Catalyst-free synthesis of fused 1,2,3-triazole and isoindoline derivatives via an intramolecular azide–alkene cascade reaction

Xie, Yuyang; Wang, Yingchun; He, Yan; Hu, Dachao; Wang, Hengshan; Pan, Ying‐Ming

doi:10.1039/c6gc01553k

Cited by 40 publications

(12 citation statements)

References 37 publications

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“…These studies have made a significant contribution to the synthesis of more efficient, simpler and more environmentally friendly techniques that are still needed for the synthesis of pyrrolo[1,2-a]quinolines. A highly efficient synthesis of pyrrolo[1,2-a]quinolines without catalysts was reported through dehydration, [3+2] cyclization of aldehydes and alkylating agents directly to 2-methylquinoline (Scheme 4) [47][48][49][50][51].…”

Section: Methodsmentioning

confidence: 99%

Basic approaches to the synthesis of pyrrolo[1,2-a]quinolines derivatives: a review

2019

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At the present stage of the development of organic and bioorganic chemistry, several basic approaches to the synthesis of pyrrolo[1,2-a]quinolines are known. These compounds are of interest to the researches primarily as bioregulators with a wide spectrum of biological activity. This review is an attempt to systematize and generalize literary data relating to the chemistry of pyrrolo[1,2-a]quinoline and its derivatives as important synthetic substrates and precursors for the design of biologically active substances. The main approaches to the synthesis of these compounds, consisting in various preparative methods for constructing a tricyclic base of pyrrolo[1,2-a]quinolone, were considered. The search for biologically active substances of this series is important and has a practical and theoretical significance.

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Section: Methodsmentioning

confidence: 99%

Basic approaches to the synthesis of pyrrolo[1,2-a]quinolines derivatives: a review

2019

VKhKhT

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“…A regioselective synthesis of 1,2,3‐triazole fused isoindole derivatives 272 from benzyl bromides bearing ortho‐substituted α,β‐unsaturated ketone 271 via intramolecular alkene‐azide cascade reaction under catalyst free conditions was established by Pan and group (Scheme 84). [87] The reaction was found to work efficiently in just DMF solvent at room temperature in open air. Various catalysts and even DMF in nitrogen atmosphere displayed no reaction or poorer yields.…”

Section: Synthesis Of Fused 123‐triazolesmentioning

confidence: 99%

Progress in the Synthesis of Fused 1,2,3‐Triazoles

et al. 2021

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Fused heterocycles display prodigious prominence in diverse field ranging from medicinal chemistry to material science and chemical biology to catalysis. Owing to biological importance, fused 1,2,3‐triazoles have gained much attention and hence, enormous efforts on its synthesis is given by the chemists. Diverse functionalized fused polycyclic 1,2,3‐triazole heterocycles have been designed using Huisgen's thermal intramolecular cycloaddition, copper catalyzed cycloaddition, bimetallic catalytic, greener and other miscellaneous approaches. Novel methodologies that use modified substrates such as ketones, enals, β‐keto esters, olefins, enones, C−H acids etc. in place of alkynes have been developed. Herein, synthetic methodologies to construct fused 1,2,3‐triazoles are briefly discussed.

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“…An example is given by the aziridination of olefins usually catalyzed by copper, rhodium, ruthenium, iron, or silver complexes, which is the methodology of choice for the preparation of this nitrogen-containing heterocycles [8,9]. The azides are exploited in heterocyclic synthesis as 1,3-dipoles with alkynes, alkenes, and nitriles in [3+2] dipolar cycloadditions to easily obtain 1,2,3-triazole and tetrazole derivatives, also according to the principle of the "click chemistry" [10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Transition Metal Catalyzed Azidation Reactions

et al. 2020

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A wide range of methodologies for the preparation of organic azides has been reported in the literature for many decades, due to their interest as building blocks for different transformations and their applications in biology as well as in materials science. More recently, with the spread of the use of transition metal-catalyzed reactions, new perspectives have also materialized in azidation processes, especially concerning the azidation of C–H bonds and direct difunctionalization of multiple carbon-carbon bonds. In this review, special emphasis will be placed on reactions involving substrates bearing a leaving group, hydroazidation reactions and azidation reactions that proceed with the formation of more than one bond. Further reactions for the preparation of allyl and vinyl azides as well as for azidations involving the opening of a ring complete the classification of the material.

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Catalyst-free synthesis of fused 1,2,3-triazole and isoindoline derivatives via an intramolecular azide–alkene cascade reaction

Abstract: A simple and efficient methodology has been developed for the regioselective synthesis of fused 1,2,3-triazole and isoindoline derivatives under catalyst free conditions.

Cited by 40 publications

References 37 publications

Basic approaches to the synthesis of pyrrolo[1,2-a]quinolines derivatives: a review

Basic approaches to the synthesis of pyrrolo[1,2-a]quinolines derivatives: a review

Progress in the Synthesis of Fused 1,2,3‐Triazoles

Transition Metal Catalyzed Azidation Reactions

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