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

и другие.

Heterocycles, Год журнала: 2023, Номер 106(8), С. 1385 - 1385

Опубликована: Янв. 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

Язык: Английский

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

и другие.

ChemistrySelect, Год журнала: 2025, Номер 10(5)

Опубликована: Фев. 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.

Язык: Английский

Процитировано

1
Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones DOI

Alexander Yu. Belyy,

Alena D. Sokolova,

Rinat F. Salikov

и другие.

Mendeleev Communications, Год журнала: 2025, Номер 35(2), С. 162 - 164

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

1
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

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10180 - 10196

Опубликована: Июль 4, 2024

Presented herein are novel syntheses of CF

Язык: Английский

Процитировано

9
Masters of Mediation: MN(SiMe3)2 in Functionalization of C(sp3)−H Latent Nucleophiles DOI
Ramdas Sreedharan, Thirumanavelan Gandhi

Chemistry - A European Journal, Год журнала: 2024, Номер 30(29)

Опубликована: Март 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.

Язык: Английский

Процитировано

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

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(2), С. 1235 - 1240

Опубликована: Янв. 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.

Язык: Английский

Процитировано

4
Photoredox-Enabled Deconstructive [5 + 1] Annulation Approach to Isoquinolones from Indanones in Water DOI

Yuanyuan Fu,

Hui Liang,

Yanju Lu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3043 - 3047

Опубликована: Апрель 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.

Язык: Английский

Процитировано

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

Yuanyuan Fu,

Hui Liang,

F. Li

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 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.

Язык: Английский

Процитировано

0
Copper-Catalyzed Three-Component Tandem Cyclization for One-Pot Synthesis of Indole-Benzofuran Bis-Heterocycles DOI
Peng Ma, Yuhang Wang, Jianhui Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 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.

Язык: Английский

Процитировано

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

и другие.

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3164 - 3168

Опубликована: Март 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

Язык: Английский

Процитировано

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

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(19), С. 2299 - 2304

Опубликована: Май 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.

Язык: Английский

Процитировано

1