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Bicyclic [b]-heteroannulated pyridazine derivatives. 10. Acid cleavage of some beta-keto esters in the reaction with 4,4-dimethyl- and 4-phenyltetrahydropyridazine-3,6-dione 3-hydrazones

4,4-Dimethyltetrahydropyridazine-3,6-dione 3-hydrazone (1) reacted with beta-keto esters in refluxing ethanol to give the acid cleavage products: 7,8-dihydro-3,8,8-trimethyl-triazolo[4,3-b]pyridazin-6(5H)-one (7) and esters 9. The yield of the reaction in most cases was nearly quantitative. At room temperature mostly the simple condensation products 4 were isolated. In analogous reactions, 4-phenyltetrahydropyridazine-3,6-dione 3-hydrazone (2) was found to be much less reactive. The hydrazone-ester condensation products 4 and some 5 were converted into the corresponding pyrazolylpyridazine derivatives 10 and 11, respectively, by heating above their melting points; the formation of 7 was noted in the reactions with 4. The results support the concept of different tautomeric preferences in 1 and 2.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H4097O – PubChem