Theoretical Investigation of Cp*CO(III)-Mediated Regioselective [4 + 2]-Annulation of N-Chlorobenzamide with Vinyl Acetate for the Synthesis of Isoquinolone DOI Open Access
Nan Lu, Chengxia Miao, Xiaozheng Lan

et al.

Heterocycles, Journal Year: 2023, Volume and Issue: 106(8), P. 1385 - 1385

Published: Jan. 1, 2023

The mechanism is investigated for regioselective [4 + 2]-annulation of N-chlorobenzamide catalyzed by Cp*Co(III).The CoCp*(OAc)2-mediated ortho-cobaltation via acetate-aided N-H and C-H deprotonation furnishes a five-membered intermediate, which coordinative inserted into alkene giving seven-membered cobaltacycle.The reductive elimination oxidative addition CoCp*(I) species afford six-membered ring.The recovery CoCp*(III) assisted one AcOH vinyl acetate with OAc group available to cleavage as ligand.Two ligands are both supplied ketone COMe difficult break.The acetate-assisted tautomerization produces isoquinolin-1(2H)-one.The 3-acetylisoquinolin-1(2H)-one given dehydrooxidation.The promotion Cp*Co(III) lies in the barrier decrease most steps especially deprotonation.AcOH functions protonation Cl, N sources CoCp*(III).These results supported Multiwfn analysis on FMO specific TSs MBO value vital bonding, breaking.As common heterocyclic skeletons, isoquinolones present various natural products pharmaceuticals.Their derivatives exhibit broad medicinal properties, including antitumor, antiobesity, antiviral, other effects. 1,2Hence, development practical efficient synthetic protocol construction their analogues continuous need chemists.4][5] In recent years, some novel protocols have constantly emerged such Rh(III)-catalyzed 1385

Language: Английский

Synthesis of CF3–Isoquinolinones and Imidazole-Fused CF3–Isoquinolinones Based on C–H Activation-Initiated Cascade Reactions of 2-Aryloxazolines DOI

Miaomiao Liang,

Shengnan Yan,

Yuanshuang Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10180 - 10196

Published: July 4, 2024

Presented herein are novel syntheses of CF

Language: Английский

Citations

9
Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones DOI

Alexander Yu. Belyy,

Alena D. Sokolova,

Rinat F. Salikov

et al.

Mendeleev Communications, Journal Year: 2025, Volume and Issue: 35(2), P. 162 - 164

Published: Jan. 1, 2025

Language: Английский

Citations

1
Masters of Mediation: MN(SiMe3)2 in Functionalization of C(sp3)−H Latent Nucleophiles DOI
Ramdas Sreedharan, Thirumanavelan Gandhi

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(29)

Published: March 18, 2024

Abstract Organoalkali compounds have undergone a far‐reaching transformation being coupling partner to mediator in unusual organic conversions which finds its spot the field of sustainable synthesis. Transition‐metal catalysis has always been priority C( sp 3 )−H bond functionalization, however alternatively, recent times this seriously challenged by earth‐abundant alkali metals and their complexes arriving at new organometallic reagents. In line, importance MN(SiMe ) 2 (M=Li, Na, K & Cs) reagent revived functionalization over years synthesis is showcased minireview. with higher reactivity, enhanced stability, bespoke cation‐π interaction shown eye‐opening mediated processes such as )−C( cross‐coupling, radical‐radical aminobenzylation, annulation, aroylation, other transformations utilize readily available petrochemical feedstocks. This article also emphasizes reactivity unreactive robust C−X (X=O, N, F, C) cleavage reactions that occurred alongside functionalization. Overall, review encourages community exploit untapped potential inspires them take up subject even greater heights.

Language: Английский

Citations

6
Alkaline-Metal-Promoted Divergent Synthesis of 1-Aminoisoquinolines and Isoquinolines DOI
Peng Ma, Yuhang Wang, Ning Ma

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 1235 - 1240

Published: Jan. 9, 2024

Alkaline-metal-promoted divergent syntheses of 1-aminoisoquinolines and isoquinolines have been reported involving 2-methylaryl aldehydes, nitriles, LiN(SiMe3)2 as reactants. In addition, the three-component reaction has developed to furnish 1-aminoisoquinolines. This protocol features readily available starting materials, excellent chemoselectivity, broad substrate scope, satisfactory yields.

