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A convenient synthesis of 3‐formyl‐2‐oxo‐1,2‐dihydroquinoxaline chlorophenylhydrazones: Novel tautomeric equilibria between hydrazone imine and diazenyl enamine forms with long‐range pSSrototropy
Author(s) -
Kurasawa Yoshihisa,
Yamazaki Kaoru,
Tajima Setsuko,
Okamoto Yoshihisa,
Takada Atsushi
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.5570230359
Subject(s) - tautomer , chemistry , enamine , hydrazone , imine , medicinal chemistry , organic chemistry , stereochemistry , catalysis
3‐Formyl‐2‐oxo‐1,2‐dihydroquinoxaline chlorophenylhydrazones 4a‐c were synthesized from the reactions of 3‐methyl‐2‐oxo‐1,2‐dihydroquinoxaline 3 with chlorophenyl diazonium salts, and 4b,c were found to exhibit the tautomeric equilibria between the hydrazone imine and diazenyl enamine forms in the dimethylsulfoxide solutions.