Research Progress in Radical Cascade Reaction Using Nitrogen Heterocycle in Indoles as Radical Acceptors

doi:10.6023/cjoc202107012

Abstract

Indole skeleton has been widely utilized in the synthesis and late-stage modification of biologically active compounds, especially in the fields of medicines and pesticides. In recent years, constructing spiro compounds by asymmetric dearomatization of indoles has become extremely promising. Meanwhile, the radical tandem reaction of unsaturated bonds has been a significant branch of organic chemistry, and this methodology has become a crucial approach to modify the indole skeleton. Therefore, the recent progress in the field of radical cascade reaction of unsaturated hydrocarbon using nitrogen heterocycle in indoles as radical acceptors is summarized. Besides, the reaction design, mechanism and prospects of this field are also discussed.

Key words: indole, radical, cascade cyclization reactions, unsaturated bonds, difunctionalization

Cite this article

Wanwan Wang, Mingming Zhang, Wenchao Yang, Xiaohu Yang. Research Progress in Radical Cascade Reaction Using Nitrogen Heterocycle in Indoles as Radical Acceptors[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 75-84.

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Fig. & Tab. 20

Scheme 1. Functionalized indoles involved free radical reactions

Scheme 2. Isocyanides involved free radical reactions

Scheme 3. Radical cascade and dearomatization of indoles

Scheme 4. Radical cascade and dearomatization of indoles

Scheme 5. Radical cascade reaction of isocyanide

Scheme 6. Visible light-catalyzed cascade radical cyclization of N-propargylindoles with acyl chlorides

Scheme 7. Cascade cyclization of N-propargylindoles with α-keto acids

Scheme 8. Trifluoromethylation of ynones coupled with dearomatizing spirocyclization of indoles

Scheme 9. Phosphinoylation and cyclization of alkenes

Scheme 10. Phosphinoylation and cyclization of alkenes

Scheme 11. phosphinoylation and cyclization of alkynes

Scheme 12. Phosphinoylation and cyclization of alkynes

Scheme 13. Sulfonylation and cyclization of alkynes

Scheme 14. Sulfonylation and cyclization of N-propargylindoles

Scheme 15. Thioetherification and cyclization of alkynes

Scheme 16. Sulfonylation, cyclization and 1,2-aryl migration of N-propargylindoles

Scheme 17. Cascade thioetherification and cyclization of N-propargylindoles

Scheme 18. Thioetherification of ynones coupled with dearomatizing spirocyclization of indoles

Scheme 19. Selenoetherification of ynones coupled with dearomatizing spirocyclization of indoles

Scheme 20. Cascade cyclization of alkynes to access sulfonated indolo[1,2-a]-quinolones

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