Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

ACS Omega, Год журнала: 2022, Номер 7(42), С. 36945 - 36987

Опубликована: Окт. 10, 2022

1,2,3-Triazole scaffolds are not obtained in nature, but they still intensely investigated by synthetic chemists various fields due to their excellent properties and green routes. This review will provide a library of all routes used the past 21 years synthesize 1,2,3-triazoles derivatives using metal catalysts (such as Cu, Ni, Ru, Ir, Rh, Pd, Au, Ag, Zn, Sm), organocatalysts, metal-free well solvent- catalyst-free neat syntheses, along with mechanistic cycles, recyclability studies, solvent systems, reaction condition effects on regioselectivity. Constant developments indicate that help lead future organic synthesis useful for creating molecular libraries functionalized 1,2,3-triazoles.

Язык: Английский

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2H‐Azirines: Recent Progress in Synthesis and Applications

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(11)

Опубликована: Янв. 29, 2024

Abstract 2H ‐arizines are important three‐membered heterocycles in organic chemistry. Recently, many advances the synthesis and functionalization of have been reported. Neber rearrangement, isomerization isoxazole, oxidation enamine, C−H bond activation, decomposition vinyl azide, alkyne, multi‐step developed for efficient assembly ‐azirines. As versatile highly strained unsaturated heterocycles, ‐azirines can be used as distinctive building blocks towards significant functional groups, attracted extensive attention fabrication numerous heterocycles. Recent studies focused on [3+n] ring‐expansion reactions, nucleophilic addition C=N double or continuous followed by cyclization, ring‐opening to acyclic compounds, substitution sp 3 ‐C−H One most critical challenges is seeking a selective opening specific three bonds azirine circle, some what achieved basis metal catalyst, photocatalysis, combination catalyst photocatalysis. In this review, recent involving reactivity accompanied with breakthroughs summarized. The review mainly covers period from 2019 2023.

Язык: Английский

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Asymmetric Multicomponent Propargylations via Carbon Dioxide Shuttling and Fixation

ACS Catalysis, Год журнала: 2024, Номер 14(15), С. 11646 - 11656

Опубликована: Июль 22, 2024

Язык: Английский

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Each Interruption is an Opportunity: Novel Synthetic Strategies Explored Through Interrupted Click Reactions

Chemistry - A European Journal, Год журнала: 2024, Номер 30(20)

Опубликована: Фев. 26, 2024

Abstract The particular and unique mechanism of the copper‐catalyzed reaction between azides alkynes (CuAAC) has not only allowed for efficient synthesis 1,2,3‐trisubstituted 1,4‐triazoles in excellent yields under mild conditions, becoming quintessential click reaction, but it also enabled straightforward formation a metallocycle intermediate, copper triazolyl. This, suitable conditions able to suppress its protonolysis, can be used either creation new bicyclic triazolyl structures or generation novel three four‐component reactions. aim this review is rationalize unify all these transformations, which are collectively referred as “interrupted reactions”.

Язык: Английский

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Late-Stage Functionalization Strategies of 1,2,3-Triazoles: A Post-Click Approach in Organic Synthesis

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 18, 2025

The 1,2,3-triazole scaffolds are an important class of biologically privileged heterocyclic compounds with several key applications in chemistry, biology, medicine, agriculture, and material science. "postclick" functionalization 1,2,3-triazoles may emerge as a promising tactic for the construction molecular architectures therapeutics is considered to be growing area investigation. This interest extends beyond regioselective Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) method that involves trapping Cu(I)-triazole suitable precursors. In this Perspective, we highlight impact postclick strategies organic synthesis required late-stage hope emerging concept provide ample opportunities modern notable medicinal materials

Язык: Английский

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Synthesis of tetra-substituted Furfuryl alcohols by Cu/Rh relay catalysis

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155661 - 155661

Опубликована: Май 1, 2025

Язык: Английский

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Light-Driven N-Heterocyclic Carbene-Catalyzed Multi-Component Reaction for the Synthesis of β-Amino Ketones

Organic Letters, Год журнала: 2024, Номер 26(41), С. 8848 - 8853

Опубликована: Окт. 8, 2024

A N-heterocyclic carbene-catalyzed (NHC) three-component reaction involving

Язык: Английский

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Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 13, 2024

In this work, the annulation of acyl nitrene with alkynes is reported under photoredox/iron dual-catalysis for synthesis a series isoquninalin-2-ones. The reaction featured high regioselectivity and good generality. particular, resulting isoquinalin-2-ones could be structurally elaborated into several biologically interesting scaffolds. Mechanism investigation suggests that was ascribed to formal [4 + 2] cyclization. It believed represents an initial example preparing isoquinolin-1-ones from ferric peroxyl-catalyzed insertion.

Язык: Английский

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Copper-Catalyzed Coupling of N-Phenoxyacetamides and 2H-Azirines for Synthesis of α-Amino Oxime Ethers

Synthesis, Год журнала: 2023, Номер 55(20), С. 3393 - 3401

Опубликована: Май 19, 2023

Abstract Copper-catalyzed coupling reaction involving N-phenoxyacetamides and 2H-azirines is described, in which N–O C–N bonds are broken restructured. This protocol provides an efficient strategy for the highly regioselective synthesis of racemic α-amino oxime ethers. In addition, this can be used to modify natural products gram-scale compatible.

Язык: Английский

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Synthesis of 2‐Aminopyridine Derivatives via a Tandem CuAAC/Ring‐Cleavage/[4+2]‐Cycloaddition/Rearrangement Reaction Sequence

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3689 - 3694

Опубликована: Июнь 22, 2024

Abstract 2 H ‐Azirines are an important class of small‐ring heterocycle that have been employed as versatile synthetic building blocks. Herein, a one‐pot CuAAC/ring‐cleavage/[4+2]‐cycloaddition/rearrangement reaction sequence involving terminal ynones, sulfonyl azides and ‐azirines is reported leads to 2‐aminopyridine derivatives. In the first step, highly reactive N ‐sulfonyl α ‐acylketenimines generated, via CuAAC/ring‐cleavage process, from ynones these undergo inverse electron‐demand Diels–Alder cycloaddition reactions with form (isolable) 1,3‐oxazines themselves base‐promoted ring‐cleavage rearrangement afford title compounds.

Язык: Английский

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