2-苯并呋喃-1(3H)-酮的合成研究进展

doi:10.6023/cjoc202109006

摘要/Abstract

2-苯并呋喃-1(3H)-酮(异苯并呋喃酮)是合成多种环状化合物的前体, 许多天然产物中含有异苯并呋喃酮结构. 由于其广泛的生物活性, 及其在药学方面的广泛应用, 该类化合物的制备引起了极大关注. 将从过渡金属催化合成、酸碱催化合成以及其它合成方法等三方面总结了我们及其他课题组近十年在合成异苯并呋喃酮方面的工作.

关键词: 苯并异呋喃酮, 衍生物, 合成方法

2-Benzofuran-1(3H)-ones (isobenzofuranons) are multi-function precursors toward a variety of cyclic compounds as isobenzofuranon structure is ubiquitous in many natural products. Due to its extensive biological activity and wide application in medicinal chemistry, the preparation of these compounds has attracted great attention. In this paper, our and other research groups' work on the synthesis of isobenzofuranone in recent ten years from three aspects of transition metal catalytic synthesis, acid-base catalytic synthesis and other synthesis methods is summarized.

Key words: isobenzofuranone, derivative, synthetical method

引用此文

龚婷婷, 陈智斌, 刘妙昌, 成江. 2-苯并呋喃-1(3H)-酮的合成研究进展[J]. 有机化学, 2022, 42(4): 1085-1100.

Tingting Gong, Zhibin Chen, Miaochang Liu, Jiang Cheng. Recent Progress in the Synthesis of 2-Benzofuran-1(3H)-one[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1085-1100.

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图/表 48

图式1. 一些具有异苯并呋喃酮骨架的生物活性化合物

Scheme 1. Some biological activite compounds with isobenzofuranone skeleton

图式2. 铑催化邻苯二甲醛与芳基硼酸的反应

Scheme 2. Rh-catalyzed reaction of phthalaldehyde with arylboronic acids

图式3. Rh催化芳基硼酸和邻苯二甲醛合成异苯并呋喃酮可能的反应机理

Scheme 3. Proposed mechanism for the synthesis of isobenzofuranones from arylboric acid and phthalaldehyde

图式4. 3-取代异苯并呋喃酮的合成

Scheme 4. Synthesis of 3-substituted isobenzofuranones

图式5. 铑(III)催化合成异苯并呋喃酮化合物

Scheme 5. Rh(III)-catalyzed approaches to the synthesis of isobenzofuranones

图式6. 苯甲酸和脂肪酸或脂肪酸酐合成异苯并呋喃酮

Scheme 6. Synthesis of isobenzofuranones from benzoic acids and aliphatic acids or anhydrides

图式7. 铑催化苯甲酸与末端炔烃的氧化偶联反应

Scheme 7. Rhodium-catalyzed oxidative coupling of benzoic acids with terminal alkynes

图式8. 苯甲酸与末端炔烃合成异苯并呋喃酮可能的反应机理

Scheme 8. Proposed mechanism for the synthesis isobenzofuranones from benzoic acids with terminal alkynes

图式9. 铑(III)催化芳香酸和丙烯酸酯衍生物的反应

Scheme 9. Rh(III)-catalyzed reaction of aromatic acids and acrylate derivatives

图式10. 铑催化芳香酸和丙烯酸酯衍生物的反应

Scheme 10. Rh-catalyzed reaction of aromatic acids and acrylate derivatives

图式11. 钯催化邻苯二甲醛与芳基硼酸的反应

Scheme 11. Pd-catalyzed reaction of phthalaldehyde with arylboronic acids

图式12. 合成异苯并呋喃酮可能的反应机理

Scheme 12. Proposed mechanism for the synthesis of isobenzofuranones

图式13. 铑/钯催化邻苯二甲醛与有机三氟硼酸钾的反应

Scheme 13. Rh/Pd-catalyzed reaction of phthalaldehyde with potassium organotrifluoroborates

图式14. 钯催化合成3-(1'-吲哚)-异苯并呋喃酮的反应

Scheme 14. Palladium-catalyzed reactions for the synthesis of 3?(1'-indolyl)-isobenzofuranones

图式15. 形成3-(1'-吲哚基)-异苯并呋喃酮可能的反应机理

Scheme 15. Proposed reaction mechanism for the formation of 3-(1'-indolyl)-isobenzofuranones

图式16. 2-烯丙基苯甲酸的氧化反应

Scheme 16. Oxidation of 2-enyl benzoic acid

图式17. 铜-钯催化苯甲酸和苯丙酮环化合成异苯呋喃酮

Scheme 17. Copper-palladium-catalyzed annulation from benzoic acids and propiophenones for the synthesis of isobenzofuranones

