Microwave‐Assisted One‐Pot [3+2] Cycloaddition of Azomethine Ylides and 3‐Alkenyl Oxindoles: A Facile Approach to Pyrrolidine‐Fused Bis‐Spirooxindoles. Issue 5 (5th February 2019)

• Record Type: Journal Article
• Authors: Bhandari, Sonal; Sana, Sravani; Sridhar, Balasubramanyam; Shankaraiah, Nagula
• Is Part Of: ChemistrySelect. Volume 4:Issue 5(2019)
• Page Start: 1727
• Page End: 1730
• Publication Date: 2019-02-05
• Subjects: C–C/C–N bond formation -- [3+2] Cycloaddition -- green protocol -- microwave irradiation -- pyrrolidine fused-oxindole; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201802847
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: An efficient microwave‐assisted one‐pot method has been developed for the construction of pyrrolidine fused bis‐spirooxindoles through insitu generated azomethine ylide from decarboxylative condensation of isatins and primary α‐amino acids with concomitant [3+2] cycloaddition of 3‐alkenyl oxindoles. These reactions were effectively accelerated by microwave irradiation in ethanol solvent without any additives or catalyst and enable broad substrate scope, atom‐economy, eco‐friendly, and good yields. The structure and stereochemistry of pyrrolidine fused bis‐spirooxindole ring was unambiguously established by single‐crystal X‐ray analysis. Abstract : A greener one‐pot protocol has been developed for the synthesis of bis‐spirooxindoles using primary amino acids as chiral substrates in a diastereoselective manner. The reactions have been performed under microwave conditions by using ethanol as solvent without using any additives and catalyst which enables broad substrate scope, high atom economy, eco‐friendly method with good yields. The structure of one of the compounds4 i was determined by single X‐ray crystallography.