硫代黄烷酮类衍生物的合成研究进展

doi:10.6023/cjoc202301004

摘要/Abstract

硫代黄烷酮类化合物是黄酮类化合物的硫对应物, 在医药、材料科学和有机合成等领域有着广泛的应用. 因此, 发展高效的合成方法以获取结构多样的硫代黄烷酮类化合物具有重要的研究意义. 将按照硫代黄烷酮类化合物的分类, 对其合成方法和反应机理的关键步骤进行阐述, 并展望该研究领域的未来发展前景.

关键词: 硫代黄烷酮类化合物, 杂环化合物, 不对称合成, 过渡金属催化, 有机小分子催化

Thioflavonoids are the sulfur counterparts of flavonoids, which have a wide range of applications in the fields of medicine, material science, organic synthesis and others. Therefore, it is of great significance to develop efficient synthetic methods to obtain thioflavonoids with diverse structures. The synthetic approaches of thioflavonoids and key steps of reaction mechanisms according to the classification of thioflavonoids are summarized, and the development prospect of this research field is prospected.

Key words: thioflavonoids, heterocycles, asymmetric synthesis, transition-metal catalysis, organocatalysis

引用此文

蒙玲, 汪君. 硫代黄烷酮类衍生物的合成研究进展[J]. 有机化学, 2023, 43(3): 873-891.

Ling Meng, Jun Wang. Research Progress on Synthesis of Thioflavonoids[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 873-891.

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图/表 51

图1. 硫代黄烷酮类化合物的分类以及含有苯并噻喃结构的生物活性分子

Figure 1. Classification of thioflavonoids and bioactive molecules containing benzo thiopyran scaffold

图式1. (a)三氟甲磺酸催化连续的烷基化/环酰化反应; (b)可能的机理

Scheme 1. (a) Trifluoromethanesulfonic acid-catalyzed sequential alkylation/cyclic acylation reaction; (b) proposed mechanis

图式2. (a)铜催化2'-碘查尔酮或2'-溴查尔酮的串联反应; (b)可能的机理

Scheme 2. (a) Cu-catalyzed domino reaction of 2'-iodochalcones or 2'-bromochalcones; (b) proposed mechanism

图式3. 铑催化的炔烃氢酰化/硫共轭加成

Scheme 3. Rhodium-catalyzed alkyne hydroacylation/thio-conjugate addition

图式4. 二芳基铜酸盐与硫色酮的加成反应

Scheme 4. Addition reactions of thiochromones with diarylcuprates

图式5. (a)铜催化2'-碘/溴查尔酮与甲醛化次硫酸钠的串联反应; (b)可能的机理.

Scheme 5. (a) Cu-catalyzed domino reaction of 2'-iodo/bromochalcones and rongalite; (b) proposed mechanism

图式6. 2'-硝基查尔酮与黄原酸酯合成硫色满酮

Scheme 6. Synthesis of thiochromanones from 2'-nitrochalcones and xanthate

图式7. 铑催化芳基锌试剂与硫色酮的形式上共轭加成反应

Scheme 7. Rh-catalyzed formal conjugate addition of arylzinc reagents to thiochromones

图式8. 铜催化烷基溴化镁与硫色酮的形式上共轭加成反应

Scheme 8. Cu-catalyzed formal conjugate addition to thiochromones with alkylmagnesium bromides

图式9. Zn-ProPhenol催化丁烯内酯对(硫)色酮的插烯加成反应

Scheme 9. Zn-ProPhenol catalyzed vinylogous addition of butenolides to (thio)chromones

