Recent Progress on the Synthesis of Benzazepine Derivatives via Radical Cascade Cyclization Reactions

doi:10.6023/cjoc202209025

Abstract

Benzazepines are a kind of important seven-membered nitrogen-containing heterocyclic compounds, which are extensively exisited in natural products and pharmaceuticals, and have versatile biological activity. Therefore, great attention has been focused on the green and efficient synthesis of the benzazepines. In recent years, radical cascade cyclization reactions have gradually been developed as a powerful tool for the construction of benzazepines owing to their unique advantages. In this minireview, according to the different driving force of reaction, the research progress on the synthesis of benzazepines by radical cascade cyclization reactions in the past five years is systematically summarized in terms of photochemical reactions, electrochemical reactions and thermochemical reactions.

Key words: benzazepine derivatives, radical reaction, cascade cyclization reaction, visible-light photoredox catalysis

Cite this article

Qian Xiao, Qing-Xiao Tong, Jian-Ji Zhong. Recent Progress on the Synthesis of Benzazepine Derivatives via Radical Cascade Cyclization Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 3979-3994.

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Fig. & Tab. 20

Figure 1. Representative drugs molecules containing benzazepines unit

Scheme 1. Photocatalytic decarboxylative alkyl radical cascade for the synthesis of benzazepine derivatives

Scheme 2. Photoinduced synthesis of fluorinated dibenzazepine derivatives via radical cascade cyclization

Scheme 3. Visible-light-induced construction of difluoro-containing dibenzazepine derivatives via radical cascade cyclization

Scheme 4. Visible-light-induced radical cascade cyclization for the construction of alkyl-substituted dibenzazepine derivatives

Scheme 5. Visible-light-induced radical cascade cyclization to the synthesis of sulfone-containing dibenzazepine derivatives from sulfur dioxide

Scheme 6. Visible light-mediated radical cascade sulfonylation of alkynes for the synthesis of dibenzazepine derivatives

Scheme 7. Visible-light-induced radical cascade cyclization for the synthesis of sulfonated benzazepine derivatives

Scheme 8. Photocatalytic radical cascade cyclization for the synthesis of cyclohexyl benzazepine derivatives

Scheme 9. Visible-light-induced radical cascade cyclization to the synthesis of difluoromethyl dibenzazepine derivatives

Scheme 10. Photoinduced radical cascade cyclization for the synthesis of difluoroalkylated dioxodibenzothiazepine derivatives

Scheme 11. Photoinduced three-component cascade reaction for the construction of dioxodibenzothiazepine derivatives

Scheme 12. Photocatalytic radical cascade cyclization of alkynes with NH4SCN to synthesis dibenzazepine or dioxodibenzothiazepine derivatives

Scheme 13. Silver-catalyzed radical cascade cyclization of alkynes with acids to construct benzazepine derivatives

Scheme 14. Aldehyde auto-oxidation and decarbonylative radical cascade cyclization for the synthesis of benzazepine derivatives

Scheme 15. Metal-free decarboxylative radical cascade cyclization for the synthesis of benzazepine derivatives

Scheme 16. Copper-catalyzed trifluoromethylation/cascade cyclization of alkynes for the synthesis of dioxodibenzothiazepine derivatives

Scheme 17. Copper-assisted trifluoromethylthiolation/cascade cyclization of alkynes to synthesize dioxodibenzothiazepine derivatives

Scheme 18. Radical promoted trifluoromethylthiolation of alkynes for the synthesis of dibenzazepine or dioxodibenzothiazepine derivatives

Scheme 19. Synthesis of difluoromethyl dibenzazepine derivatives via electrochemical radical cascade cyclization reaction

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