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Synthesis of 3‐aryl‐6 H ‐isoxazolo[3,4‐ d ]pyrazolo[3,4‐ b ]pyridines and 3‐aryl‐6 H ‐isoxazolo[5,4‐ d ]pyrazolo[3,4‐ b ]pyridines
Author(s) -
Shutske Gregory M.,
Huger Francis P.
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.5570250301
Subject(s) - chemistry , aryl , stereochemistry , d 1 , organic chemistry , biochemistry , alkyl , receptor
The synthesis and characterization of a number of 3‐aryl‐6 H ‐isoxazolo[3,4‐ d ]pyrazolo[3,4‐ b ]pyridines and 3‐aryl‐6 H ‐isoxazolo[5,4‐ d ]pyrazolo[3,4–6]pyridines from common precursors, 5‐benzoyl‐4‐chloro‐1 H ‐pyrazolo‐[3,4‐ b ]pyridines, has been described. The structures were determined by unambiguous chemical synthesis and by isolation and 13 C nmr analysis of some key, isolated, intermediates. The ability of these compounds to displace [3 H ]flunitrazepam from CNS binding sites was also observed.