Language: Английский

Citations

4
Recent Advancement in the Conversion of 1,2,3‐Benzotriazin‐4(3H)‐One to Other Heterocyclic Systems and Their Applications: A Concise Review DOI Open Access
Zunera Khalid, Hafiz Adnan Ahmad, Munawar Ali Munawar

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(5)

Published: Feb. 1, 2025

Abstract The nitrogen containing 1,2,3‐benzotriazin‐4(3 H )‐one is structurally worthwhile system for its notable applications in the synthesis of N─ , O ─ and S─ heterocycles bears pivotal significant usage pharmaceutical industrial chemicals. Today most common items like dyes, cosmetics, sanitizers, insecticides plastics are based on heterocyclic moieties. Different starting materials used industrially formation diverse but a valuable structure to prepare numerous products. These conversions radiation or metal‐catalyzed denitrogenation annulation type reactions provide easy, one‐step atom‐economical route. vast significance their cheap make this subject interesting scientific researchers industrialists. This mini review summarizes recent developments transformation ring various other structures phenanthridinones, isoquinolones, coumarin‐1‐imines, benzamides, pyrroloquinazolinones, indolin‐1‐ones, 1,2‐benzisoselenazol‐3(2 )‐ones benzofuranones. Some emerging drugs ebselen, losartan, irbesartan, luotonin A, deoxyvasicinone mackinazolinone have been successfully synthesized from differently substituted benzotriazinones.

Language: Английский

Citations

0
Base-Promoted Annulation of o-(Cyanomethyl)aryl Thioester with Thiophenols to Access 3-Thiolated Isoquinolones DOI

Yuanyuan Fu,

Hui Liang,

F. Li

et al.

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

Published: Feb. 5, 2025

An efficient annulation approach to forming 3-thiolated isoquinolones from readily accessible o-(cyanomethyl)aryl thioesters and thiophenols has been established. This metal-free is achieved by taking advantage of solvent-free reactions with no precaution exclude water or air, enabling broad substrate scope good functionality tolerance. Furthermore, the protocol scalable offers facile access valuable without chromatography.

Language: Английский

Citations

0
Photoredox-Enabled Deconstructive [5 + 1] Annulation Approach to Isoquinolones from Indanones in Water DOI

Yuanyuan Fu,

Hui Liang,

Yanju Lu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3043 - 3047

Published: April 5, 2024

We disclose a deconstructive [5 + 1] annulation protocol for the synthesis of isoquinolones through nitrogen insertion into abundant indanones. This method exploits photoredox-catalyzed ring-opening oxime esters. The reaction proceeds smoothly with water as medium and tolerates range functional groups on diverse thiophenols, amines, or Moreover, representative exhibit promising antifungal activities.

Language: Английский

Citations

3
Copper-Catalyzed Three-Component Tandem Cyclization for One-Pot Synthesis of Indole-Benzofuran Bis-Heterocycles DOI
Peng Ma, Yuhang Wang, Jianhui Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 22, 2024

A one-pot, three-component synthesis of indole-benzofuran bis-heterocycles from terminal alkynes, salicylaldehydes, and indoles has been developed via copper-catalyzed tandem annulation. This catalytic system utilizes readily available starting materials, enabling predictable with broad substrate versatility, excellent regiocontrol, gram-scale amenability. The reaction proceeds a sequential pathway involving A3 coupling, 1,4-conjugate addition, 5-exo-dig cyclization.

Language: Английский

Citations

2
Ru- and Co-Catalyzed Intermolecular Carbonyl–Alkyne Metathesis Reactions of 1H-Indene-1,2,3-triones with Internal Alkynes DOI
Yuhang Wang, Peng Ma, Jianhui Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3164 - 3168

Published: March 29, 2024

The catalyst-dependent intermolecular carbonyl–alkyne metathesis (CAM) reaction of 1H-indene-1,2,3-triones with internal alkynes was realized using Ru and Co catalysts. 2-(2-Oxo-1,2-diphenylethylidene)-1H-indene-1,3(2H)-dione derivatives were obtained a catalyst, whereas S-alkyl 2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2-phenylethanethioates prepared catalyst. These transformations led to the synthesis α,β-unsaturated carbonyl compounds broad substrate scope, excellent regiocontrol, gram-scale amenability. This catalytic strategy or catalyst has rarely been described for other established CAM

Language: Английский

Citations

1
Copper‐Mediated Selective Multiple Inert Chemical Bonds Cleavage for Cyanation of Indoles via Tandem Carbon and Nitrogen Atom Transfer DOI
Shimin Xie, Fangfang Cai,

Lixin Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(19), P. 2299 - 2304

Published: May 22, 2024

Comprehensive Summary The activation of inert chemical bonds is an exciting area research in chemistry because it enables the direct utilization readily available starting materials and promotes atom‐ step‐economic synthesis. Undoubtedly, selectively activating transforming multiple even more intriguing demanding task synthetic chemistry. However, due to its inherent complexity extreme challenges, this endeavour rarely accomplished. We report a copper‐mediated complete cleavage selective transformation three easily feedstocks, i.e ., sp 2 C—H bond indoles, 3 one C—N methyl carbon atom TMEDA, C≡N triple CH CN. This reaction proceeds via tandem nitrogen transfer, allows for efficient cyanation presenting simple alternative synthesizing 3‐cyanoindoles.

Language: Английский

Citations

1