Palladium-Catalyzed Cascade Carbonylation Reaction: Synthesis of Fused Isoindolinones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5625 - 5629

Published: July 2, 2024

A palladium-catalyzed cascade carbonylation reaction of 2-bromo-

Language: Английский

---

Using Quinolin-4-Ones as Convenient Common Precursors for a Metal-Free Total Synthesis of Both Dubamine and Graveoline Alkaloids and Diverse Structural Analogues

Molecules, Journal Year: 2024, Volume and Issue: 29(9), P. 1959 - 1959

Published: April 25, 2024

The Rutaceae family is one of the most studied plant families due to large number alkaloids isolated from them with outstanding biological properties, among quinoline-based Graveoline 1 and Dubamine 2. common methods for synthesis 2 their derivatives involves cycloaddition reactions or metal-catalyzed coupling processes but some limitations in scope functionalization quinoline moiety. As a continuation our current studies on chemical transformation 2-aminochalcones, we are reporting here an efficient metal-free approach total along analogues structural diversity, through two-step sequence involving intramolecular cyclization, oxidation/aromatization, N-methylation oxidative C-C bond processes, starting dihydroquinolin-4-ones as precursors construction structures both classes alkaloids.

Language: Английский

---

Oxidative [4+2] Annulation of Pyrrole‐2‐carbaldehyde Derivatives with o‐Hydroxyphenyl Propargylamines: Syntheses of 5,6,7‐Trisubstituted Indolizines

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(63)

Published: Aug. 23, 2024

Abstract A base promoted oxidative [4+2] annulation of pyrrole‐2‐carbaldehyde derivatives with o ‐hydroxyphenyl propargylamines for the synthesis highly substituted indolizines has been developed. Using DBN as base, a broad range 5,6,7‐trisubstituted have prepared in good to excellent yields under mild conditions, and many useful functional groups can be tolerated.

Language: Английский

---

Synthesis of Multisubstituted 2,3-Allenamides via Palladium-Catalyzed Carbonylation of Propargylic Esters

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 9001 - 9010

Published: June 6, 2024

2,3-Allenamides are an important class of unsaturated group-substituted carbonyl compounds. A palladium-catalyzed aminocarbonylation propargyl acetates with amines for the synthesized tri-/tetrasubstituted 2,3-allenamides has been developed. broad range have prepared from in good to excellent yields. The reaction featured mild conditions and functional group tolerance. applicability this methodology was further highlighted by late-stage modification several natural products pharmaceuticals.

Language: Английский

---

Lewis Acid Catalyzed [4 + 2] Annulation of Propargylic Alcohols with 2-Vinylanilines

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 16007 - 16017

Published: Oct. 31, 2023

An elegant Lewis acid catalyzed, protection-free, and straightforward synthetic strategy for the assembly of a series sophisticated polycyclic quinoline skeletons employing propargylic alcohols 2-vinylanilines as substrates in presence Yb(OTf)3 (10 mol %) AgOTf tetrahydrofuran has been described. This annulation protocol, which proceeds through sequential Meyer-Schuster rearrangement/nucleophilic substitution/deprotonation sequence, provides versatile, practical, atom-economical approach accessing derivatives moderate-to-good yields.

Language: Английский

---

Photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(3), P. 513 - 520

Published: Dec. 18, 2023

A photoredox radical cascade cyclization reaction for the effective construction of 2,4-disubstituted quinolines at room temperature is described. It shows good substrate suitability and functional group compatibility.

Language: Английский

---

Zinc‐Mediated Carbamoyl Amination of Alkylidenecyclopropane‐Tethered Carbamoyl Chlorides: Synthesis of Functionalized 2‐Quinolones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4644 - 4648

Published: Aug. 20, 2024

Abstract The transition metal catalyzed cyclization of alkene‐tethered carbamoyl chloride has emerged as a tool to construct oxindoles bearing quaternary centers. Most these reactions proceed via carbometalation‐initiated 5‐ exo ‐trig followed by nucleophilic trapping the resulting σ alkyl‐metal species achieve diverse functionalized oxindoles. 6‐ endo type been rarely reported. Herein, zinc‐mediated amination alkylidenecyclopropane‐tethered chlorides with anilines for synthesis 2‐quinolones was developed. A range different substituted were prepared in 65–89% yield from and aniline derivatives using Zn/TMSCl system.

Language: Английский

---