V. Armani, C. Dell'erba, Novi Marino
Feb 3, 1997
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron
Abstract
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(diethylamino)butadiene 1 with Grignard reagents; thus the overall transformation represents a novel approach to 1,2,5-oxadiazole and 1,2,3-triazole systems via a ring-opening ring-closure strategy.