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Beiträge zur Chemie von Tetraketonen, III Synthese und einige Reaktionen des 1,6‐Bis( p ‐hydroxyphenyl)‐1,3,4,6‐hexantetrons
Author(s) -
Kovač Spomenka,
Rapić Vladimir,
Laćan Marijan
Publication year - 1984
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198419841016
Subject(s) - chemistry , hydrazine (antidepressant) , triethylamine , sodium ethoxide , phenylhydrazine , quinoxaline , medicinal chemistry , isocyanate , condensation , polymer chemistry , organic chemistry , ethanol , chromatography , polyurethane , physics , thermodynamics
Contributions to the Chemistry of Tetraketones, III. ‐ Synthesis and Some Reactions of 1,6‐Bis( p ‐hydroxyphenyl)‐1,3,4,6‐hexanetetrone Condensation of p ‐hydroxyacetophenone and diethyl oxalate in the presence of sodium ethoxide gave the tetraketone 3 which can be cyclized with o ‐phenylenediamine, hydrazine, or phenyl‐hydrazine to yield the quinoxaline 1 or the 3,3′‐bipyrazolyl derivatives 5 and 6 , respectively. Transformation of the p ‐hydroxyphenyl group in compounds 1 and 3 with methyl isocyanate/triethylamine gave the corresponding carbamates 2 and 4 . By condensation of 4 with hydrazine or phenylhydrazine the pyrazoles 7 and 8 were prepared. Compounds 4, 7 , and 8 showed no progressive inhibitory properties against acetylcholinesterase.