Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(4), P. 1364 - 1416

Published: Jan. 17, 2023

Hypervalent aryliodoumiums are intensively investigated as arylating agents. They excellent surrogates to aryl halides, and moreover they exhibit better reactivity, which allows the corresponding arylation reactions be performed under mild conditions. In past decades, acyclic aryliodoniums widely explored However, unmet need for is improvement of their notoriously low reaction economy because coproduced iodides during often wasted. Cyclic have intrinsic advantage in terms economy, started receive considerable attention due valuable synthetic applications initiate cascade reactions, can enable construction complex structures, including polycycles with potential pharmaceutical functional properties. Here, we summarizing recent advances made research field cyclic aryliodoniums, nascent design aryliodonium species applications. First, general preparation typical diphenyl iodoniums described, followed by heterocyclic monoaryl iodoniums. Then, initiated arylations coupled subsequent domino summarized construct polycycles. Meanwhile, building biaryls axial atropisomers discussed a systematic manner. Finally, very advance employed halogen-bonding organocatalysts described.

Language: Английский

---

Transition‐Metal‐Free Synthesis of Functionalized Quinolines by Direct Conversion of β‐O‐4 Model Compounds

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(38)

Published: July 23, 2022

Direct production of heterocyclic aromatic compounds from lignin β-O-4 models remains a huge challenge due to the incompatible catalysis for aryl ether bonds cleavage and ring formation. Herein, first example quinoline synthesis model by one-pot cascade reaction is reported in yields up 89 %. The pathway involves selective C-O bonds, dehydrogenation, aldol condensation, C-N bond formation along with construction. control experiments suggest that both imine chalcone were identified as key intermediates, rate determining step well preferred experimentally clarified supported density functional theory (DFT) calculations. Based on this protocol, conversion polymer delivered 56 wt % yield derivative three steps. This transformation provides potential petroleum-independent choice chemicals.

Language: Английский

---

Recent advances on biologically active coumarin-based hybrid compounds

Medicinal Chemistry Research, Journal Year: 2023, Volume and Issue: 32(4), P. 617 - 642

Published: Feb. 9, 2023

Language: Английский

---

Recent advances in functionalized quinoline scaffolds and hybrids—Exceptional pharmacophore in therapeutic medicine

Frontiers in Chemistry, Journal Year: 2023, Volume and Issue: 10

Published: Jan. 6, 2023

Quinoline is one of the most common nitrogen-containing heterocycles owing to its fascinating pharmacological properties and synthetic value in organic pharmaceutical chemistry. Functionalization this moiety at different positions has allowed for varying activities derivative. Several publications over last few decades have specified various methods synthesis. This includes classical synthesizing primary quinoline derivatives efficient that reduce reaction time with increased yield employing procedures fulfill twelve green chemistry principles, “safer solvent”. The metal nanoparticle-catalyzed also serves as a potent effective technique synthesis excellent atom efficiency. focus review highlight routes functionalized derivatives, including hybrids moieties predetermined bound which are interest drug candidates dual modes action, overcoming toxicity, resistance amongst others. was achieved using updated literature, stating biological mechanisms through these compounds administer relief. ADMET studies Structure-Activity Relationship (SAR) novel were highlighted explore drug-likeness quinoline-hybrids influence substituent characteristics position on activity compounds.

Language: Английский

---

Ring‐Opening Cross‐Coupling/Cyclization Reaction of Cyclopropanols with Organic Compounds

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(32)

Published: Aug. 23, 2023

Abstract Cyclopropanols, due to their particular chemistry, can participate in various synthetic reactions with retention or cleavage of the strained three‐membered ring. Direct cross‐coupling ring‐opening reaction such molecules access organic compounds, as ketones has great importance medicinal chemistry and material sciences. Hence, coupling reaction/cyclization cyclopropanols for constructing new valuable presence a transition metal catalyst under metal‐free conditions is described this context. The features are discussed, mechanisms challenging highlighted.

Language: Английский

---

Continuous Flow for the Photochemical Synthesis of 3-Substituted Quinolines

Organic Process Research & Development, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Language: Английский

---

Cobalt-Catalyzed Hypervalent Iodine(III) Promoted Cascade Annulation Reaction of Anilines with Formamides for 2-Aminobenzoxazoles Synthesis

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7571 - 7579

Published: May 17, 2023

Herein, we disclose a practical and simple procedure to synthesize 2-aminobenzoxaoles. Simple anilines formamides were used as substrates. The C–H bond ortho the amino group in was directly functionalized under cobalt-catalyzed conditions with high levels of functional tolerance. Hypervalent iodine(III) both an oxidant Lewis acid for this reaction. mechanism study showed that transformation may involve radical process.

Language: Английский

---

Evidence for Carbene Intermediates in Isocyanide Homologation by Aluminium(I)

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(34)

Published: June 15, 2023

The C-C bond formation between C1 molecules plays an important role in chemistry as manifested by the Fischer-Tropsch (FT) process. Serving models for FT process, we report here reactions a neutral AlI complex (Me NacNac)Al (1, Me NacNac=HC[(CMe)(NDipp)]2 , Dipp=2,6-diisopropylphenyl) and various isocyanides. step-by-step coupling mechanism was studied detail low-temperature NMR monitoring, isotopic labeling, well quantum chemical calculations. Three different products were isolated reaction of 1 with sterically encumbered 2,6-bis(benzhydryl)-4-Me-phenyl isocyanide (BhpNC). These substantiate carbene intermediates. adamantyl (AdNC) generated trimerization product, corresponding intermediate could be trapped form molybdenum(0) complex. Tri-, tetra-, even pentamerization less congested phenyl p-methoxyphenyl isocyanides (PhNC PMPNC) concurrent construction quinoline or indole heterocycles. Overall, this study provides evidence intermediates FT-type aluminium(I)

Language: Английский

---

Lewis Acid‐Promoted Domino Processes for the Synthesis of Homoallylic Amines, Quinolines and Tetrahydroquinolines

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 3010 - 3021

Published: May 1, 2024

Abstract Herein, the synthesis of homoallylic amines, quinolines, and tetrahydroquinolines has been demonstrated. The domino one‐pot multi‐component approach accomplished using Lewis acid‐catalyzed conditions. A useful scaffold construction strategy can be achieved by controlling electronic effect aniline rather than relying on reaction described method applies to a wide variety substrates embedded with diverse functional groups extended toward natural products. Suitable control experiments, real‐time NMR studies, DFT calculations have validated reported process. protocol outlines for synthesizing amines controlled properties anilines.

Language: Английский

---

Deaminative Cyclization of Tertiary Amines for the Synthesis of 2-Arylquinoline Derivatives with a Nonsubstituted Vinylene Fragment

Organic Letters, Journal Year: 2022, Volume and Issue: 25(1), P. 109 - 114

Published: Dec. 9, 2022

With triethylamine as a vinylene source, convenient protocol for the regioselective synthesis of β,γ-nonsubstituted 2-arylquinolines from aldehydes and arylamines has been accomplished. The deaminative cyclization is also extended to long-chain tertiary alkylamines, enabling diverse alkyl groups be concurrently installed into pyridine rings. This process demonstrates new conversion pathway simultaneous dual C(sp3)-H bond functionalization amines, wherein transient acyclic enamines generated in situ undergo Povarov reaction.

Language: Английский

---