Synthesis of Substituted Pyridazin-3-ones, 1,2-Oxazin-3-ones, and Furopyrimidines from (Arylmethylidene)furan-2(3H)-ones

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作者
T. V. Anis’kova
A. Yu. Egorova
机构
[1] Chernyshevskii Saratov National Research State University,Institute of Chemistry
来源
Russian Journal of Organic Chemistry | 2018年 / 54卷
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摘要
Reactions of 5-substituted 3-(arylmethylidene)furan-2(3H)-ones with hydrazine hydrate, hydroxylamine, and guanidine involved opening of the furanone ring. Their hydrazinolysis under mild conditions afforded acyclic 4-oxoalkanoic acid hydrazides which underwent heterocyclization to substituted pyridazinones in boiling ethanol. The presence of an alkyl substituent in the 5-position of the initial furanone favored heterocyclization with the formation of pyrazolidinone derivatives. The reactions of 3-(arylmethylidene)furan-2(3H)-ones with hydroxylamine and guanidine also produced new six-membered heterocycles, 2H-1,2-oxazin-3(4H)-ones and 4,6-disubstituted 3,4-dihydrofuro[2,3-d]pyrimidin-2-amines, respectively.
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页码:1389 / 1394
页数:5
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