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Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 2: 694 - 706

DOI: https://doi.org/10.6023/cjoc202406001

ARTICLES

Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols

  • Xueying Yang ,
  • Yuanshuang Xu ,
  • Xinying Zhang ,
  • Xuesen Fan
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  • Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
*E-mail: ;

Received date: 2024-06-01

  Revised date: 2024-07-15

  Online published: 2024-08-26

Supported by

National Natural Science Foundation of China(U2004189); Central Plains Science and Technology Innovation Leader Project(224200510009); Postdoctoral Research Grant in Henan Province(HN2022041)

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Abstract

A novel synthesis of C2-spiroindoline derivatives based on the cascade reaction of 2-aryl-3H-indoles with cyclo- propanols is presented. The formation of product involves Rh(III)-catalyzed aryl C(sp2)—H bond alkylation of 2-aryl- 3H-indole, which is followed by intramolecular spiroannulation. In this tandem process, cyclopropanol acts as not only an alkylating agent but also a masked nucleophile to take part in the construction of the spirocyclic scaffold. Meanwhile, air acts as an economical and sustainable oxidant to promote the regeneration of the active catalyst. By using this method, hybrid compounds containing the central scaffolds of some clinical drugs were prepared effectively. In general, this newly developed method has advantages such as easily obtainable substrates, concise synthetic procedure, excellent atom-economy, good compatibility with diverse functional groups and ready scalability.

Key words： C2-spiroindolines; synthesis; C—H bond activation; cascade reaction; 2-aryl-3H-indoles; cyclopropanols

Cite this article

Xueying Yang , Yuanshuang Xu , Xinying Zhang , Xuesen Fan . Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols[J]. Chinese Journal of Organic Chemistry, 2025 , 45(2) : 694 -706 . DOI: 10.6023/cjoc202406001

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