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Pyridazines, LX. Telesubstitution and Dismutation Reactions in the Series of Phenyl‐3‐pyridazinylmethane Derivatives
Author(s) -
Heinisch Gottfried,
Huber Thierry
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920105
Subject(s) - chemistry , pyridazine , substituent , yield (engineering) , series (stratigraphy) , nucleus , medicinal chemistry , materials science , metallurgy , biology , microbiology and biotechnology , paleontology
Abstract Reactions of 3‐α‐chlorobenzylpyridazine ( 4 ) with alkoxides have been found to yield 6‐substituted or 4‐substituted 3‐benzylpyridazines ( 7a – c , 8a – c ) rather than the usual ethers ( 6a–c ). Introduction of an electron‐donating substituent into the 6‐position of the pyridazine nucleus of 4 has been shown to suppress such telesubstitution processes. With phenyl‐3‐pyridazinylmethanol ( 3 ), thermally induced dismutation affording 3‐benzylpyridazine ( 17 ) and 3‐benzoylpyridazine ( 11 ) has been observed.