Abstract
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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Original Russian Text © T.V. Anis’kova, A.Yu. Egorova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 9, pp. 1374–1379.
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Anis’kova, T.V., Egorova, A.Y. Synthesis of Substituted Pyridazin-3-ones, 1,2-Oxazin-3-ones, and Furopyrimidines from (Arylmethylidene)furan-2(3H)-ones. Russ J Org Chem 54, 1389–1394 (2018). https://doi.org/10.1134/S1070428018090208
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DOI: https://doi.org/10.1134/S1070428018090208