ISSN:
1434-4475
Schlagwort(e):
Chloroacetic acid chloride
;
Phenylhydrazono acetamides
;
Pyridines
;
Pyridazin-5-ylpyridinium chlorides
;
4,5-Diamino-pyridazin-6(1H)-ones
Quelle:
Springer Online Journal Archives 1860-2000
Thema:
Chemie und Pharmazie
Notizen:
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.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1007/BF00816103
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