a three-component 1,3-dipolar cycloaddition reaction of azomethine ylide for synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) derivatives

the development of multicomponent reactions (mcrs) designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. a comparative study of the synthesis of new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) ring systems by the cycloaddition of azomethine ylides generated by a decarboxylative route from sarcosine/proline and isatin with the bis-chalcone using various conditions is described. as part of our endeavor to synthesize new bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) derivatives containing two spiro carbons which often enhances the biocidal profile or may create new medicinal properties remarkably. herein we report the facile synthesis of bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) derivatives, in a highly regio- and stereoselective manner through 1,3-dipolar cycloaddition reaction of bis-dipolarophiles with the 1,3-dipole generated from isatin derivatives and secondary amino acids (l-proline or sarcosine). the structures of cycloaddition products were assigned by ir, 1hnmr, 13cnmr and mass spectral data.