1226859-15-9Relevant articles and documents
Azodicarhoxamides vs. azodicarboxylates in reactions against thioisomuenchnones: 1,3-dipolar cycloaddition or nucleophilic addition?
Sanchez, Barbara,Lopez, Ignacio,Light, Mark E.,Silvero, Guadalupe,Bravo, Jose Luis
scheme or table, p. 1648 - 1652 (2010/06/16)
This communication presents the first study on the use of azodicarboxamides against mesoionic heterocycles as 1,3-dipoles. The reactions yield thioureido compounds. Their formation could be explained, on the basis of experimental results and preliminary theoretical calculations, by a nucleophilic addition followed by rearrangement; however, a formal 1,3-dipolar cycloaddition and subsequent fragmentation and rearrangement of the transient cycloadducts could not be ruled out. Reactions are carried out in refluxing toluene and are complete in 90-240 min. Structural elucidation of the products is based on single-crystal X-ray analysis, as well as other spectroscopic data and 2D-NMR correlations.