146692-13-9Relevant articles and documents
Reactions of Tetrasulfur Tetranitride with Aryl Dibromomethyl Ketones: One-pot Synthesis of 3-Aroylformamido-4-aryl-1,2,5-thiadiazoles and their Reactions
Kim, Kyongtae,Cho, Jaeeock,Yoon, Sung Cheol
, p. 253 - 260 (2007/10/02)
Heating of Dibromomethyl aryl ketones with tetrasulfur tetranitride (S4N4) at 115 deg C without a solvent gave 3-aroylformamido-4-aryl-1,2,5-thiadiazoles 8 as major products (12-71percent) and 3,5-diaroyl-1,2,4-thiadiazoles 2 as minor products in certain cases.The structures of compounds 8 were determined based on the X-ray analysis of 3-benzoylformamido-4-phenyl-1,2,5-thiadiazole 8a and comparison with an authentic sample of compound 8a, as well as all the spectroscopic and analytical data of compounds 8.Oxidation of compounds 8 with m-chloroperbenzoic acid in chloroform at room temperature gave compounds 2 (0-66percent), whereas reduction of compounds 8 with sodium boranuide in a mixture of chloroform-ethanol at room temperature gave 3-amino-4-aryl-1,2,5-thiadiazoles 10 (71-93percent).Treatment of 3-(3-nitrobenzoylformamido)-4-(3-nitrophenyl)-1,2,5-thiadiazole 8d with either sodium hydroxide in aqueous p-dioxane at reflux or sodium hydride in chloroform at room temperature gave 3-amino-4-(3-nitrophenyl)-1,2,5-thiadiazole 10d in 56 and 80percent yield, respectively.
