Synthesis of methylene-bis(1-oxy-3,3-dialkyl-1-triazene 2-oxides) and their analogs

Calcium Dialkylamine Diazeniumdiolates: Synthesis, Stability, and Nitric Oxide Generation

“…A solution of N -methyl-1-phenylmethanamine (0.67 mL, 5.2 mmol, 1 equiv), Ca­(OH) 2 (231 mg, 3.12 mmol, 0.6 equiv), and 3.5 mL of degassed DI H 2 O was charged with 60 psi of nitric oxide and stirred under pressure at room temperature for 100 h to give 964.7 mg (93%) of the corresponding calcium salt as a white solid. Spectral data matches with the reported data. , 1 H NMR (500 MHz,CD 3 OD): 7.18–7.42 (m, 10 H), 4.15 (s, 4H), 2.83 (s, 6H). 13 C­{1H} NMR (125 MHz,CD 3 OD): 129.1, 127.8, 127.3, 126.8, 59.1, 41.7.…”

“…1 H NMR (500 MHz,CD 3 OD): 3.02 (s, 12 H). 13 Calcium (Benzamidinium)diazen-1-ium-1,2-diolate (20). A solution of benzamidine (624.8 mg, 5.2 mmol, 1 equiv), Ca(OH) 2 (231 mg, 3.12 mmol, 0.6 equiv), and 3.5 mL of degassed DI H 2 O was charged with 60 psi of nitric oxide and stirred under pressure at room temperature for 100 h to give 855 mg (83%) of the corresponding calcium salt as a white solid.…”

“…The benzyl methyl amine sodium diazeniumdiolate 10 has been previously synthesized in 65% yield. 19,20 With our improved calcium salt method, we were able to synthesize the calcium diazeniumdiolate 11 in 93%. The more electron rich arenes, such as 4-tert-butylbenzylamine were also more nucleophilic and provided the corresponding calcium diazeniumdiolate salts in high yields.…”

Synthesis of 1-(N-nitropyrazolyl)-1Н-tetrazoles – a new type of heteronuclear N-nitropyrazole derivatives

“…18 One of the current trends in the chemistry of exogenous NО donors 19 is the synthesis of hybrid molecules 20 that may combine the ability to release NO with other types of biological activity. [21][22][23][24][25][26][27][28] Of particular interest among such compounds is a fairly rare type of heteronuclear hybrid molecules [29][30] consisting of a five-membered aromatic heterocycle linked to a N-nitropyrazole core.…”