Progress in Construction of 2H-Pyrrol-2-ones Skeleton

doi:10.6023/cjoc202207006

Abstract

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

Cite this article

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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Fig. & Tab. 17

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

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

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

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

Scheme 5. Reaction mechanism of propargylamine, halide and TFben

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

Scheme 7. Structure of the drug piracetam

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

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

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

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

Scheme 12. Mechanism of synthesis of pyrrolidone from imine intermediates

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]

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

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

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

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

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构建2H-吡咯-2-酮骨架的研究进展