56526-34-2Relevant academic research and scientific papers
REACTIONS DE CYCLOADDITION DIPOLAIRE-1,3 DES THIAZOLONES ET DES SELENAZOLONES MESOIONIQUES AVEC L'ACETYLENE DICARBOXYLATE DE METHYLE-II
Baudy, M.,Robert, A.,Guimon, C.
, p. 2129 - 2138 (2007/10/02)
Mesoionic thyazolones and selenazolones react with dimethyl acetylene dicarboxylate to give thiophenes or pyridones.We show that the reactivity of the mesoionic thiazolones towards dimethyl acetylene dicarboxylate may be explanied by second order perturbation theory, limited to frontier orbitals.The influence of the temperature and of the nature of the substituants on the evolution of the primary cycloadduct can be explained by competition between a retro Diels-Alder rection giving a thiophene and a desulfurisation or a deselenurisation giving a pyridone.
QUATERNARISATION DE L'ATOME D'AZOTE DE SYSTEMES TAUTOMERES DE LA SERIE DES OXO-4 THIAZOLES. CYCLOADDITIONS DIPOLAIRES 1,3 DES THIAZOLES MESOIONIQUES FORMES IN SITU
Robert, A.,Ferrey, M.,Marechal, A. Le
, p. 1571 - 1578 (2007/10/02)
4-Hydroxythiazoles and N-acylimino 4-thiazolidinones show similar tautomeric behaviour to azlactones.However, the mechanism of their reaction with dimethylacetylenedicarboxylate or with ethyl vinyl ether differs fundamentally.In the thiazole series, the first step is the quaternization of the nitrogen atom.The mesoionic thiazole intermediate is then trapped by a second molecule of the dipolarophile.
