Synthesis and crystal structure of piperidinyl propanenitrile towards the preparation of piperidine based bioactive films for drug delivery applications

Scientific Reports, Journal Year: 2025, Volume and Issue: 15(1)

Published: Jan. 3, 2025

Language: Английский

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Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2607 - 2612

Published: Jan. 1, 2024

A metal-free, scalable, and cascade protocol for assembling diverse polysubstituted pyridines from tertiary enaminones α,β-unsaturated sulfonylketimines by cleaving C–N/N–S bonds is reported.

Language: Английский

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Modular Construction of Chiral Aminopiperidine via Palladium-Catalyzed Hydroamination of 1,2-Dihydropyridine

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 12, 2025

In this study, we describe a generally straightforward methodology for the catalytic synthesis of chiral aminopiperidine from pyridine and azoles. The key step was palladium-catalyzed regioselective N–H insertion into double bond 1,2-dihydropyridine. This hydroamination exhibits wide substrate scope functional group compatibility. Mechanistic study revealed that C═C followed cis addition. utility protocol demonstrated by diverse functionalization enamine bond.

Language: Английский

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Unveiling Novel Synthetic Pathways through Brook Rearrangement

Synthesis, Journal Year: 2024, Volume and Issue: 56(16), P. 2483 - 2498

Published: Jan. 30, 2024

Abstract The Brook rearrangement is a valuable synthetic tool that facilitates the controlled construction of complex molecules. Conventionally, it generates carbanion intermediates utilized in subsequent functionalization reactions. In this review, we will explore recent advancements extend beyond traditional Specifically, highlight its involvement unusual bond cleavage, annulation reactions, and dearomatization efforts. novelty underscored by showcasing most applications. 1 Introduction 2 Novel Synthetic Pathways Involving Rearrangement 2.1 C–C C–X Bond Formation 2.2 Cleavage 2.3 Stereodefined Substituted Silyl Enol Allenol Ethers 2.4 Annulation Reactions 2.5 Dearomatization 3 Applications 4 Conclusion

Language: Английский

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Dearomative Spirocyclization of Ynamides

Chemical Science, Journal Year: 2024, Volume and Issue: 15(45), P. 19136 - 19141

Published: Jan. 1, 2024

Spiro N-heterocycles, particularly aza-spiro piperidines, have shown significant promise in pharmaceutical applications due to their ability enhance physicochemical properties. Despite potential, the preparation of these complex structures poses challenges. To address this, we propose a one-pot dearomative spirocyclization reaction ynamides. This method involves copper-catalyzed carbomagnesiation reaction, achieving chemo-, regio-, and stereoselective formation vinyl metal intermediates. Upon addition Lewis acid, intermediates undergo regioselective nucleophilic dearomatization event, facilitating synthesis diverse dihydropyridine scaffolds with multiple functional handles. Various Grignard reagents, ynamides, acylating reagents been explored. A subsequent hydrogenation provides access both partially fully reduced spirocyclic frameworks, broadening scope potential medicinal applications.

Language: Английский

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Regio‐, Site‐ and Stereo‐Selective Aziridination of Conjugated Dienes Enabled by Palladium/Copper/Iodide/Oxygen Cooperation

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Vinylaziridines are important building blocks in organic chemistry, especially the synthesis of nitrogen-containing heterocycles. The direct and efficient transfer an appropriate nitrogen source to readily accessible conjugated dienes is a notable methodology. Pd-catalyzed oxidative 1,2-difunctionalization through π-allyl-palladium species should be ideal method for selective vinylaziridines. However, this faces challenge regioselectivity, often resulting 1,4-difunctionalization instead. In study, we developed aerobic via achieve regio-, site- stereo-selective aziridination under synergistic effects Pd

Language: Английский

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Dearomative Transformation of Pyridin-3-ols into 2,3,6,7-Tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones via Oxidopyridinium/o-Quinodimethane (5 + 4) Cycloaddition

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

We report the dearomative transformation of pyridin-3-ols via oxidopyridinium (5 + 4) cycloaddition with o-quinodimethanes, leading to 2,3,6,7-tetrahydro-1H-2,6-methanobenzo[d]azonin-12-ones. The chemoselective derivatization obtained cycloadduct was also investigated demonstrate synthetic potential cycloadduct.

Language: Английский

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