; COMPLEXITY;
D O I
10.1021/acs.orglett.5b01160
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
One-pot syntheses of fluorescent o-aminobenzoates, o-aminopyridine carboxylates, and a 2'-amino-[1,1'-biphenyl]-2-carboxylic acid are described. Carbodiimides are used as the source of the 2-amino function which inserts onto an aromatic ring using SNAr reaction conditions. This method proceeds regiospecifically with a range of 2-fluoroaromatic acids or esters bearing further aryl fluorine, trifluoromethyl, and cyano substituents.
引用
收藏
页码:2744 / 2747
页数:4
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