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

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

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbodiimides / chemistry*
  • Catalysis
  • Metals / chemistry
  • Molecular Structure
  • ortho-Aminobenzoates / chemical synthesis*
  • ortho-Aminobenzoates / chemistry

Substances

  • Carbodiimides
  • Metals
  • ortho-Aminobenzoates
  • anthranilic acid