β-nitro- and β-bromo-β-nitrostyrenes in the reactions with aminonitroguanidine

Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)ethenes

“…Absorbance at 1426-1440 and 1313-1338 cm -1 was assigned to the NNO 2 group stretching. IR spectral features of compounds XI-XIII were in line with those of the structurally similar compounds prepared previously [5,6].…”

“…The spectral data of X and XV coincided with those of the same compounds synthesized independently [5].…”

“…Strong absorption bands at λ max of 328-337 nm (ε = 28000-33000 L mol -1 cm -1 ) observed in electronic absorption spectra of XI-XIII were characteristic of chromophore system of such compounds [5,7]. 1 H NMR spectrum of a mixture of XIV and XV contained the proton signals of the both compounds.…”

“…The precipitated crystals were filtered off, washed sequentially with water, ethanol, and diethyl ether, and dried in air to yield 0.16 g of a mixture of XIV and XV in the ratio of 1 : 1 ( 1 H NMR). After recrystallization from ethanol, only compound XV was isolated, mp 241-243°C (ethanol-water, 2 : 1) (mp 240-242°C [5]). Found N, %: 32.57.…”

“…Previously, we studied the reaction of 2-aryl-1nitro-and 1-bromo-1-nitroethenes with 1-amino-2-nitroguanidine, yielding the amination products: 1nitro-and 2-aryl-1-bromo-1-nitro-2-(2-nitroguanidinoamino)ethanes [5]. In the presence of basic catalyst or upon prolonged refluxing the adducts derived from gem-bromonitrostyrenes were cleaved to form Narylmethylidene-N-(2-nitroguanidino)amines.…”