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Reactions of Diethyl [(3‐Bromomethyl‐2‐Thienyl)‐Methylene]Propanedioate with Hydrazines: Syntheses of Dihydropyridazines, Pyridazines and O‐Dimethylaminomethylarenecarbonitriles
Author(s) -
Sha ChinKang,
Tsou ChiuPeng
Publication year - 1991
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199100030
Subject(s) - chemistry , diethyl malonate , hydrazine (antidepressant) , methylene , medicinal chemistry , organic chemistry , chromatography , catalysis
Facile syntheses of dihydropyridazines, pyridazines, and o ‐dimethylaminomethylarenecarbonitriles have been achieved by the retro‐malonate addition reaction. Bromoalkylidenemalonates 1,7, and 10 were treated with hydrazine to give dihydropyridazines 4, 8, and 11 in quantitative yields. DDQ or air oxidation of 4, 8, and 11 gave pyridazines 5, 9, and 12, Alternatively, treatment of 1, 7, and 10 with 1,1‐dimethylhydrazine afforded o ‐dimethylaminomethylarenecarbonitriles 6,13, and 14 in good yields.