构建2H-吡咯-2-酮骨架的研究进展

doi:10.6023/cjoc202207006

摘要/Abstract

2H-吡咯-2-酮作为一类重要的γ-内酰胺类化合物, 因其广泛存在于天然产物、药物和生物活性分子之中, 同时也是药物研发和有机合成中的主要合成中间体, 故备受有机合成工作者的关注. 近年来, 基于2H-吡咯-2-酮骨架包括1,5-二氢-2H-吡咯-2-酮的合成方法和策略取得了长足发展. 通过总结不同合成方法和策略, 分别对三类2H-吡咯-2-酮骨架的合成方法学的研究进展予以综述.

关键词: 2H-吡咯-2-酮, γ-内酰胺, 过渡金属催化, 串联环化反应

2H-Pyrrol-2-ones as an important class of γ-lactam compounds, widely exist in the structure of natural products, drugs and biologically active molecules, and they are also the important synthetic intermediates in drug development and organic synthesis. In recent years, the synthesis methods and strategies based on 2H-pyrrol-2-ones skeleton including 1,5-dihydro-2H-pyrrol-2-ones have made great progress. In this paper, the different synthetic methods and strategies for the construction of 2H-pyrrol-2-one skeletons are summarized.

Key words: 2H-pyrrol-2-one, γ-lactam, transition metal catalysis, cascade cyclization reaction

引用此文

刘东汉, 鲁席杭, 柴张梦洁, 杨浩琦, 孙瑜琳, 余富朝. 构建2H-吡咯-2-酮骨架的研究进展[J]. 有机化学, 2023, 43(1): 57-73.

Donghan Liu, Xihang Lu, Zhangmengjie Chai, Haoqi Yang, Yulin Sun, Fuchao Yu. Progress in Construction of 2H-Pyrrol-2-ones Skeleton[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 57-73.

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图/表 17

图1. 2H-吡咯-2-酮的分类

Figures 1. Classification of 2H-pyrrol-2-ones

图2. 一些重要的2H-吡咯-2-酮结构

Figures 2. Some important 2H-pyrrol-2-ones structures

图式3. 铜催化合成1,5-二氢-2H-吡咯-2-酮的机理

Scheme 3. Mechanism of copper-catalyzed synthesis of 1,5- dihydro-2H-pyrrol-2-one

图式4. 钯催化醛和胺反应的机理

Scheme 4. Mechanism of the reaction of aldehydes and amines catalyzed by palladium

图式5. 炔丙基胺、卤代物和TFben反应机理

Scheme 5. Reaction mechanism of propargylamine, halide and TFben

图式6. 镍催化乙酰胺与异氰化物反应的机理

Scheme 6. Mechanism of nickel-catalyzed reaction of acetamide with isocyanide

图式7. 吡拉西坦药物的结构

Scheme 7. Structure of the drug piracetam

图式8. 铑催化烯烃复分解合成2H-吡咯-2-酮

Scheme 8. Rhodium-catalyzed metathesis of olefins to synthesize 2H-pyrrol-2-ones

图式9. 2H-吡咯-2-酮合成恶唑霉素

Scheme 9. Synthesis of oxazomycin with 2H-pyrrol-2-ones as intermediate

图式10. 钴催化N-喹啉酰胺与三甲基(苯乙炔基)硅烷构建的代表性1,5-二氢-2H-吡咯-2-酮产物

Scheme 10. Co(II)-catalyzed annulation of benzamides with alkynylsilanes to construct the representative 1H-pyrrol-2(5H)- one derivatives

图式11. 靛红酮亚胺和3-溴丙烯醛反应的机理

Scheme 11. Mechanism of the reaction between isatin ketimine and 3-bromoacrolein

图式12. 亚胺中间体合成吡咯烷酮的机理

Scheme 12. Mechanism of synthesis of pyrrolidone from imine intermediates

图式13. 乙烯基碘化物合成2H-吡咯-2-酮机理

Scheme 13. Mechanism of synthesis of 2H-pyrrol-2-ones from vinyl iodide

Entry	R	X	Condition	Solvent	Yield	Time/h	Ref.
1	DABCO•(SO₂)₂or ArNH₂	OMe	blue LED, EY t-BuONO, 70 ℃, H₂O	CH₃CN	55%~91%	24	[62]
2	RSO₂Cl	OR, SMe, F, Cl, Br, I	blue LED, EY; Na₂CO₃, 100 ℃, H₂O	CH₃CN	68%~95%	20	[63]
3	RSO₄H or RSH	OMe	blue LED, Na₂EY, r.t. or blue LED, EY, r.t.	CH₃CN/H₂O (V/V=1/1)	37%~87%	24	[64]
4	RSeSeR	MeO, F, H	blue LED, EY, O₂, r.t.	CH₃CN	42%~92%	24	[65]
5	NH₄SCN	H	CFL LED, air, 35 ℃; Acr⁺-Mes^–ClO₄, AcOH	DCE	40%~95%	48	[66]
6	PIFA or KI	OMe	blue LED, NaOAc, r.t. or Xenon, NaOAc, r.t.	CH₃CN	52%~90%	2	[67]

表1. 光催化N-芳基丙烯酰胺自由基环化综述

Table 1. A review of photocatalytic radical cyclization of N-arylacrylamides

图式14. 光催化累积二烯烃合成1,5-二氢-2H-吡咯-2-酮反应机理

Scheme 14. Reaction mechanism of photocatalytic accumulation of diene to synthesize 1,5-dihydro-2H-pyrrol-2-one

图式15. 铑催化三氮唑合成1,3-二氢-2H-吡咯-2-酮的反应机理

Scheme 15. Reaction mechanism of rhodium-catalyzed synthesis of triazoles to 1,3-dihydro-2H-pyrrol-2-ones

图式16. 呋喃并3,4-二氢-2H-吡咯-2-酮的反应机理

Scheme 16. Reaction mechanism of furo-3,4-dihydro-2H-pyr- rol-2-one

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