图式10. 铜催化硫色酮的对映选择性炔基化反应

Scheme 10. Cu-catalyzed enantioselective alkynylation of thiochromones

图式11. 铜催化硫色酮的炔基化反应的可能的反应机理

Scheme 11. Plausible mechanism of Cu-catalyzed alkynylation of thiochromones

图式12. 钌催化2-芳基(硫)色酮的不对称还原反应

Scheme 12. Ru-catalyzed asymmetric reduction of 2-aryl(thio)chromones

图式13. 铜催化(硫)色酮的不对称还原反应

Scheme 13. Cu-catalyzed asymmetric reduction of (thio)chromones

图式14. 分子内对映选择性催化Stetter反应

Scheme 14. Enantioselective catalytic intramolecular Stetter reaction

图式15. α-重氮酯与酮的亲电加成反应

Scheme 15. Electrophilic addition of α-diazoesters with ketones

图式16. 有机催化对映选择性质子化合成四氢萘酮、色满酮和硫色满酮

Scheme 16. Enantioselective synthesis of tetralones, chromanones, and thiochromanones by organocatalytic enantioselective protonation

图式17. 手性螺旋磷酸催化的Friedel-Crafts共轭加成/对映选择性质子化反应

Scheme 17. Chiral spiro phosphoric acid-catalyzed Friedel-Crafts conjugate addition/enantioselective protonation reactions

图式18. 钯催化环化反应合成硫色烯

Scheme 18. Pd-catalyzed cyclization for synthesis of thiochromenes

图式19. 铜催化串联法合成硫色烯

Scheme 19. Cu-catalyzed domino synthesis of thiochromenes

图式20. 邻溴苯甲醛和β-硝基苯乙烯与巯基磺酸钠的偶联反应

Scheme 20. Coupling reaction of o-bromobenzaldehydes and β-nitrostyrenes with sodium sulfidenonahydrate

图式21. 丙炔基硫醚加氢芳基化合成硫色烯衍生物

Scheme 21. Synthesis of thiochromene derivatives through hydroarylation of propargyl thioethers

图式22. 有机催化的对映选择性硫-迈克尔-羟醛串联反应

Scheme 22. Organocatalyzed tandem enantioselective thio- Michael-aldol reactions

图式23. 催化剂24促进α,β-不饱和醛和2-巯基苯甲醛的串联反应

Scheme 23. Catalyst 24-promoted cascade Michael-aldol reactions of α,β-unsaturated aldehydes with 2-mercaptobenzaldehydes

图式24. 有机催化2-巯基苯甲醛与α,β-不饱和噁唑烷酮的迈克尔-羟醛反应

Scheme 24. Organocatalyzed Michael-aldol reaction of 2-mercaptobenzaldehydes with α,β-unsaturated oxazolidinones

图式 25. 催化剂25促进的2-巯基苯甲醛与马来酰亚胺的串联迈克尔-羟醛反应

Scheme 25. Catalyst 25 promoted domino Michael-aldol reactions of 2-mercaptobenzaldehydes with maleimides

图式26. 催化剂24促进的2-巯基苯甲醛与烯醛的串联迈克尔-羟醛反应

Scheme 26. Catalyst 24 promoted domino thia-Michael/aldol reaction of 2-mercaptoacetophenones and enals

图式27. 2-巯基苯甲醛与β-硝基苯乙烯的对映选择性串联Michael-Henry反应

Scheme 27. Enantioselective tandem Michael-Henry reaction of 2-mercaptobenzaldehydes with β-nitrostyrenes

图式28. 2-巯基苯甲醛与α,β-不饱和酰胺的不对称硫-迈克尔-羟醛串联反应

Scheme 28. Asymmetric cascade sulfa-Michael-aldol reaction of 2-mercaptobenzaldehydes with α,β-unsaturated amides

图式29. (a)催化的迈克尔/霍纳-沃兹沃思-埃蒙斯串联反应; (b)对照实验

Scheme 29. (a) Catalytic Michael/Horner-Wadsworth-Emmons cascade reaction; (b) control reactions

图式30. 镍催化2-巯基苯甲醛与β-硝基苯乙烯的Michael-Henry反应

Scheme 30. Nickel-catalyzed Michael-Henry reaction of 2-mercaptobenzaldehydes with β-nitrostyrenes

图式31. 方酰胺催化的2-巯基苯甲醛与酮的不对称硫-迈克尔-羟醛串联反应

Scheme 31. Squaramide-catalyzed asymmetric sulfa-Michael/aldol cascade reaction of 2-mercaptobenzaldehydes and ketones

