Pseudo-multicomponent 1,3-dipolar cycloaddition involving metal-free generation of unactivated azomethine ylides

Sansano, José M.; Belabbes, Asmaa; Foubelo, Francisco; Nájera, Carmén; Retamosa, Gracia; Sirvent, Ana; Yus, Miguel

doi:10.1039/d3ob00023k

Cited by 3 publications

(3 citation statements)

References 20 publications

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“…5 With these background factors in mind and our continuing interest in the construction of nitrogen-containing heterocycles, 6 herein, we present an atom-economic route, by which a large variety of fused-ring pyrrolizine derivatives were prepared via the reaction of N-substituted pyrrole-2-carboxaldehydes with Nsubstituted maleimides in the presence of DTBP in one pot under mild reaction conditions. It is worth noting that this programme achieves the activation of C(sp 3 )-H bonds under copper catalysis and constructs new C(sp 3 )-C(sp 2 )/C(sp 3 )-C(sp 3 ) bonds through a single electron transfer pathway (Scheme 1e).…”

Section: Synlettmentioning

confidence: 99%

“…1 As a typical example of pyrrolizines, tricyclic pyrrolizine frameworks have shown great potential for various applications in drug discovery. They serve as an important structural element for thrombin inhibitors 2 and drugs used in the treatment of cystic fibrosis (CF), 3 as depicted in Figure 1 . Therefore, it is an important task to develop integrated strategies for the simple, efficient, and convenient construction of complex and diverse fused-ring pyrrolizine derivatives from readily available scaffolds.…”

Section: Table 1 Reaction Optimization Amentioning

confidence: 99%

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Synthesis of Fused-Ring Pyrrolizine Derivatives via a Copper-Catalyzed Radical Cascade Cyclization

Ding,

Ji,

et al. 2024

Synlett

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Herein, an atom-economic method for the synthesis of fused-ring pyrrolizine derivatives by a cycloaddition reaction of easily accessible N-substituted pyrrole-2-carboxaldehydes with N-substituted maleimides in the presence of di-tert-butyl peroxide has been successfully developed. A total of 23 compounds were obtained by using this method, with a maximum yield of 72%, providing a practical and efficient method for the synthesis of tricyclic pyrrolizine frameworks.

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Section: Synlettmentioning

confidence: 99%

Section: Table 1 Reaction Optimization Amentioning

confidence: 99%

Synthesis of Fused-Ring Pyrrolizine Derivatives via a Copper-Catalyzed Radical Cascade Cyclization

Ding,

Ji,

et al. 2024

Synlett

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show abstract

“…In this sense, more sophisticated analogs 21 containing this polycycle 20 can be classified as promising drugs for this purpose. Some studies regarding herbicide and pesticide activities, as well as surveys for plant growth control, are under investigation (Belabbes et al, 2023). Notably, the 4-chlorophenyl group is present in the structures of three (22b-d) of these five active molecules.…”

Section: Polysubstituted Pyrrolidinesmentioning

confidence: 99%

Recent insights about pyrrolidine core skeletons in pharmacology

Poyraz,

Döndaş,

Döndaş

et al. 2023

Front. Pharmacol.

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To overcome numerous health disorders, heterocyclic structures of synthetic or natural origin are utilized, and notably, the emergence of various side effects of existing drugs used for treatment or the resistance of disease-causing microorganisms renders drugs ineffective. Therefore, the discovery of potential therapeutic agents that utilize different modes of action is of utmost significance to circumvent these constraints. Pyrrolidines, pyrrolidine-alkaloids, and pyrrolidine-based hybrid molecules are present in many natural products and pharmacologically important agents. Their key roles in pharmacotherapy make them a versatile scaffold for designing and developing novel biologically active compounds and drug candidates. This review aims to provide an overview of recent advancements (especially during 2015–2023) in the exploration of pyrrolidine derivatives, emphasizing their significance as fundamental components of the skeletal structure. In contrast to previous reviews that have predominantly focused on a singular biological activity associated with these molecules, this review consolidates findings from various investigations encompassing a wide range of important activities (antimicrobial, antiviral, anticancer, anti-inflammatory, anticonvulsant, cholinesterase inhibition, and carbonic anhydrase inhibition) exhibited by pyrrolidine derivatives. This study is also anticipated to serve as a valuable resource for drug research and development endeavors, offering significant insights and guidance.

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Dipolarophile‐Steered Formal Stereodivergent Synthesis of 2,5‐cis/trans‐Pyrrolidines Based on Asymmetric 1,3‐Dipolar Cycloaddition of Imino Lactones

Furuya,

Muroi,

Kanemoto

et al. 2023

Chemistry A European J

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The stereodivergent asymmetric synthesis of 2,5‐trans/cis pyrrolidines by 1,3‐dipolar cycloaddition using two different types of activated alkenes is described. When ylidene‐isoxazolones were employed as dipolarophiles, the Ag/(S,Sp)‐iPr‐FcPHOX‐catalyzed asymmetric [3+2] cycloaddition of imino lactones proceeded with 2,5‐trans selectivity. Subsequent decarboxylation of the isoxazolone rings produced pyrrolidines with 2,5‐trans stereoretention. In the reaction using acyclic enones as activated alkenes, the Ag/(R,Sp)‐ThioClickFerrophos complex‐catalyzed asymmetric [3+2] cycloaddition afforded 2,5‐cis substituted pyrrolidines in high yields and enantioselectivities. Therefore, these methods can be considered as a formal stereodivergent synthesis of 2,5‐cis/trans pyrrolidines.

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Pseudo-multicomponent 1,3-dipolar cycloaddition involving metal-free generation of unactivated azomethine ylides

Abstract: The pseudo-multicomponent reaction between propargyl amine, an aldehyde and an electron-deficient alkene is described. The C-H activation takes place thermally and allows to obtain cicloadducts in very good yields and...

Cited by 3 publications

References 20 publications

Synthesis of Fused-Ring Pyrrolizine Derivatives via a Copper-Catalyzed Radical Cascade Cyclization

Synthesis of Fused-Ring Pyrrolizine Derivatives via a Copper-Catalyzed Radical Cascade Cyclization

Recent insights about pyrrolidine core skeletons in pharmacology

Dipolarophile‐Steered Formal Stereodivergent Synthesis of 2,5‐cis/trans‐Pyrrolidines Based on Asymmetric 1,3‐Dipolar Cycloaddition of Imino Lactones

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