Understanding the spontaneous formation of pyridofuroxan from 2-azido-3-nitropyridine: A theoretical evaluation

Publication date: Available online 7 March 2019Source: Computational and Theoretical ChemistryAuthor(s): Sarai Vega-Rodríguez, Rogelio Jiménez-Cataño, Elisa LeyvaAbstractPyridofuroxans are analogous to benzofuroxans; they present similar properties and may be synthesized in similar ways. However, when they are prepared from o-nitropyridinazides, they do not need energy to be synthesized, in contrast to benzofuroxans which require heat or light. In order to understand this phenomenon, a DFT study about the mechanism of pyridofuroxan formation from a series of substituted o-nitropyridinazides (2-azido-3-nitropyridines) was performed. The results suggest that spontaneous formation of pyridofuroxans at room temperature is possible when o-nitropyridinazide is protonated at the pyridinic nitrogen.Graphical abstract

Source: Computational and Theoretical Chemistry - March 7, 2019 Category: Chemistry Source Type: research