Journal of Heterocyclic Chemistry · 1966 · 20 citations · 9 references
Natural SciencesChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisPyrazine ChemistryPyrazole ChemistryPyridazine Chemistry
Abstract Pyrazino[2,3‐ d ]pyridazine (I) was synthesized by two different routes. 5, 8‐Dihydroxy‐pyrazino[2, 3‐ d ]pyridazine (IV) was converted to 5, 8‐dichloropyrazino[2, 3‐ d ]pyridazine (V) and 5, 8‐dibromopyrazino[2, 3‐ d ]pyridazine (Va). When V was treated with various benzyl mercaptans and alkoxides the corresponding disubstituted derivatives were obtained. Compound V when allowed to react with aromatic amines gave 5, 8‐bisamino‐pyrazino[2,3‐ d ]pyridazines, however, with aliphatic amines only mono substituted products were obtained substituted in the 8‐position. The reaction of pyrazine‐2, 3‐dinitrile with hydrazine gave 5, 8‐diaminopyrazino[2, 3‐ d ]pyridazine (X).
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William D. Guither, Donald G. Clark, Raymond N. Castle · Journal of Heterocyclic Chemistry · 1965 · 36 citations