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Oxidative cyclization of n ‐methyl‐ and n ‐benzoylpyridylthioureas. Preparation of new thiazolo[4,5‐ b ] and [5,4‐ b ] pyridine derivatives
Author(s) -
Jouve Karine,
Bergman Jan
Publication year - 2003
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.5570400210
Subject(s) - chemistry , potassium ferricyanide , sodium methoxide , pyridine , bromine , pyridinium , acetic acid , medicinal chemistry , ring (chemistry) , oxidative phosphorylation , potassium , iodine , organic chemistry , methanol , biochemistry
Cyclization of N ‐methyl‐ and N ‐benzoylpyridylthioureas, prepared from the corresponding aminopy‐ridines, has been realized using various conditions. With bromine in acetic acid or potassium ferricyanide, the cyclization occurred on the nitrogen of the pyridine ring and pyridinium salts or 1,2,4‐fhiadiazolo[2,3‐ a ]pyridylidene systems were obtained. On the other hand, treatment of the thioureas with sodium methoxide in N ‐methylpyrrolidinone (NMP) led to formation of fhiazolo[4,5‐ b ] and [5,4‐ b ]pyridines, which are interesting targets for biological evaluation.