Synthese neuartig substituierter Pyridazin-6(1H)-one

Summary Arylhydrazono acetamides1 react with chloroacetic acid chloride to give N-chloroacetyl derivatives2. Subsequent reaction with pyridines followed by ring closure yield 1-(4-amino-6-oxo-pyridazin-5-yl)-pyridinium chlorides3. Analogously, 1-(6-oxo-pyridazin-5-yl)-pyridinium chloride (5) and 6-oxo-5-pyridinio-pyridazin-4-olate (4) are formed from phenylhydrazono derivatives and pyridine. Treatment of3 and4 with hydrazinium hydrate gives 4,5-diamino-6-oxo-pyridazin-3-carbohydrazides6 and 5-amino-4-hydroxy-pyridazin-6(1H)-one (8). An analogous ring cleavage of3e and5 gives rise to 4,5-diamino- and 5-amino-pyridazin-6(1H)-ones7. On treatment of the pyridinium salts3 with caustic soda in water, nucleophilic addition of the amino group to the pyridinium ring takes place and stable dehydrated products9 are isolated.

Herrn Professor Dr. Fritz Sauter zum 65. Geburtstag gewidmet