使用碳二亚胺无金属、酸催化邻位导向合成邻氨基苯甲酸衍生物

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

作者信息

Culf Adrian S, Čuperlović-Culf Miroslava, Ouellette Rodney J, Decken Andreas

机构信息

†Atlantic Cancer Research Institute, Moncton, NB E1C 8X3, Canada.

‡National Research Council of Canada, Moncton, NB E1A 7R1, Canada.

出版信息

Org Lett. 2015 Jun 5;17(11):2744-7. doi: 10.1021/acs.orglett.5b01160. Epub 2015 May 20.

DOI:10.1021/acs.orglett.5b01160

PMID:25990766

Abstract

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 S(N)Ar reaction conditions. This method proceeds regiospecifically with a range of 2-fluoroaromatic acids or esters bearing further aryl fluorine, trifluoromethyl, and cyano substituents.

摘要

本文描述了荧光邻氨基苯甲酸酯、邻氨基吡啶羧酸盐和2'-氨基-[1,1'-联苯]-2-羧酸的一锅法合成。碳二亚胺用作2-氨基官能团的来源，该官能团在S(N)Ar反应条件下插入芳环。该方法对一系列带有进一步的芳基氟、三氟甲基和氰基取代基的2-氟芳酸或酯具有区域特异性。