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Synthesis of some benzimidazole‐, pyridine‐ and imidazole‐derived chelating agents
Author(s) -
Wahlgren Curtis G.,
Addison Anthony W.
Publication year - 1989
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.5570260303
Subject(s) - benzimidazole , chemistry , imidazole , pyridine , hydrochloric acid , denticity , chelation , hydrochloride , aqueous solution , medicinal chemistry , organic chemistry , combinatorial chemistry , metal
Procedures are described for the preparation of various bidentate and potentially tridentate chelating agents. These incorporate pyridyl, benzimidazole, imidazole or phenolic moieties. Phillips condensations of carboxylic acids with o ‐phenylenediamines were carried out in 4 M hydrochloric acid. Syntheses are reported for 2, 6‐bis( N ′‐methylimidazol‐2′‐ylthiomethyl)pyridine, 2, 6‐bis(benzimidazol‐2′‐ylthiomethyl)pyridine, 2‐(4′‐piperidyl)benzimidazole, 2‐(3′‐piperidyl)benzimidazole, 2‐(3‐ N ′‐methylpiperidyl)benziinidazole, 2‐(3‐ N ′‐methylpiperidyl)‐ N ‐methylbenzimidazole, 2‐(2′‐hydroxybenzyl)benzimidazole and 2‐(2′‐hydroxyben‐zyl) N ‐methylbenzimidazole. The compounds were characterized where appropriate by their mass, uv, and 1 H‐nmr spectra. 2‐(2′‐Hydroxybenzyl)benzimidazole hydrochloride acts as a gelling agent in aqueous solution.