100-75-4Relevant articles and documents
The Use of Potassium/Sodium Nitrite as a Nitrosating Agent in the Electrooxidative N-Nitrosation of Secondary Amines
Chen, Zuxing,Gao, Meng,Lu, Cuifen,Ma, Chao,Ruan, Mengyao,Wang, Feiyi,Wang, Ying,Yang, Guichun,You, Shiqi
, p. 3289 - 3293 (2021)
We report herein on the electrochemical N-nitrosation of secondary amines using widely available sodium/potassium nitrite as a nitrosating agent. This approach not only eliminates the need for using a combination of sodium/potassium and a strong acid but also has good functional group tolerance. The reaction is compatible with the late-stage modification of pharmaceutical compounds and could be conducted in gram scale with a high reaction efficiency. Preliminary mechanistic studies indicate that the N-nitrosation occurs via the anodic oxidation of KNO2 into an NO2 radical which is then transformed into an NO+ cation.
Oxone-sodium nitrite mediated N-nitrosamines formation under mild conditions from secondary amines
Gaur, Pinki,Banerjee, Shaibal
, p. 2270 - 2279 (2019)
Herein, we report an efficient synthesis of N-nitrosamines from cyclic, aliphatic, benzylic, and aromatic secondary amines via a novel straightforward, efficient, and mild chemical process using sodium nitrite and Oxone in methanol as a solvent at 0–5 °C. The demonstrated methodology accounts well for the parameters like cost-effective, short reaction time, clean and safe handling along with good to excellent yields.
Synthesis and properties of 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1-triazene 2-oxides)
Smirnov,Nikitin,Gordeev,Pokhvisneva,Ternikova,Luk’yanov
, p. 2706 - 2711 (2015)
Synthetic approach to 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1triazene 2-oxides), promising NO donors, which can release NO in living organisms was developed. Some transformations of the hydroxyethyl moiety of the synthesized compounds were studied.
The mild N-nitrosation of secondary amines with trichloro nitromethane
Demir,Mahasneh,Aksoy,Gercek
, p. 2607 - 2611 (1992)
Reaction of trichloronitromethane with secondary amine leads to the formation of corresponding carcinogeneous N-nitrosamines under mild conditions.
THE OXIDATION OF HYDROXYLAMINE BY FREMY'S SALT. PREPARATION OF N-NITROSAMINES AND TETRAZENES
Tato, M. P. Vazquez,Castedo, Luis,Riguera, Ricardo
, p. 623 - 626 (1985)
Treatment of secondary amines with Fremy's salt in aqueous sodium carbonate solution and in the presence of hydroxylamine gives a high yield of either N-nitrosamines or sym-tetrazenes.A mechanism for these conversions is proposed.
Silica chloride/NaNO2 as a novel heterogeneous system for the nitrosation of secondary amines under mild conditions
Zolfigol, Mohammad Ali,Shirini, Farhad,Ghorbani Choghamarani, Arash
, p. 1809 - 1813 (2002)
Secondary amines can be readily converted to their corresponding nitroso derivatives with a combination of silica chloride (I), wet SiO2 and sodium nitrite in dichloromethane at room temperature with moderate to excellent yields.
Synthesis of N,N-dialkylnitramines from secondary ammonium nitrates in liquid or supercritical carbon dioxide
Kuchurov,Fomenkov,Zlotin
, p. 2058 - 2062 (2009)
An efficient explosion-proof method was developed for the preparation of N,N-dialkylnitramines by treatment of dialkylammonium nitrates with a mixture of nitric acid and acetic anhydride in the presence of ZnCl2 in liduid or supercritical carbon dioxide.
The use of Nafion-H/NaNO2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions
Zolfigol, Mohammad Ali,Habibi, Davood,Mirjalili, BiBi Fatemeh,Bamoniri, Abdolhamid
, p. 3345 - 3349 (2003)
A combination of Nafion-H and sodium nitrite in the presence of wet SiO2 was used as an effective agent for the N-nitrosation of secondary amines under mild and heterogeneous conditions in good to excellent yields.
N-nitrosation of secondary amines using p-TSA-NaNO2 as a novel nitrosating agent under mild conditions
Borikar, Sanjay P.,Paul, Vincent
, p. 654 - 660 (2010)
A combination of p-toluenesulfonic acid (p-TSA) and sodium nitrite was used as a novel effective nitrosating agent for the N-nitrosation of secondary amines to their corresponding nitroso derivatives under mild and heterogeneous conditions in moderate to excellent yields.
The reaction of peroxynitrite with morpholine (secondary amines) revisited: The overlooked hydroxylamine formation
Kirsch, Michael,Korth, Hans-Gert,Wensing, Angela,Lehnig, Manfred,Sustmann, Reiner,De Groot, Herbert
, p. 2399 - 2424 (2006)
The reaction of peroxynitrite/peroxynitrous acid with morpholine as a model compound for secondary amines is reinvestigated in the absence and presence of carbon dioxide. The concentration- and pH-dependent formation of N-nitrosomorpholine and N-nitromorpholine as reported in three previous papers ([25] [26] [14]) is basically confirmed. However, 13C-NMR spectroscopic product analysis shows that, in the absence of CO2, N-hydroxymorpholine is, at pH≥7, the major product of this reaction, even under anaerobic conditions. The formation of N-hydroxymorpholine has been overlooked in the three cited papers. Additional (ring-opened) oxidation products of morpholine are also detected. The data account for radical pathways for the formation of these products via intermediate morpholine-derived aminyl and α-aminoalkyl radicals. This is further supported by EPR-spectrometric detection of morpholine-derived nitroxide radicals, i.e., morpholin-4-yloxy radicals. N-Nitrosomorpholine, however, is very likely formed by electrophilic attack of peroxynitrite-derived N2O4. 15N-CIDNP Experiments establish that, in the presence of CO2, N-nitro- and C-nitromorpholine are generated by radical recombination. The present results are in full accord with a fractional (28±2% ) homolytic decay of peroxynitrite/peroxynitrous acid with release of free hydroxyl and nitrogen dioxide radicals.
