Tetrahedron

Synthetic exploitation of the ring-opening of 3, 4-dinitrothiophene. Part 7. Access to disubstituted 1, 2, 5-oxadiazole-2-oxides and 2-phenyl-2H-1, 2, 3-triazole-1-oxides

V Armani, C Dell'Erba, N Marino, G Petrillo, C Tavani

Index: Armani, Vania; Dell'Erba, Carlo; Novi, Marino; Petrillo, Giovanni; Tavani, Cinzia Tetrahedron, 1997 , vol. 53, # 5 p. 1751 - 1758

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Citation Number: 18

Abstract

1, 4-Dialkyl-and 1, 4-diaryl-2, 3-bis (hydroxyimino) butanes 7, from reduction of the corresponding 1, 4-disubstituted 2, 3-dinitro-1, 3-butadienes 2, are transformed with satisfactory yields into 3, 4-disubstituted 1, 2, 5-oxadiazole-2-oxide 5 and 4, 5-disubstituted 2- phenyl-2H-1, 2, 3-triazole-1-oxides 6. Dinitrobutadienes 2 are obtained from the reaction of 3, 4-dinitrothiophene with diethylamine and subsequent treatment of the ensuing bis ( ...