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Expanding the Limits of Organic Energetic Materials: High-Performance Alliance of 1,3,4-Thiadiazole and Furazan Scaffolds

“…The title compound was synthesized using a previously described procedure. 49 A mixture of 3-amino-4-cyano-1,2,5-oxadiazole (6.1 g, 5.5 mmol), thiosemicarbazide (5.5 g, 6.0 mmol), and trifluoroacetic acid (20 mL) was refluxed for 5 h on an oil bath, cooled to 20 °C, and then poured into 50 mL of a 30% ammonia solution. The gray precipitate was filtered off, washed with water, and dried in air: yield 7.6 g (75%); gray solid; 1 H NMR (DMSO-d 6 , 300 MHz) δ 7.94 (s, 2H, NH 2 ), 6.52 (s, 2H, NH 2 ).…”

“…All other data were consistent with those previously published. 49 Synthesis of 4-(5-Amino-1,3,4-thiadiazol-2-yl)-3-nitro-1,2,5oxadiazole (3). (NH 4 ) 2 S 2 O 8 (1.47 g, 6.5 mmol) was added to a stirred 75% H 2 O 2 solution (13 mL) at 0 °C.…”

A facile synthesis and microtubule-destabilizing properties of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines

“…To date, there are three main routes towards 9 described in the literature (Scheme 1). Route A [17] involves treatment of (un)substituted o-phenylenediamines 3 with carbimidate 2 [18] easily accessible from the amidoxime 1. Route B [6] is based on recyclization of 5 upon heating with o-phenylenediamines 3 in acetic acid.…”

A Novel Mild Method for the Synthesis of 3-Amino-4-(5-aryl-1H-1,2,4-Triazol-3-yl)Furazans

“…[3][4][5][6] The most general (with seven examples) method for constructing molecules with this combination of azoles is the high-temperature (200-230°C) cyclocondensation of N'-acylated furazan carbohydrazonamides (amidrazones). [7][8][9] A few of individual approaches for accessing a particular derivative has been described. 1,4,10 The published methods afford only a limited group of (1,2,4-triazol-3-yl)furazans and use either very harsh reaction conditions or highly toxic reagents, that limits the widespread use of these compounds.…”