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Chemistry of α‐(benzotriazol‐l‐yl)alkylpyridines. Unusual nucleophilic attack at c‐3a of the benzotriazolyl ring
Author(s) -
Katritzky Alan R.,
Yao Guowei,
Rachwal Stanislaw
Publication year - 1994
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.5570310411
Subject(s) - chemistry , benzotriazole , electrophile , medicinal chemistry , pyridine , reagent , nucleophile , nucleophilic substitution , alkyl , ring (chemistry) , halide , phosphorane , alkylation , carbon disulfide , wittig reaction , disulfide bond , organic chemistry , catalysis , biochemistry
Abstract Lithiation of 2‐, 3‐ and 4‐[α‐(benzotriazol‐l‐yl)methyl]pyridines with butyllithium followed by reactions with electrophiles (alkyl halides, aldehydes, ethyl benzoate and diphenyl disulfide) gave the corresponding α‐sub‐stituted derivatives in good yields. Repetition of the reaction sequence allowed substitution of the second α‐proton by an electrophile. 2‐[α‐(Benzotriazol‐l‐yl)‐α‐(phenylthio)pentyl]pyridine thus obtained gave an unusual attack of the Grignard reagents at C‐3a of the benzotriazole system on treatment with arylmagnesium bromides.