Cu(II)-Catalyzed C–H Amidation/Cyclization of Azomethine Imines with Dioxazolones via Acyl Nitrenes: A Direct Access to Diverse 1,2,4-Triazole Derivatives

Organic Letters, Journal Year: 2022, Volume and Issue: 24(2), P. 613 - 618

Published: Jan. 3, 2022

We report a Cu(II)-catalyzed C-H amidation/cyclization of azomethine imines with dioxazolones as acyl nitrene transfer reagents under additive- and ligand-free conditions. An array 1,2,4-triazolo[1,5-a]pyridine derivatives were afforded in moderate to good yields excellent functional group tolerance. In addition, scale-up reaction photoluminescence properties discussed.

Language: Английский

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Rh(iii)-catalyzed cascade annulation reaction of N,N-dimethyl enaminones with iodonium ylides to give substituted isocoumarins

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(26), P. 12274 - 12278

Published: Jan. 1, 2023

A wide variety of isocoumarin derivatives are easily constructed via a Rh( iii )-catalyzed C–H bond activation/annulation cascade reaction.

Language: Английский

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One-step synthesis of cyanated pyrazolo[1,5-a]pyridines utilizing N-aminopyridines as a 1,3-dipole and a nitrogen source

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(12), P. 2892 - 2897

Published: Jan. 1, 2023

By utilizing the dual reactivity function of N -aminopyridinium ylides, we developed a direct [3 + 2]-cycloaddition ylides and ynals to build pyrazolo[1,5- ]pyridine core while introducing cyano group.

Language: Английский

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Isoquinolone Syntheses by Annulation Protocols

Catalysts, Journal Year: 2021, Volume and Issue: 11(5), P. 620 - 620

Published: May 11, 2021

Isoquinolones (isoquinolin-1(2H)-ones) are one of the important nitrogen-heterocyclic compounds having versatile biological and physiological activities, their synthetic methods have been recently developed greatly. This short review illustrates significant advances in construction isoquinolone ring with atom- step-economy, focusing on intermolecular annulation protocols intramolecular cyclization presence a variety catalyst systems. The syntheses isoquinolone-fused rings also included.

Language: Английский

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Looking deep into C–H functionalization: the synthesis and application of cyclopentadienyl and related metal catalysts

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(19), P. 3101 - 3121

Published: Jan. 1, 2022

This feature review is focused on recent key applications of commonly used transition-metal Cp-type catalysts for C–H bond functionalizations.

Language: Английский

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Transition metal- and oxidant-free [3 + 2] cyclization of azomethine imines utilizing vinylene carbonate as dual synthons

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(9), P. 2529 - 2533

Published: Jan. 1, 2022

A transition metal- and oxidant-free C–C/C–N annulation of azomethine imines with vinylene carbonate as dual synthons under simple reaction conditions is described herein.

Language: Английский

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Transition-metal-free synthesis of 4-amino isoquinolin-1(2H)-ones via a tandem reaction of arynes and oxazoles

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(6), P. 1550 - 1555

Published: Jan. 1, 2022

A facile and transition-metal-free method for the synthesis of 4-amino isoquinolin-1(2 H )-ones has been developed.

Language: Английский

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Recent advances in synthesis of isocoumarins: An overview

Tetrahedron, Journal Year: 2023, Volume and Issue: 150, P. 133740 - 133740

Published: Nov. 12, 2023

Language: Английский

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Rhodium‐Catalyzed C–H Bond Annulation for the Synthesis of 5‐ and 6‐Membered N‐Heterocyclic Building Blocks

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 17, 2024

Abstract The sustainable preparation of N ‐heterocycles is one the most active research areas owing to their predominance as synthetics building blocks with extensive applications in organic, pharmaceutical, and material chemistry fields. Among various catalytic protocols, C−H bond functionalization concomitant C−N formation, so‐called annulation, has become routes access because it starts from low‐functionalized materials generates a limited amount waste, all respecting concept atom economy. Rhodium complexes often catalyze these reactions. This review focuses on synthesis 5‐ 6‐membered ring ‐containing heterocycles such indoles, pyrroles, indolines, (iso)quinolinones, dihydroquinolines, pyrrolidones readily available starting materials, an emphasis novel cascade synthetic methodologies via C−N/C−C well mechanisms reactions, especially oxidation steps. We hope this will help researchers looking prepare minimum steps those who want develop new based activation/functionalizations.

Language: Английский

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Recent Advances in the Synthesis of Nitrogen‐Containing Heterocycles Based on Hydrazine‐Directed C−H Bond Activation/Annulation Reactions

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

Published: Feb. 21, 2025

Abstract Nitrogen‐containing heterocyclic compounds are the core skeletons of many natural products, bioactive molecules and drugs, transition metal‐catalyzed hydrazine‐directed C−H bond activation/annulation reactions is one effective methods for synthesis nitrogen‐containing compounds. In this review, important research progress activation reviewed according to size constructed heterocycles, substrate scope reaction mechanism discussed in detail, limitations future development prospects summarized outlooked.

Language: Английский

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