图式18. 异香豆素和异苯并呋喃酮的选择性合成

Scheme 18. Selective synthesis of isocoumarins and isobenzofuranones

图式19. 钯催化苯甲酸和溴代炔烃的反应

Scheme 19. Palladium-catalyzed reaction of benzoic acid with bromoalkyne

图式20. 苯甲酸和溴代炔烃合成异苯并呋喃酮可能的反应机理

Scheme 20. Possible mechanism of synthesis of isobenzofuranones from benzoic acid and bromo-alkynes

图式21. 钌(II)-催化合成异苯并呋喃酮

Scheme 21. Ruthenium(II)-catalyzed synthesis of isobenzofuranones

图式22. 钌催化邻苯二甲酸酐和丙烯酸酯衍生物的反应

Scheme 22. Ruthenium-catalyzed reaction of phthalic anhydrides and acrylate derivatives

图式23. 钌催化的氧化烯基化反应

Scheme 23. Ruthenium-catalyzed oxidative alkenylations

图式24. 钌催化的芳香羧酸与炔烃反应

Scheme 24. Ruthenium-catalyzed reaction of aromatic carboxylic acids with alkynes

图式25. 钌催化苯甲酸和烯烃酸的反应

Scheme 25. Ruthenium-catalyzed reaction of benzoic acid with alkenoic acids

图式26. 钌催化苯甲酸与烯烃酸酯的反应

Scheme 26. Ruthenium(II)-catalyzed reaction of benzoic acids with alkenoic acids

图式27. 可见光催化合成异苯并呋喃酮

Scheme 27. Synthesis of isobenzofuranones by visible-light catalysis

. 图示28 苯甲酸与烯烃的交叉脱氢偶联反应

Scheme 28. Cross-dehydrogenative coupling/annulation of arene carboxylic acids and alkenes

图式29. 邻苯二甲醛的烯丙基化

Scheme 29. Allylation of phthalaldehyde

图式30. 铱催化芳香酸和丙烯酸酯衍生物的反应

Scheme 30. Ir-catalyzed reaction of aromatic acids and acrylate derivatives

图式31. 铜催化的2-乙烯基苯甲酸与亚磺酸钠的反应

Scheme 31. Copper-catalyzed reaction of 2-vinylbenzoic acids with sodium sulfonates

图式32. 合成γ-磺酰化异苯并呋喃酮的反应机理

Scheme 32. Proposed mechanism for synthesis γ-sulfonylated isobenzofuranones

图式33. 钴催化[2+2+2]环加成合成异苯并呋喃酮

Scheme 33. Synthesis of isobenzofuranones by cobalt catalyzed [2+2+2] cycloaddition

图式34. 炔烃和醇的偶联

Scheme 34. Coupling of alkynes and alcohols

图式35. 铼催化苯甲酰胺与醛的C—H键活化反应

Scheme 35. Rhenium-catalyzed C—H bond activation of benzoamide with aldehydes

图式36. 可能的反应机理

Scheme 36. Possible reaction mechanism

图式37. 邻羧基苯甲醛与苯乙酮衍生物合成异苯呋喃酮

Scheme 37. Synthesis of isobenzofuranones from o-carboxybenzaldehyde and acetophenone derivatives

图式38. 交叉羟醛/内酯化反应

Scheme 38. Reaction of cross-aldol/lactonization

图式39. 双炔丙基醚的GB环化

Scheme 39. GB cyclization of bis-propargyl ethers

图式40. 一锅法合成异苯并呋喃酮

Scheme 40. One-pot synthesis of isobenzofuranones

图式41. 邻炔基苯甲醛分子内环化“一锅法”合成异苯并呋喃酮

Scheme 41. “One-pot” synthesis of isobenzofuranones via intramolecular cyclization from ortho-alkynylbenzaldehydes

图式42. 多取代异苯并呋喃酮衍生物的合成方法

Scheme 42. Method for the synthesis of polysubstituted isobenzofuranone derivatives

图式43. 合成多取代异苯并呋喃酮衍生物可能的反应机理

Scheme 43. Possible mechanism for the synthesis of polysubstituted isobenzofuranone derivatives

图式44. 异苯并呋喃酮化合物的合成

Scheme 44. Synthesis of isobenzofuranones

图式45. 3-取代异苯并呋喃酮的合成

Scheme 45. The synthesis 3-substituted isobenzofuranones

图式46. 异氰酸酯的[4+1]环加成反应

Scheme 46. [4+1] Cycloaddition reactions of isocyanides

图式47. 环加成反应可能的反应途径

Scheme 47. Proposed reaction pathway of cycloaddition reactions

图式48. 硅甲基格氏试剂催化邻碘苯甲酸甲酯和酮合成异苯并呋喃酮

Scheme 48. Synthesis of isobenzofuranones from methyl ortho- iodobenzoates and ketones via using a silylmethyl Grignard reagent

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