Green Synthesis of Spirooxindole-pyrrolidine/Piperidine Fused Nitrochromane: One Pot Three Component Stereo and Regioselective Cycloaddition

Title:Green Synthesis of Spirooxindole-pyrrolidine/Piperidine Fused Nitrochromane: One Pot Three Component Stereo and Regioselective Cycloaddition

Volume: 13 Issue: 1

Author(s): Sabita Nayak, Sambita K. Mishra, Sujitlal Bhakta, Pravati Panda, Nilofar Baral, Seetaram Mohapatra, Chandra S. Purohit and Pardhasaradhi Satha

Affiliation:

Keywords: Isatin, 1, 3-dipolar cycloaddition reaction, heterocycles, spirooxindole, piperidine, pyrrolidine.

Abstract: Background: Now a day’s green synthesis for multicomponent reactions is a powerful tool for construction of five membered/six membered heterocyclic ring systems. The synthesis of regio and stereoselective complex architectural motifs following 1,3-dipolar cycloaddition reactions via ecofriendly methods are well reported. The synthesis of pyrrolidine/piperidine based heterocycles has been the center of attraction because of their pronounced biological activities.

Methods: The present methodology deals with one pot three component cycloaddition reaction of isatin based azomethine ylide and substituted nitrochromene to synthesize new spirooxindole-pyrrolidine/piperidine fused nitrochromanes in refluxing ethanol within 2 hr.

Results: A series of new spirooxindole-pyrrolidine/piperidine fused nitrochromanes were synthesized in good to excellent yield (78-89%) via one pot three component cycloaddition reactions. The obtained products were isolated in good yield by simple filtration. All the synthesized compounds were well characterized (¹H, ¹³C, Mass and M.P). The regio/ stereochemical results were ascertained by X-ray crystallographic study.

Conclusion: We have developed an ecofriendly method to synthesize twelve new and novel spirooxindolepyrrolidine/ piperidine fused nitrochromanes via one pot three component 1,3-dipolar cycloaddition reaction in nontoxic solvent in a shorter time. It offers several advantages such as regio/stereoselective synthesis of spirooxindolepyrrolidine/ piperidine fused nitrochromanes, shorter reaction time, mild reaction conditions, simple and environmentally friendly operational procedure.

Cite this article as:

Nayak Sabita, K. Mishra Sambita, Bhakta Sujitlal, Panda Pravati, Baral Nilofar, Mohapatra Seetaram, S. Purohit Chandra and Satha Pardhasaradhi, Green Synthesis of Spirooxindole-pyrrolidine/Piperidine Fused Nitrochromane: One Pot Three Component Stereo and Regioselective Cycloaddition, Letters in Organic Chemistry 2016; 13 (1) . https://dx.doi.org/10.2174/1570178612666151030213735