Recent Advances on Pyrrole Synthesis through Different Annulation Modes

Xu, Xuetao; Chen, Jie; Zhang, Kun; Wu, Panpan; Wang, Shaohua

doi:10.6023/cjoc202005018

Cited by 16 publications

(3 citation statements)

References 121 publications

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“…For example, polysubstituted pyrroles are extensively used as key intermediates in synthesizing dyes, pharmaceuticals, perfumes, agrochemicals, photographic chemicals, and other organic compounds . Therefore, construction of the pyrrole ring and its further functionalization is always a hot topic in organic synthetic chemistry . Since its first synthesis in the 1880s, tremendous methods have been developed for the construction of this kind of privileged molecule.…”

Section: Introductionmentioning

confidence: 99%

Modular Synthesis of Tetrasubstituted Pyrroles through a Four-Component Cyclization Strategy Using Ammonium Salt as the Nitrogen Source

et al. 2023

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A four-component synthesis of tetrasubstituted pyrroles was developed under metal-free conditions. The pyrrole ring was formed in one pot through [2 + 1 + 1 + 1] condensation using ammonium salt as the nitrogen source. In this strategy, 1,4-naphthoquinones and maleimides were used as the versatile C2 fragments to provide substituted benzo[f]isoindole-4,9-diones and pyrrolo[3,4-c]pyrrole-1,3-diones, respectively. This work is highlighted by using ammonium salt as the nitrogen source, readily available starting materials and multibond formation (two C–C and two C–N bonds) in a single operation.

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Section: Introductionmentioning

confidence: 99%

Modular Synthesis of Tetrasubstituted Pyrroles through a Four-Component Cyclization Strategy Using Ammonium Salt as the Nitrogen Source

et al. 2023

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“…In industry, pyrrole mainly comes from the extraction of coal tar, the condensation reaction of furan and ammonia under high temperature, or the cascade cyclization reaction of acetylene, formaldehyde, and ammonia. In the laboratory, there are many efficient methods for the synthesis of pyrrole derivatives: i) Knorr reaction: the condensation of α-aminoketones or α-amino esters in the presence of zinc powder and sodium acetate; ii) Paal-Knorr reaction: the condensation of 1,4-dicarbonyl compounds and amines, catalyzed by formic acid in anhydrous alcohol; iii) Hantzsch reaction: the condensation of α-halogenated carbonyl compounds, β-dicarbonyl compounds and amines; and iv) the latest developed multicomponent tandem reactions and transition metal-catalyzed coupling reactions [30][31][32][33][34][35][36][37][38][39].…”

Section: Introductionmentioning

confidence: 99%

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

Liu¹,

Luo²,

Fu³

et al. 2021

Beilstein J. Org. Chem.

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Great progress has been made in the tandem annulation of enynes in the past few years. This review only presents the corresponding reactions of 1,3-enyne structural motifs to provide the functionalized pyridine and pyrrole derivatives. The functionalization reactions cover iodination, bromination, trifluoromethylation, azidation, carbonylation, arylation, alkylation, selenylation, sulfenylation, amidation, esterification, and hydroxylation. We also briefly introduce the applications of the products and the reaction mechanisms for the synthesis of corresponding N-heterocycles.

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“…Pyrroles are important N-heterocyclic motifs that play crucial roles in medicinal and materials chemistry. 1,2 Accordingly, significant research effort has been devoted to the discovery and development of methods for the synthesis of pyrroles, [3][4][5][6] notably those enabled by condensation chemistry including Paal-Knorr, 7 Hantzsch, 8 and Knorr 9 approaches. Multicomponent strategies for pyrrole synthesis are especially attractive given the potentially greater simplicity and accessibility of the starting materials.…”

mentioning

confidence: 99%

Two-Step, One-Pot Pyrrole Synthesis by Iron-Catalyzed Carboamination/Copper-Mediated Cyclization

Murphy

Richards

Applegate

et al. 2022

Synlett

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Herein we report a method for pyrrole synthesis via iron-catalyzed carboamination/copper-mediated cyclization that is completely regioselective for the formation of 1,2,4-trisubstituted products. This two-step, one-pot process offers significant improvements to previously reported conditions including the use of a readily available copper(I) source and a markedly less arduous experimental procedure. Exploration of the substrate scope reveals a variety of arylacetylenes undergo pyrrole formation to afford single isomer products. Isotopic labelling data points to a mechanism involving activation of the alkyne moiety by the copper(I) reagent during the cyclization step.

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Recent Advances on Pyrrole Synthesis through Different Annulation Modes

Cited by 16 publications

References 121 publications

Modular Synthesis of Tetrasubstituted Pyrroles through a Four-Component Cyclization Strategy Using Ammonium Salt as the Nitrogen Source

Modular Synthesis of Tetrasubstituted Pyrroles through a Four-Component Cyclization Strategy Using Ammonium Salt as the Nitrogen Source

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

Two-Step, One-Pot Pyrrole Synthesis by Iron-Catalyzed Carboamination/Copper-Mediated Cyclization

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Recent Advances on Pyrrole Synthesis through Different Annulation Modes

Cited by 16 publications

References 121 publications

Modular Synthesis of Tetrasubstituted Pyrroles through a Four-Component Cyclization Strategy Using Ammonium Salt as the Nitrogen Source

Modular Synthesis of Tetrasubstituted Pyrroles through a Four-Component Cyclization Strategy Using Ammonium Salt as the Nitrogen Source

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

Two-Step, One-Pot Pyrrole Synthesis by Iron-Catalyzed ­Carboamination/Copper-Mediated Cyclization

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Two-Step, One-Pot Pyrrole Synthesis by Iron-Catalyzed Carboamination/Copper-Mediated Cyclization