基于自由基串联环化反应合成苯并吖庚因衍生物的研究进展

doi:10.6023/cjoc202209025

摘要/Abstract

苯并吖庚因骨架衍生物是一类重要的七元含氮杂环化合物, 广泛存在于天然产物和药物分子中, 具有多样的生物活性. 因此, 开发绿色、高效的苯并吖庚因骨架衍生物合成方法备受关注. 近年来, 自由基参与的串联环化反应凭借其独特的优势已逐渐发展成为构建该类骨架化合物的一种强有力工具. 根据不同的反应驱动力, 从光化学、电化学和热化学三方面系统地概括了近五年来通过自由基串联环化反应制备苯并吖庚因骨架衍生物的研究进展.

关键词: 苯并吖庚因衍生物, 自由基反应, 串联环化反应, 可见光氧化还原催化

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

引用此文

肖潜, 佟庆笑, 钟建基. 基于自由基串联环化反应合成苯并吖庚因衍生物的研究进展[J]. 有机化学, 2022, 42(12): 3979-3994.

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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图/表 20

图1. 含苯并吖庚因单元的代表性药物分子

Figure 1. Representative drugs molecules containing benzazepines unit

图式1. 光催化脱羧烷基自由基串联反应合成苯并吖庚因衍生物

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

图式2. 光诱导自由基串联环化反应合成氟化二苯并吖庚因衍生物

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

图式3. 可见光诱导的自由基串联环化反应构建二氟烷基取代的二苯并吖庚因衍生物

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

图式4. 可见光诱导的自由基串联环化反应构建烷基取代的二苯并吖庚因衍生物

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

图式5. 可见光诱导的自由基串联环化反应合成含磺酰基团的二苯并吖庚因衍生物

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

图式6. 可见光介导的炔烃自由基串联磺酰化反应合成二苯并吖庚因衍生物

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

图式7. 可见光诱导自由基串联环化反应合成磺酰基苯并吖庚因衍生物

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

图式8. 光催化自由基串联环化反应合成环己基苯并吖庚因衍生物

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

图式9. 可见光诱导自由基串联环化反应合成二氟甲基化二苯并吖庚因衍生物

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

图式10. 光诱导自由基串联环化反应合成二氟烷基二氧二苯并硫杂吖庚因衍生物

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

图式11. 光诱导三组分串联反应构建二氧二苯并硫杂吖庚因衍生物

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

图式12. 光催化炔烃与硫氰酸铵的自由基串联环化反应合成二苯并吖庚因或二氧二苯并硫杂吖庚因衍生物

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

图式13. 银催化炔烃与羧酸的自由基串联环化反应构建苯并吖庚因衍生物

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

图式14. 基于醛自氧化和脱羰基的自由基串联环化反应合成苯并吖庚因衍生物

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

图式15. 无金属参与的脱羧自由基串联环化反应合成苯并吖庚因衍生物

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

图式16. 铜催化炔烃的三氟甲基串联环化反应合成二氧二苯并硫杂吖庚因衍生物

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

图式17. 铜协助的炔烃三氟甲硫基串联环化反应合成二氧二苯并硫杂吖庚因衍生物

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

图式18. 自由基串联环化反应合成三氟甲硫基化二苯并吖庚因或二氧二苯并硫杂吖庚因衍生物

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

图式19. 基于电化学的自由基串联环化反应合成二氟甲基二苯并吖庚因衍生物

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

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