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Synthesis 2020; 52(04): 609-618
DOI: 10.1055/s-0039-1690746
DOI: 10.1055/s-0039-1690746
paper
Halogen-Radical-Promoted Dearomative Aza-Spirocyclization of Alkynylimines: An Efficient Approach to 3-Halo-Spirocyclohexadienones
This work was supported by the Natural Science Foundation of Shandong Province (No. ZR2018BB029, No. ZR2019PB004) and National Natural Science Foundation of China (21772067).Further Information
Publication History
Received: 21 September 2019
Accepted after revision: 31 October 2019
Publication Date:
13 November 2019 (online)
![](https://www.thieme-connect.de/media/synthesis/202004/lookinside/thumbnails/ss-2019-h0546-op_10-1055_s-0039-1690746-1.jpg)
Abstract
A novel halogen-radical-promoted dearomative aza-spirocyclization of alkynylimines for the synthesis of 3-halo-spirocyclohexadienones is described. In this process, it is believed that a radical addition, 5-exo-trig cyclization, and dearomative aza-spirocyclization are involved. Easily available starting materials, mild conditions, and a wide substrate scope make this approach potentially useful.
Key words
halogen radical - dearomative aza-spirocyclization - alkynylimine - 3-halo-spirocyclohexadienone - 5-exo-trig cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690746.
- Supporting Information
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For selected examples on Oxone chemistry, see:
For examples on alkynylimines, see:
For other dual-functionalized synthons, see: