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Benzotriazol‐1‐ylmethylammonium salts synthesis and reactivity
Author(s) -
Katritzky Alan R.,
Hughes Craig V.,
Rachwal Stanislaw
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.5570260614
Subject(s) - chemistry , moiety , substituent , alkyl , reagent , methylene , deuterium , ammonium , medicinal chemistry , reactivity (psychology) , ring (chemistry) , methylene bridge , organic chemistry , alkylation , medicine , physics , alternative medicine , pathology , quantum mechanics , catalysis
Benzotriazol‐1‐ylmethylamines on treatment with alkylating agents afford benzotriazol‐1‐ylmethylammoni‐um salts, also available from reactions of chloromethylbenzotriazole with tertiary amines. In deuterated solvents under basic conditions the methylene protons of these salts exchange with deuterium. At elevated temperatures, an alkyl group substituent migrated from the ammonium center to the benzotriazolyl N‐3. Reactions of the salts with Grignard reagents afforded various products arising from substitution of the ammonium moiety and/or from attack on the benzotriazolyl N‐3 or on the benzenoid ring.