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

Adrian S. Culf | Zendy; Miroslava ČuperlovićCulf | Zendy; Rodney J. Ouellette | Zendy; A. Decken | Zendy

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

Author(s) -

Adrian S. Culf,

Miroslava ČuperlovićCulf,

Rodney J. Ouellette,

A. Decken

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b01160

Subject(s) - chemistry , anthranilic acid , catalysis , biphenyl , trifluoromethyl , aryl , ring (chemistry) , organic chemistry , ligand (biochemistry) , medicinal chemistry , receptor , alkyl , biochemistry

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.

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