September 10, 2025The Journal of Organic Chemistry

Regio- and Stereospecific Nucleophilic C3-Azidation of Spiroaziridine Oxindoles: Synthesis of Enantiopure 3-Azido- and 3-Triazole-2-oxindoles

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Authors

AMAnanda Shankar MondalSanjay Gandhi Post Graduate Institute of Medical Sciences ABAnkita BiswasSanjay Gandhi Post Graduate Institute of Medical Sciences AJAnimesh JanaIndian Institute of Science Education and Research, Bhopal

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Implication

This method achieves regio- and stereospecific nucleophilic azidation in spiroaziridine oxindoles, suggesting enhanced enantioselectivity and robust yields.

Key Points

The method shows over 99% enantioselectivity and excellent yields in synthesizing 3-azido oxindoles.
Using trimethylsilyl azide under catalyst-free conditions enables robust and scalable production.
3-Azido oxindoles can be synthesized into 3-amino- and 3-triazole derivatives through Staudinger reduction and click chemistry.
The process opens pathways to link oxindole units to clinically relevant drugs like norethindrone.

Cite This Study

Mondal et al. (2025) studied this question.

synapsesocial.com/papers/68c243acb210217d647a87f4 https://doi.org/10.1021/acs.joc.5c00985

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Implication

This method achieves regio- and stereospecific nucleophilic azidation in spiroaziridine oxindoles, suggesting enhanced enantioselectivity and robust yields.

Regio- and Stereospecific Nucleophilic C3-Azidation of Spiroaziridine Oxindoles: Synthesis of Enantiopure 3-Azido- and 3-Triazole-2-oxindoles

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Implication

Key Points

Cite This Study

Regio- and Stereospecific Nucleophilic C3-Azidation of Spiroaziridine Oxindoles: Synthesis of Enantiopure 3-Azido- and 3-Triazole-2-oxindoles

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Key Points

Cite This Study

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