HNO made-easy from photochemical cycloreversion of novel 3,5-heterocyclic disubstituted 1,2,4-oxadiazole-4-oxides

作者：Memeo Misal Giuseppe; Dondi Daniele; Mannucci Barbara; Corana Federica; Quadrelli Paolo^*

来源：Tetrahedron, 2013, 69(35): 7387-7394.

DOI：10.1016/j.tet.2013.06.067

• 1,2,4-Oxadiazole-4-oxide
• Nitrosocarbonyl intermediates
• HNO generation
• DFT calculations
• Photochemical cycloreversion

A variety of symmetric and asymmetric 3,5-heterocyclic disubstituted 1,2,4-oxadiazole-4-oxides have been prepared through cycloaddition of aromatic and heteroaromatic nitrile oxides to heteroaromatic amidoximes. A library of novel, fully characterized, 1,2,4-oxadiazole-4-oxides has been obtained as valuable precursors, upon photochemical activation, of new nitrosocarbonyl intermediates. The photochemical cycloreversion of the 1,2,4-oxadiazole-4-oxides was investigated from the computational point of view and the hydrolysis of the generated nitrosocarbonyl intermediates in water constituted the way for an easy-made HNO generation process because of the photochemical behavior of the parent compounds.

• 出版日期2013-9-2