4-Acetyl-1-(R-benzylidene)-3-(5-nitro-2-furfuryl)thiosemicarbazides - Carriers of Synthones for Obtaining Thiazole and Triazole Rings

Article abstract of DOI:10.1007/BF00755702

The corresponding thiosemicarbazonium salts, which form 4-acetyl- and 2,4-diacetyl-1-benzylidene-3-(5-nitro-2-furfuryl)thiosemicarbazides with acetic anhydride, were obtained by the reaction of 5-nitrofurfuryl bromide with 1-benzylidenethiosemicarbazides.Under the influence of bases the monoacetylated derivatives undergo cyclization to the corresponding 2-benzylidenehydrazino-5-(5-nitro-2-furyl)thiazoles.Intramolecular cyclization of the monoacetylated products to 3-methyl-5-<(5-nitro-2-furfuryl)thio>-1,2,4-triazole, which is accompanied by the elimination of the corresponding benzaldehyde, occurs in the presence of hydrochloric acid.