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Synthesis of some benzimidazole‐ and benzothiazole‐derived ligand systems and their precursory diacids
Author(s) -
Addison Anthony W.,
Rao T. Nageswara,
Wahlgren Curtis G.
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200609
Subject(s) - benzothiazole , benzimidazole , chemistry , thioether , denticity , pyridine , medicinal chemistry , ligand (biochemistry) , mass spectrum , stereochemistry , organic chemistry , crystal structure , receptor , ion , biochemistry
Procedures are described for the preparation of various bidentate and linear tetradentate benzimidazoles and benzothiazoles incorporating units such as pyridyl and thioether, and for the preparation of certain thioether dicarboxylic acids precursory to them. Condensations of ortho ‐functinal anilines with carboxylic acids were carried out in polyphosphoric acid or refluxing HCl solution. Syntheses are reported for: [HO 2 C(CH 2 )2S(CH 2 ) 2 ] 2 X (X = O, S), 1,9‐bis(benzimidazol‐2‐yl)‐2,5,8‐trithianonane, 1,11‐bis( N ‐methylbenzimidazol‐2‐yl)‐3,6,9‐trithiaundecane, 1,11‐bis(2‐benzimidazol‐2‐yl)‐6‐oxo‐3,9‐dithiaundecane, 2‐(2‐pyridyl)benzothiazole, 2,6‐bis(benzothiazol‐2‐yl)pyridine, 2‐(2‐pyridyl)‐ N ‐methylbenzimidazole, 2‐(2‐pyridylmethyl)benzimidazole and 2‐( N ‐methyl‐2‐piperidyl)benzimidazole. The compounds were characterized, where appropriate, by their mass, uv and 1 H‐nmr spectra.