Aminopyrimidines as Electron-Rich Azadienes: Extension of the Synthetic Potential of Hetero Diels-Alder Reactions under Acidic Conditions
31 December 2001 (online)
By addition of a catalytic amount of a strong acid and selection of the appropriate solvent, the cycloaddition reactions of dimethyl acetylenedicarboxylate (DMAD) to 6-aminopyrimidine derivatives drastically changed their course leading to new products, pyrrolo[3,4-c]pyridines, which were different from those obtained in the absence of acid. This change was interpreted on the basis of acid interception of the non-isolable adducts formed by initial hetero Diels-Alder cycloaddition between the reactants.
hetero Diels-Alder reactions - glycosides - heterocycles - pyrimidines - tandem reactions