FeCl3‐Catalyzed [3+2] Cycloaddition Reaction: A Mild Synthetic Approach to Spirooxindolo‐2‐iminothiazolidine Scaffolds. Issue 10 (11th March 2020)

• Record Type: Journal Article
• Authors: Bhandari, Sonal; Sakla, Akash P.; Shankaraiah, Nagula
• Is Part Of: ChemistrySelect. Volume 5:Issue 10(2020)
• Page Start: 2886
• Page End: 2891
• Publication Date: 2020-03-11
• Subjects: C−N/C−S bond formation -- cycloaddition -- isothiocyanates -- ring expansion -- spiro-oxindole aziridine.; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201904397
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A facile one‐pot [3+2] cycloaddition reaction for the synthesis of diversely substituted spirooxindolo‐2‐iminothiazolidine scaffolds has been accomplished by employing FeCl3 as catalyst. This reaction proceeds via Lewis acid‐mediated activation of spiro‐oxindole aziridines to generate a 1, 3‐dipole which undergoes intramolecular cycloaddition with different aryl/alkyl isothiocyantes. The present method offers atom economy, broad substrate scope, good to moderate yields, and wide functional group tolerance. In addition, one of the representative structures was confirmed by single X‐ray crystallography analysis. Abstract : *A facile method towards the synthesis of spiro[indoline‐3, 5′‐thiazolidin]‐2‐one derivatives via a spiro‐aziridine ring‐opening followed by cyclization has been developed. It is an efficient and sustainable approach for the construction of C−N and C−S bonds.