Premium
Heterocyclic‐fused benzopyrans as cannabinoid analogues
Author(s) -
Press Jeffery B.,
Birnberg Gary H.
Publication year - 1985
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.5570220270
Subject(s) - chemistry , formylation , methylhydrazine , phenylhydrazine , benzopyrans , hydrazine (antidepressant) , ring (chemistry) , hydroxylamine , cannabinoid , diazepine , organic chemistry , pyrimidine , medicinal chemistry , stereochemistry , biochemistry , receptor , chromatography , catalysis
A series of A‐ring heterocyclic analogues of tetrahydrocannabinol were investigated. Chromanones 1a and 1b were functionalized by formylation with base and ethyl formate to give 6a and 6b. These formylketones were reacted with hydrazine, and Phenylhydrazine to give pyrazoles 7a,b,e , and f , respectively. When 6a and 6b were reacted wtih methylhydrazine, mixtures of methyl isomers 7c and 8a and 7d and 8b formed in a ratio of 1:2.5. Isoxazoles 10a and 10b formed similarly when hydroxylamine was used as the condensing agent. Attempts to prepare the pyrimidine derivatives 11 were thwarted by the rearrangements of 6a and 6b to chromenones 12a and 12b.