Recent advances in the application of ylide-like species in [4 + 1]-annulation reactions: an updated review

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(19), P. 5358 - 5382

Published: Jan. 1, 2022

In this review, the advances made over last 6 years in [4 + 1]-annulation reactions involving sulfonium, sulfoxonium and ammonium ylides, as well diazo compounds carbenes are summarized.

Language: Английский

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Development of novel transition metal-catalyzed synthetic approaches for the synthesis of a dihydrobenzofuran nucleus: a review

RSC Advances, Journal Year: 2024, Volume and Issue: 14(21), P. 14539 - 14581

Published: Jan. 1, 2024

The synthesis of dihydrobenzofuran scaffolds bears pivotal significance in the field medicinal chemistry and organic synthesis. These heterocyclic hold immense prospects owing to their significant pharmaceutical applications as they are extensively employed essential precursors for constructing complex frameworks. Their versatility importance make them an interesting subject study researchers scientific community. While exploring synthesis, have unveiled various novel efficient pathways assembling core. In wake extensive data being continuously reported each year, we outlined recent updates (post 2020) on methodological accomplishments employing catalytic role several transition metals forge functionalities.

Language: Английский

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Catalytic Enantioselective [4+1]-Annulation of Carboxylic Acids with Cyclopropenes

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

Published: Feb. 12, 2025

An efficient asymmetric synthesis of 3-vinylphthalides has been accomplished through rhodium-catalyzed [4+1]-annulation arylcarboxylic acids with cyclopropenes involving C–H bond functionalization. The method exhibited excellent compatibility for various functional groups and offered diverse substituted in yield enantioselectivity. Synthetic application control experiments were also performed to demonstrate the utility understand reaction pathway.

Language: Английский

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Cobalt-catalyzed multisubstituted allylation of the chelation-assisted C–H bond of (hetero)arenes with cyclopropenes

Chemical Science, Journal Year: 2021, Volume and Issue: 12(40), P. 13442 - 13449

Published: Jan. 1, 2021

Cp*Co III -catalyzed ring-opening isomerization of cyclopropenes to cobalt vinylcarbene has been utilized for the synthesis multisubstituted allylarenes via directing group-assisted functionalization C–H bonds arenes and heteroarenes.

Language: Английский

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Cooperative Rh(II)/Pd(0) Dual Catalysis: Synthesis of Highly Substituted 3(2H)-Furanones with a C2-Quaternary Center via a Cyclization/Allylic Alkylation Cascade of α-Diazo-δ-keto-esters

Organic Letters, Journal Year: 2021, Volume and Issue: 23(23), P. 9151 - 9156

Published: Nov. 15, 2021

A cooperative Rh(II)/Pd(0) dual-catalysis strategy that promotes a cyclization/allylic alkylation cascade of stable α-diazo-δ-keto-esters has been developed. Highly substituted 3(2H)-furanones with C2-quaternary center can be obtained efficiently under mild conditions via one-pot synthesis. Remarkably, this binary catalytic system shows high chemo-, regio-, and stereoselectivity excellent tolerance to various functionalities.

Language: Английский

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Catalytic Functionalization of Metallocarbenes Derived from α‐Diazocarbonyl Compounds and Their Precursors

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(12), P. 3872 - 3883

Published: Aug. 26, 2021

Abstract Short and efficient synthesis of heterocyclic compounds are highly desirable in synthetic organic chemistry. It is a dream approach to accomplish these syntheses from readily available starting materials single step. In this personal account, we discuss our contribution the beyond N‐sulfonyl‐1,2,3‐triazoles α‐diazocarbonyl compounds, which precursors for α‐imino (carbonyl) metal carbenes presence transition catalysts. Functionalization α‐imino(carbonyl) has been achieved through in‐situ generated metal‐stabilized ylides followed by either intramolecular trapping non‐polar bonds, rearrangement, cycloaddition, or 1,3‐insertion fashion, led various synthetically important intermediates compounds.

Language: Английский

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Identification of Non-steroidal Aromatase Inhibitors via In silico and In vitro Studies

Medicinal Chemistry, Journal Year: 2023, Volume and Issue: 19(10), P. 986 - 1001

Published: April 3, 2023

Breast cancer is the most common affecting women worldwide, including Pakistan. More than half of breast patients have hormone-dependent cancer, which developed due to over-production estrogen (the main hormone in cancer).The biosynthesis catalyzed by aromatase enzyme, thus serves as a target for treatment cancer. During current study, biochemical, computational, and STD-NMR methods were employed identify new inhibitors. A series phenyl-3- butene-2-one derivatives 1-9 synthesized evaluated human placental inhibitory activity. Among them, four compounds 2, 3, 4, 8 showed moderate weak activity (IC50 = 22.6 - 47.9 µM), compared standard drugs, letrozole 0.0147 ± 1.45 anastrozole 0.0094 0.91 exemestane 0.2 0.032 µM). Kinetic studies on two inhibitors, 4 8, revealed competitive- mixed-type inhibition, respectively.Docking all active indicated their binding adjacent heme group interaction with Met374, critical residue aromatase. further highlighted interactions these ligands enzyme.STD-NMR-based epitope mapping close proximity alkyl chain followed an aromatic ring receptor (aromatase). These also found be non-cytotoxic against fibroblast cells (BJ cells). Thus, study has identified inhibitors (compounds 8) pre-clinical clinical research.

Language: Английский

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Rhodium Catalyzed [4 + 1]-Annulation of o-Acylanilines with 3-Diazoindoline-2-imines

Organic Letters, Journal Year: 2023, Volume and Issue: 25(34), P. 6357 - 6362

Published: Aug. 21, 2023

An efficient rhodium catalyzed [4 + 1]-annulation of o-acylanilines with 3-diazoindoline-2-imines has been successfully accomplished for the synthesis spiroindolines in good to excellent yield. The reaction occurs through formation N-ylide followed by cyclization and showed tolerance various functional groups. Gram-scale synthesis, diastereoselective construction tetrasubstituted indoline, spirooxindole, isolation potential intermediates have also demonstrated.

Language: Английский

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Three-component chemo-selective oxy-allylation of α-diazo carbonyl compounds: Access to α-ternary carboxylic esters

Journal of Catalysis, Journal Year: 2022, Volume and Issue: 417, P. 52 - 59

Published: Nov. 26, 2022

Language: Английский

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Three-component acyloxylation of diazo compounds with carboxylic acids and azadienes

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(5), P. 925 - 929

Published: Dec. 28, 2022

Despite many studies on benzofuran-derived azadiene being reported, multi-component have scarcely been reported this heterocyclic skeleton. The first cascade three-component acyloxylation of diazos with acids and azadienes has under mild conditions. reaction is applicable to various (A/A) diazo compounds, generating diverse complex benzofuran derivatives.

Language: Английский

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