Studies of the Synthesis of Furan Compounds. XXIII. Cyclization Derivatives of 5-Nitro-2-furimidoylhydrazine
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概要
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The reaction of 5-nitro-2-furimidoylhydrazine (I) with diacetyl or furil gave 3-(5-nitro-2-furyl)-5,6-disubstituted-1,2,4-triazine derivatives (IIa, b). Refluxing I in a large excess of ethyl orthoformate afforded 3-(5-nitro-2-furyl)-5-ethoxy-1,2,4-triazoline (III) and bis[3-(5-nitro-2-furyl)-1,2,4-triazolyl]methyl ethyl ether (IV). By heating with ethyl orthoformate, III was converted to IV. When III or IV was heated in diluted sulfuric acid, 3-(5-nitro-2-furyl)-1,2,4-triazole (V) was produced. The reactions of I with cyanogen bromide in refluxing methanol and with nitrous acid in diluted hydrochloric acid gave the corresponding 3-(5-nitro-2-furyl)-5-amino-1,2,4-triazole (VI) or -1,2,4,5-tetrazole (VIII) respectively. When heated in acetic anhydride, the VI afforded monoacetyl compound (VII), while the VIII yielded 5-(5-nitro-2-furyl)-2-methyl-1,3,4-oxadiazole (X). The structures of these compounds were discussed on the basis of their IR and NMR spectra.
- 公益社団法人 日本化学会の論文
著者
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Kato Yasuhiko
Department Of Anesthesiology Osaka Dental University
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Hirao Ichiro
Department of Chemical Engineering, Kyushu Institute of Technology
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Hayakawa Tsunetoshi
Department of Chemical Engineering, Kyushu Institute of Technology
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Tateishi Hiromichi
Department of Chemical Engineering, Kyushu Institute of Technology
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