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A new and improved synthesis of 6‐aryl‐1,2,4‐triazolo[4,3‐ b ]pyridazines
Author(s) -
Lieberman Daniel F.,
Albright J. Donald
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.5570250325
Subject(s) - chemistry , pyridazine , aryl , toluene , imine , acetic anhydride , acetic acid , tetrahydrofuran , condensation , ring (chemistry) , ketone , medicinal chemistry , organic chemistry , methanol , catalysis , physics , solvent , thermodynamics , alkyl
A new and improved synthesis of 6‐aryl‐1,2,4‐triazolo[4,3‐ b ]pyridazines is described. This methodology provides the title compounds under mild conditions and in high yields. The first step comprises the condensation of an aryl methyl ketone with a 4‐amino‐1,2,4‐triazole in toluene heated at reflux. The second step involves the condensation of that imine and t ‐butoxybis(dimethylamino)methane in tetrahydrofuran at ambient temperature. The third step constitutes the pyridazine ring closure to the title compounds in acetic acid heated at reflux.