光/电化学驱动螺环化合物的合成研究进展

doi:10.6023/cjoc202304014

摘要/Abstract

螺环作为一种重要的有机分子骨架, 在有机化学、药物化学、材料科学等领域中广泛存在. 由于螺环骨架具有较大的三维空间结构, 满足药物设计中对构象刚性的需求, 因此开发高效的螺环化合物的合成方法尤为重要. 近年来, 光催化和电催化作为绿色、高效的合成手段, 为螺环化合物的合成注入了新的潜力. 主要按螺[4.5]类骨架、螺[5.5]类骨架、螺[2.3]类骨架以及螺吲哚类骨架的构建进行了分类, 并从光催化和电催化合成两个方面对螺环化合物的构建进行了综述.

关键词: 螺环, 光催化

As important organic molecular frameworks, spirocycles exist widely in organic chemistry, medicinal chemistry, material science and other fields. Since the spirocyclic skeleton has a large three-dimensional space structure, which meets the demand for conformational rigidity in drug design, it is particularly important to develop efficient synthetic methods for spirocyclic compounds. In recent years, photocatalysis and electrocatalysis have injected new potential into the synthesis of spirocyclic compounds as green and efficient synthetic methods. This article is mainly classified by the construction of snail [4.5] skeleton, snail [5.5] skeleton, snail [2.3] skeleton, and spiro-indoles skeleton. Moreover, the construction of spirocyclic compounds is reviewed from two aspects: photocatalysis and electrocatalytic synthesis.

Key words: spirocycles, photocatalysis

引用此文

陈宁, 张成栋, 李鹏, 仇格, 刘颖杰, 张天雷. 光/电化学驱动螺环化合物的合成研究进展[J]. 有机化学, 2023, 43(7): 2293-2303.

Ning Chen, Chengdong Zhang, Peng Li, Ge Qiu, Yinjie Liu, Tianlei Zhang. Research Progress in Synthesis of Spirocyclic Compounds Driven by Photo/Electrochemistry[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2293-2303.

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图/表 26

图式1. 可见光诱导α-溴-N-苄基烷基胺构建2-氮杂螺[4.5]癸烷

Scheme 1. Visible-light-induced construction of 2-azaspiro- [4.5]decane from α-bromo-N-benzylalkylamine

图式2. 光氧化还原含酮肟结构的苯酚衍生物构建螺吡咯啉

Scheme 2. Construction of spiropyrrolines by photoredox of phenol derivatives containing ketoxime structure

图式3. 可见光诱导联芳基化合物构建螺环内酯

Scheme 3. Visible-light-induced construction of spirolides from biaryl compounds

图式4. 光氧化还原卤代芳烃构建螺环己二烯化合物

Scheme 4. Construction of spironocyclohexadiene compounds by photoredox of halogenated aromatic hydrocarbons

图式5. 光氧化还原芳香族羧酸构建螺环化合物

Scheme 5. Construction of spiral ring compounds by photoredox aromatic carboxylic acids

图式6. 光催化N-苄基丙酰胺构建氮杂螺[4.5]十-6,9-二烯- 3,8-二酮

Scheme 6. Photocatalytic construction of azaspiro[4.5]deca-6,9- diene-3,8-dione from N-benzylpropionamide

图式7. 可见光诱导烯烃构建3-磺酰氮杂螺[4.5]三烯酮

Scheme 7. Visible-light-induced construction of 3-sulfonyl- azaspiro[4.5]trienone from alkenes

图式8. 可见光诱导2-溴-1,3-二羰基化合物构建碳螺环化合物

Scheme 8. Visible-light-induced construction of carbospirocyclic compounds from 2-bromo-1,3-dicarbonyl compounds

图式9. 可见光诱导丙酰胺、苯胺和二氧化硫合成磺化螺[4.5]三烯酮

Scheme 9. Visible-light-induced synthesis of sulfonated spiro[4.5]trienone from propionamide, aniline and sulfur dioxide

图式10. 可见光诱导丙烯酰胺和噻吩化合物构建3-硫氮螺[4.5]三烯酮

Scheme 10. Visible-light-induced construction of 3-thiazaspiro- [4.5]trienone from acrylamide and thiophene compounds

图式11. 可见光诱导N-芳基丙酰胺构建卤代螺[4.5]三烯酮

Scheme 11. Visible-light-induced construction of halospiro- [4.5]trienones from N-arylpropionamides

图式12. 可见光诱导N-芳基丙酰胺构建3-二氟甲基螺酮[4.5]三烯酮

Scheme 12. Visible-light-induced construction of 3-difluoro- methylspirone[4.5]trienone from N-arylpropionamides

图式13. 可见光诱导联芳基化合物构建螺[5.5]三烯酮

Scheme 13. Visible-light-induced construction of spiro[5.5]- trienone from biaryl compounds

图式14. 可见光诱导芳基炔酮构建螺[5.5]三烯酮

Scheme 14. Visible-light-induced construction of spiro[5.5]- trienone from aryl alkynone

图式15. 可见光诱导吲哚衍生物构建螺吲哚啉

Scheme 15. Visible-light-induced construction of spiroindolines from indole derivatives

图式16. 可见光诱导吲哚系炔酮构建螺环吲哚类化合物

Scheme 16. Visible-light-induced construction of spiro-indoles by indole-based alkynones

图式17. 可见光诱导亚甲基环丙烷构建多取代螺[2.3]环骨架

Scheme 17. Visible-light-induced construction of multi-substituted spiro[2.3] ring skeletons from methylenecyclopropane

图式18. 可见光诱导呋喃一锅转化为1-氮杂环生物碱骨架

Scheme 18. Visible-light-induced one-pot conversion of furan to 1-azacyclic alkaloid skeleton

图式19. 可见光诱导环化反应构建桥联螺环化合物

Scheme 19. Visible-light-induced construction of spiro-bridged compounds through cyclization

图式20. 可见光诱导N-烯丙基磺酰胺和烯烃构建β-螺旋环吡咯烷

Scheme 20. Visible-light-induced N-allylsulfonamide and construction β-helical cyclopyrrolidine from olefin

图式21. 电化学诱导芳基螺环化构建螺[4.5]三烯酮

Scheme 21. Electrochemically induced cyclization of aryl spirocyclization to construct spiro[4.5]trienone

图式22. 电催化卤化N-芳基烷基酰胺合成螺[4.5]三烯酮

Scheme 22. Electrocatalytic synthesis of spiro[4.5]trienone by halogenation of N-arylalkylamides

图式23. 电催化芳基衍生物合成3-卤代螺[4.5]三烯酮

Scheme 23. Electrocatalytic synthesis of 3-halogenated spiro[4.5]trienones from aryl derivatives

图式24. 电催化联芳基化合物合成二氟/三氟甲基化螺[5.5]三烯酮

Scheme 24. Electrocatalytic synthesis of sifluoro/trifluoro- methylated spiro[5.5]trienones from biaryl compounds

图式25. 电催化AgSCF3构建螺[5.5]三烯酮

Scheme 25. Electrocatalytic construction of spiro[5.5]trienone from AgSCF3

图式26. 电催化联芳基化合物合成硒化二苯环庚酮/螺[5.5]三烯酮

Scheme 26. Electrocatalytic synthesis of selenide diphenylcycloheptone/spiro[5.5]trienone from biaryl compounds

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