N‐Nitrosation of Secondary Amines Using Supported Perchloric Acid on Silica Gel and Stereoselectivity Study of Nitrosated Products

Abstract

N‐Nitrosation of different types of secondary amines has been proceeded using supported perchloric acid on silica gel and sodiume nitrite under heterogeneous conditions. The operational system is simple and high pure products can be easily isolated with good to high yields.

Pathways for N-Nitroso Compound Formation: Secondary Amines and Beyond

“…The nature of the organic acid seems to be crucial as the employment of methanesulfonic acid alone does not lead to efficient N -nitrosation, whereas the combination of alumina with methanesulfonic acid proved effective . More sophisticated proton sources based on solid acids or inorganic salts have also been used in conjunction with sodium nitrite, including HClO 4 /SiO 2 , molybdate sulfuric acid, Mg­(HSO 4 ) 2 /wet SiO 2 , NaHSO 4 /wet SiO 2 , and Al­(HSO 4 ) 3 /wet SiO 2. …”

Synthesis and analysis of isotopically stable labeled nitrosamines as mass spectrometry standards for drug impurity quality control

“…Traditionally, nitrous acid, which is generated in situ from sodium nitrite and mineral acids, is applied as N ‐nitrosation reagent. Besides, there are plenty of other methods described, such as NaNO 2 /Oxone, 16 NaNO 2 /PhI (OAc) 2 , 17 NaNO 2 /pTSA, 18 NaNO 2 /HClO 4 ‐SiO 2 , 19 NaNO 2 /BiCl3, 20 NaNO 2 /SiO 2 /H 2 SO 4 , 21 NaNO 2 /NaHSO 4 , 22 and many more 7 . This impressive synthetical armory reflects the importance of this chemical class for the use in preparations of pesticides, lubricants, antioxidants, and anti‐thrombotic agents with vasorelaxant activity because of the release of nitric oxide 7,15 .…”

The study of stereoselectivity and mesomeric effect of N-nitrosamines via 1H NMR spectroscopy

“…In addition, nitrosamines' ability to hydrogen bond with the membrane materials facilitate their diffusion through the membrane [28]. To date, various homogeneous [29][30][31][32] and heterogeneous systems [33][34][35][36][37][38][39][40][41] are used in the preparation of N-nitrosamines.…”