图式32. 方酰胺催化的2-巯基苯甲醛与β-吲哚基-β-三氟甲基烯酮的不对称硫-迈克尔-羟醛串联反应

Scheme 32. Squaramide catalyzed Michael-aldol reaction of 2-mercaptobenzaldehyde with β-indole-β-CF3 enones

图式33. 通过酰基转移不对称催化合成硫色烯的串联反应

Scheme 33. Asymmetric catalytic synthesis of thiochromenes via an acyl transfer-initiated cascade reaction

图式34. 镍催化亚甲基吲哚啉酮与硫代水杨醛的不对称迈克尔-羟醛反应

Scheme 34. Ni-catalyzed asymmetric Michael-Aldol reaction of methyleneindolinones and thiosalicylaldehydes

图式35. 镍催化亚甲基吲哚啉酮与硫代水杨醛的迈克尔-羟醛反应的可能的反应机理

Scheme 35. Plausible mechanism of Ni-catalyzed Michael- Aldol reaction of methyleneindolinones and thiosalicylaldehydes

图式36. I-Bidine催化的2-巯基苯甲醛与β-硝基苯乙烯的不对称迈克尔-羟醛反应

Scheme 36. I-Bidine catalyzed asymmetric Michael-aldol reaction of 2-mercaptobenzaldehydes with β-nitrostyrenes

图式 37. 催化的sulfa-Michael/Julia-Kocienski串联反应

Scheme 37. Catalytic cascade sulfa-Michael/Julia-Kocienski reaction

图式 38. 对映选择性的方酰胺催化的三氟甲基硫化反应-硫-迈克尔-羟醛串联反应

Scheme 38. Enantioselective squaramide-catalyzed trifluoromethylthiolation-sulfur-Michael/Aldol cascade reaction

图式39. 2-巯基苯甲醛与α,β-不饱和7-氮唑啉酰胺的对映选择性迈克尔-羟醛串联反应

Scheme 39. Enantioselective Michael-Aldol cascade reaction of 2-mercaptobenzaldehyde and α,β-unsaturated 7-azaindoline amides

图式40. 氨基环丙烷与硫酚的形式上[3+3]环化反应

Scheme 40. Formal [3+3] annulation reaction of aminocyclopropanes and thiophenols

图式41. 光诱导电子转移法合成硫色满衍生物的串联反应

Scheme 41. Domino synthesis of thiochromane derivatives via photoinduced electron transfer

图式42. 1,3-二烯的氢硫代反应/傅-克反应

Scheme 42. Hydrothiolation/Friedel-Crafts reaction of 1,3-dienes

图式43. [2-(苄基磺酰基)-苄基]咪唑酮的环化反应

Scheme 43. Cyclization of [2-(benzylsulfanyl)benzylidene]imi- dazolones

图式44. 钌催化含(E)-烯烃部分的丙炔醇分子内环化

Scheme 44. Ru-catalyzed intramolecular cyclization of propargylic alcohols bearing an (E)-alkene moiety

图式45. 苯胺与硝基烯烃烯酸酯的不对称Aza-Michael-Michael加成反应

Scheme 45. Asymmetric Aza-Michael-Michael addition of anilines to nitroolefin enoates

图式46. 氮杂卡宾催化的硫-迈克尔/迈克尔/内酯串联反应

Scheme 46. NHC-catalyzed sulfa-Michael/Michael/lactonization cascade reaction

图式47. 硫酯的串联转化合成硫色满

Scheme 47. Tandem transformation of thioesters for synthesis of thiochromanes

图式48. 方酰胺催化的硫-迈克尔/羟醛/内酯化串联反应

Scheme 48. Squaramide-catalyzed Sulfa-Michael/aldol/lactonization cascade reaction

图式49. 铜催化氨茴内酐的氢胺化反应

Scheme 49. Cu-catalyzed hydroamination with anthranils

图式50. 金催化邻炔基苯乙烯的双环化合成硫色满及其硒类似物

Scheme 50. Gold-catalyzed double-cyclization of o-(alkynyl)- styrenes for synthesis of thiochromanes and seleno analogues

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