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Pyridazines with heteroatom substituents in position 3 and 5. 2 . Regioselective introduction of mercapto groups in pyridazines
Author(s) -
Olesen Preben H.,
Kappe Thomas,
Becher Jan
Publication year - 1988
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.5570250621
Subject(s) - chemistry , regioselectivity , heteroatom , halogen , medicinal chemistry , nucleophile , nucleophilic substitution , pyridazine , stereochemistry , ring (chemistry) , organic chemistry , alkyl , catalysis
The nucleophilic substitution of halogen in 3,5‐dichloro‐6‐phenylpyridazine 1 , 5‐chloro‐2‐methyl‐6‐phenylpyridazin‐3(2 H )‐one 13 as well as in 3‐chloro‐2‐methyl‐6‐phenylpyridazin‐5(2 H )‐one 14 with methoxy, ethoxy and the 2‐methyl‐2‐propanethiolate anion is described. In the last type of compounds the t ‐butylthio groups can be eliminated regioselectively with Lewis acids, resulting in the formation of monomercapto and mono‐thiopyridazines.