Direct Catalytic Functionalization of Indazole Derivatives

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(18), P. 3768 - 3794

Published: May 28, 2020

Abstract Indazoles are a very important class of N‐containing heterocycles with wide range biological and medicinal properties. The presence different functionalities on indazole moieties enhances its activities. Hence, the preparation compounds bearing functional groups has gained significant interest to organic synthetic chemists. A large effort been made develop efficient new methods for functionalization indazoles. Direct catalytic is powerful tool facile synthesis derivatives due straightforwardness. This review summarizes developments direct functionalizations indazoles published in last two decades. magnified image

Language: Английский

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Regioselective hydroarylation and arylation of maleimides with indazoles via a Rh(iii)-catalyzed C–H activation

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(16), P. 3093 - 3097

Published: Jan. 1, 2020

Switchable Rh(iii)-catalyzed highly regioselective hydroarylation and oxidative arylation of maleimides with 2-arylindazoles via C–H activation have been demonstrated.

Language: Английский

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Recent advances in C–H functionalization of 2H-indazoles

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(39), P. 7746 - 7764

Published: Jan. 1, 2022

2H-Indazoles are one class of the most important nitrogen-containing heterocyclic compounds. The 2H-indazole motif is widely present in bioactive natural products and drug molecules that exhibit distinctive bioactivities. Therefore, much attention has been paid to access diverse derivatives. Among them, late-stage functionalization 2H-indazoles via C-H activation recognized as an efficient approach for increasing complexity diversity In this review, we summarized recent achievements 2H-indazoles, including C3-functionalization through transition metal-catalyzed or a radical pathway, ortho C2'-H remote at benzene ring 2H-indazoles.

Language: Английский

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Rh(III)-Catalyzed C–H Cyanation of 2H-Indazole with N-Cyano-N-phenyl-p-toluenesulfonamide

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(16), P. 10835 - 10845

Published: July 21, 2020

A Rh(III)-catalyzed direct cyanation of 2H-indazoles with N-cyano-N-phenyl-p-toluenesulfonamide has been realized via a chelation-assisted strategy. The methodology enables regioselective access to various ortho-cyanated phenylindazoles in good yields broad substrate scope and functional group compatibility. obtained cyanated indazoles could further be converted into other value-added chemicals. Importantly, the current protocol is featured several characteristics, including novel cyanating agent, regioselectivity, operational convenience.

Language: Английский

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Electrochemically promoted C-3 amination of 2H-indazoles

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 8(4), P. 754 - 759

Published: Dec. 11, 2020

A metal-free and external oxidant-free method for the C-3 amination of 2H-indazoles in good yields was developed under electrochemical conditions.

Language: Английский

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Rh(III)-Catalyzed Spiroannulation Reaction of N-Aryl Nitrones with 2-Diazo-1,3-indandiones: Synthesis of Spirocyclic Indole-N-oxides and Their 1,3-Dipolar Cycloaddition with Maleimides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3845 - 3858

Published: March 8, 2023

An efficient strategy for the preparation of spirocyclic indole-N-oxide compounds through a Rh(III)-catalyzed [4 + 1] spiroannulation reaction N-aryl nitrones with 2-diazo-1,3-indandiones as C1 synthons under extremely mild conditions is presented. From this reaction, 40 indole-N-oxides were easily obtained in up to 98% yield. In addition, title could be successfully used construction structurally intriguing maleimide-containing fused polycyclic scaffolds via diastereoselective 1,3-dipolar cycloaddition maleimides.

Language: Английский

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Electrochemical Regioselective C-3 Alkoxycarbonylation of 2H-Indazoles

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 23, 2025

This study describes an efficient electrochemical synthetic method for C-3 alkoxycarbonylation of 2H-indazoles with carbazates under constant current in undivided cell without the need external oxidants or metal catalysts. methodology exhibits broad functional group compatibility, affording products good yields. Easy scalability and drug diversification demonstrate efficacy applicability this protocol.

Language: Английский

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Controllable chemoselectivity in the reaction of 2H-indazoles with alcohols under visible-light irradiation: synthesis of C3-alkoxylated 2H-indazoles and ortho-alkoxycarbonylated azobenzenes

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(15), P. 4230 - 4236

Published: Jan. 1, 2021

A high chemoselectivity in the visible-light-induced reaction of 2H-indazoles with alcohols controlled by atmosphere was achieved, providing C3-alkoxylated and ortho-alkoxycarbonylated azobenzenes.

Language: Английский

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Rh(iii)-catalyzed substrate-dependent oxidative (spiro)annulation of isoquinolones with diazonaphthoquinones: selective access to new spirocyclic and oxepine-fused polycyclic compounds

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(23), P. 6598 - 6605

Published: Jan. 1, 2022

An efficient protocol for the selective synthesis of novel isoquinolone-containing spirocyclic and oxepine-fused polycyclic compounds via rhodium( iii )-catalyzed (spiro)annulation NH -isoquinolones with diazonaphthalen-2(1 H )-ones is reported.

Language: Английский

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Construction of Bridged Carbocycles and Heterocycles via Rh(III)-Catalyzed C–H Alkylation/Michael Addition of 2-Arylindoles with Quinone Monoacetals

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(14), P. 8910 - 8922

Published: June 16, 2020

A rhodium-catalyzed formal [4 + 5] annulation reaction of 2-arylindoles with quinone monoacetals for the selective preparation bridged nine-membered carbocyclic and heterocyclic compounds is developed. When 2-aryl substituted indoles are employed, this affords excellent indolyl C3 selectivity. On other hand, 2-aryl-3-substituted as substrates, exclusively formed via N1 annulation. Further transformations obtained products into new showcase synthetic potential protocol.

Language: Английский

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