A Three-Component 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylide for Synthesis of New Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines) Derivatives

Subject Areas : International Journal of Bio-Inorganic Hybrid Nanomaterials

Received: 2014-08-20 Accepted : 2014-10-25 Published : 2014-10-01

Keywords: Proline, Sarcosine, Azomethine ylides, Bis-dipolarophiles, Bis-spiro-oxindolo(pyrrolizidines/pyrrolidines),

Abstract :

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.