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Review
. 2023 Oct;27(5):2365-2397.
doi: 10.1007/s11030-022-10510-9. Epub 2022 Aug 4.

1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments

Fatemeh Rostami Miankooshki  1 , Mohammad Bayat  2 , Shima Nasri  1 , Narges Habibi Samet  1
Affiliations
Review

1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments

Fatemeh Rostami Miankooshki et al. Mol Divers. 2023 Oct.

Abstract

The unique therapeutic and biological characteristics of spirooxindole have led to the presentation of numerous reactions for the synthesis of spirooxindoles through 1,3-Dipolar cycloaddition of highly reactive isatin-derived azomethine ylides with activated olefins as the main tool for the formation of spirocyclic oxindoles during the last 4 years. Therefore, there is a need to highlight the recent developments in this area, along with the representative synthetic methods and relevant reaction mechanisms from 2018 to 2021. The representative synthetic methodologies were listed in four sections based on the procedure to form the azomethine ylide species including isatins and amino acids, isatin-derived α-(trifluoromethyl)imine, isatins and benzylamines, and from isatin-derived cyclic imine 1,3-dipoles.

Keywords: 1,3-Dipolar cycloaddition; Azomethine ylide; Dipolarophile; Isatin; Spirooxindole; Spirooxindole pyrrolidine.

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