Recent Progress in the Synthesis of 2-Benzofuran-1(3H)-one

doi:10.6023/cjoc202109006

Abstract

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

Cite this article

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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Fig. & Tab. 48

Scheme 1. Some biological activite compounds with isobenzofuranone skeleton

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

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

Scheme 4. Synthesis of 3-substituted isobenzofuranones

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

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

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

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

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

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

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

Scheme 12. Proposed mechanism for the synthesis of isobenzofuranones

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

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

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

Scheme 16. Oxidation of 2-enyl benzoic acid

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

Scheme 18. Selective synthesis of isocoumarins and isobenzofuranones

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

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

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

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

Scheme 23. Ruthenium-catalyzed oxidative alkenylations

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

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

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

Scheme 27. Synthesis of isobenzofuranones by visible-light catalysis

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

Scheme 29. Allylation of phthalaldehyde

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

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

Scheme 32. Proposed mechanism for synthesis γ-sulfonylated isobenzofuranones

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

Scheme 34. Coupling of alkynes and alcohols

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

Scheme 36. Possible reaction mechanism

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

Scheme 38. Reaction of cross-aldol/lactonization

Scheme 39. GB cyclization of bis-propargyl ethers

Scheme 40. One-pot synthesis of isobenzofuranones

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

Scheme 42. Method for the synthesis of polysubstituted isobenzofuranone derivatives

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

Scheme 44. Synthesis of isobenzofuranones

Scheme 45. The synthesis 3-substituted isobenzofuranones

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

Scheme 47. Proposed reaction pathway of cycloaddition reactions

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

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2-苯并呋喃-1(3H)-酮的合成研究进展