Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies of the Synthesis of Furan Compounds. XXIII. Cyclization Derivatives of 5-Nitro-2-furimidoylhydrazine
Ichiro HiraoYasuhiko KatoTsunetoshi HayakawaHiromichi Tateishi
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1971 Volume 44 Issue 3 Pages 780-784

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Abstract

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.

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