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Benzocycloheptapyridines. Analogs of azatadine
Author(s) -
Halczenko Wasyl,
Shepard Kenneth L.
Publication year - 1986
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.5570230154
Subject(s) - chemistry , moiety , cyproheptadine , hydrolysis , olefin fiber , nitrile , stereochemistry , organic chemistry , catalysis , biochemistry , receptor , serotonin
Certain 3‐substituted derivatives of cyproheptadine ( 1a ) have been shown to possess potent pharmacological properties. The structural analogy between cyproheptadine and azatadine ( 2 ) prompted the preparation of 9‐substituted derivatives of 2 and its 5,6‐dehydro analog for pharmacological comparison. The 9‐cyano and 9‐trifluoromethylthio derivatives were prepared by direct displacement of the corresponding 9‐bromo compounds. Acid hydrolysis of the nitriles generated the carboxylic acids. Oxidation of the trifluoromethylthio compounds 15a and 18a gave the epoxy sulfones 19a and 19b , which could not be deoxygenated. Therefore, the trifluoromethylsulfonyl moiety was introduced prior to the formation of the exocyclic olefin.