Development of 1,2,3-triazole hybrids as multi-faced anticancer agents co-targeting EGFR/mTOR pathway and tubulin depolymerization

Bioorganic Chemistry, Journal Year: 2025, Volume and Issue: 156, P. 108153 - 108153

Published: Jan. 11, 2025

Language: Английский

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1,2-Redox Transpositions of Tertiary Amides

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(40), P. 21745 - 21751

Published: Sept. 27, 2023

Reactions capable of transposing the oxidation levels adjacent carbon atoms enable rapid and fundamental alteration a molecule's reactivity. Herein, we report 1,2-transposition atom level in cyclic acyclic tertiary amides, resulting one-pot synthesis 1,2- 1,3-oxygenated amines. This transfer was facilitated by careful orchestration an iridium-catalyzed reduction with functionalization transiently formed enamine intermediates. A novel 1,2-carbonyl transposition is described, breadth this redox strategy has been further explored development aminoalcohol enaminone syntheses. The diverse β-functionalized amine products were shown to be multifaceted valuable synthetic intermediates, accessing challenging biologically relevant motifs.

Language: Английский

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Lewis Acid‐Driven Inverse Hydride Shuttle Catalysis

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(27)

Published: March 29, 2024

Abstract Inverse hydride shuttle catalysis provides a multicomponent platform for the highly efficient synthesis of alkaloid frameworks with exquisite diastereoselectivity. However, number limitations hinder this method, primarily strict requirement electron‐deficient acceptors. Herein, we present general Lewis acid‐driven approach to address constraint, and have developed two broad strategies enabling modular complex azabicycles that were entirely unattainable using previous method. The enhanced synthetic flexibility facilitates streamlined asymmetric cyclization, leading concise total (−)‐tashiromine.

Language: Английский

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Synthesize of β-Amino Esters from Enamides via 1,8-Diazabicyclo[5.4.0]undecane-7-ene-Mediated Hydroalkylation

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 13, 2025

A 1,8-diazabicyclo[5.4.0]undecane-7-ene (DBU)-mediated hydroalkylation of enamides with malonic acid diesters/β-carbonyl esters has been established, featuring no metal involvement, mild reaction conditions, and good functional group tolerance. The protocol enables the expedited preparation a variety β-amino esters. Preliminary mechanistic investigations, encompassing control experiments capture key intermediates, have substantiated proposed DBU-mediated pathway.

Language: Английский

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The sulfenylation of enamine esters with heterocyclic thiols or disulfides in water and application to DNA-compatible chemistry

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111006 - 111006

Published: March 1, 2025

Language: Английский

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Microwave-assisted Synthesis of Heterocycles and their Anti-cancer Activities

Current Microwave Chemistry, Journal Year: 2023, Volume and Issue: 10(2), P. 135 - 154

Published: Sept. 1, 2023

Abstract: One of the most efficient non-conventional heating methods is microwave irradiation. In organic synthesis, irradiation has become a popular technique as it enhances product yields and purities, reduces reaction time from hours to minutes, decreases unwanted side reactions. Microwave-assisted synthesis utilizes dielectric volumetric an alternative activation method, which results in rapid more selective transformations because uniform heat distribution. Heterocyclic compounds have profound role drug discovery development process along with their applications agrochemicals, fungicides, herbicides, etc., making them prevalent form biologically relevant molecules. Hence, enormous efforts been made flourish green routes for high-yielding under sustainable tool. Among different clinical applications, heterocyclic received considerable attention anti-cancer agents. moieties always core parts drugs, including market-selling i.e., 5-fluoroura-cil, doxorubicin, methotrexate, daunorubicin, natural alkaloids, such vinblastine vincristine. this review, we focus on developments microwave-assisted heterocycles activities particular heterocycles.

Language: Английский

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A Neutral PC_NHCP Co(I)–Me Pincer Complex as a Catalyst for N-Allylic Isomerization with a Broad Substrate Scope

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4319 - 4325

Published: March 23, 2024

Earth-abundant-metal catalyzed double bond transposition offers a sustainable and atom-economical route toward the synthesis of internal alkenes. With an emphasis specifically on olefins ethers, isomerization allylic amines has been particularly under represented in literature. Herein, we report efficient methodology for selective N-allylic organic compounds, including amines, amides, imines. The reaction is by neutral PCNHCP cobalt(I) pincer complex proceeds via π-allyl mechanism. occurs readily at 80–90 °C, it compatible with wide variety functional groups. situ formed enamines could additionally be used one-pot inverse-electron-demand Diels–Alder to furnish series diversely substituted heterobiaryls, which further discussed this report.

Language: Английский

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A Neutral PCNHCP Co(I)-Me Pincer Complex as a Universal Catalyst for N-Allylic Isomerization

Published: Nov. 16, 2023

Earth-abundant metal catalyzed double bond transposition offers a sustainable and atom economical route towards the synthesis of internal alkenes. With emphasis specifically on olefins ethers, isomerization allylic amines has been particularly underrepresented in literature. Herein, we report an efficient methodology for selective N-allylic organic compounds including, amines, amides, imines. The reaction is by neutral PCNHCP Cobalt(I) pincer complex proceeds via π-allyl mechanism that includes unusual 1,2-methyl migration. occurs readily at 80 °C it compatible with wide variety functional groups. in-situ formed enamines, could additionally be used one-pot inverse-electron-demand Diels-Alder to furnish series diversely substituted hetero-biaryls, which further discussed this report.

Language: Английский

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Nickel-Catalyzed Alkene Isomerization to Access Bench-Stable Enamines and Their [3 + 2] Annulation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9233 - 9242

Published: June 24, 2024

Enamines are difficult to prepare on the bench due their instability, which results in side reactions, decompositions, poor yields, etc. Herein, we developed a simple and effective method for making bench-stable enamines using very low amount of nickel catalyst loading. The deuterium exchange, competitive reaction, radical clock experiment have all been found favor ionic mechanism this alkene isomerization. Scale-up [3 + 2] annulation reaction with activated cyclopropane deliver cyclopentane derivatives shown value organic synthesis.

Language: Английский

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Synthesis of 2,2-difunctionalized 2H-azirines via I₂-mediated annulation of enamines

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(11), P. 2292 - 2299

Published: Jan. 1, 2024

Various 2,2-difunctionalized 2 H -azirines were synthesized via I -mediated annulations of enamines in the presence nucleophiles under mild and transition metal-free conditions.

Language: Английский

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