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Potential psychotropic agents. 7‐Chloro‐9‐phenyl‐3,3‐diethyl‐3 H ‐pyrazolo‐[5, 1‐ b ]quinazolin‐10‐ium‐2‐olate and 9‐Chloro‐2,3,4,5‐tetrahydro‐1‐methyl‐3,3‐diethyl‐7‐phenyl‐1 H ‐benzo‐1,5,6‐triazonine‐2,4‐dione
Author(s) -
Orzalesi Giovanni,
Selleri Renato,
Vittory Rodolfo Landi,
Innocenti Franco,
Grandolini Giuliano
Publication year - 1977
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.5570140505
Subject(s) - chemistry , derivative (finance) , mesoionic , hydrazone , hydrolysis , medicinal chemistry , stereochemistry , organic chemistry , financial economics , economics
2‐Amino‐5‐chloro‐α‐phenylbenzylidene hydrazone ( 1 ) or its methyl derivative 2 or acetyl derivative 10 react with diethylmalonic esters to give the corresponding malonyl derivatives 3, 4 and 8 . These esters were hydrolyzed to the acids 5 and 6 . Treating 5 with dehydrating agents the mesoionic compound 7‐chloro‐9‐phenyl‐3,3‐diethyl‐3 H ‐pyrazolo[5,1‐ b ]quinazolin‐10‐ium‐2‐olate (14) was obtained, while the methyl derivative 6 afforded the desired 9‐chloro‐2,3,4,5‐tetrahydro‐1‐methyl‐3,3‐diethyl‐7‐phenyl‐1 H ‐benzo‐1,5,6‐triazonine‐2,4‐dione ( 17 ). Some derivatives of these compounds were also described. The structures of the new compounds were confirmed by an alternative synthesis and by mass and prnr spectral data.