Transamination of Dimethylaminomethyleneoxindole

摘要

The oxindole skeleton has been found in numerous natural products and is also used as a synthetic intermediate for the preparation of numerous heterocyclic compounds with interesting biological property.In particular,3-methylene-oxindoles have been synthesized as GABAergic agents enhance benzodiazepine binding and antagonize cyclic GMP elevations,and tyrosine kinase inhibitors exhibit selectively toward different receptor tyrosine kinases.More recently,the biological importance of cyclin-dependent kinases as useful targets in cell cycle regulation has led to a considerable amount of synthetic works in oxindole-based compound.Notwithstanding the importance of this heterocyclic system,existing methods for 3-substituted oxindole synthesis are limited in their scope and generality.As a part of our program,we have an interest in preparing 3-aminomethyleneoxindole derivatives for potential biological activity.There are many reports of 3-component condensation of active methylene compounds with several amine species,such as a-aminoacids,carbamates,and ureas,in the presence of triethyl orthoformate.They include cyclohexane-l,3-dione,4-hydroxy-lH-quinolin-2-one,and 4-hydroxycoumarin.