Recent Advancements in Pyrrole Synthesis

Synthesis, Journal Year: 2021, Volume and Issue: 53(09), P. 1531 - 1555

Published: March 17, 2021

This review article features selected examples on the synthesis of functionalized pyrroles that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing aromatic heterocycle can be found in numerous compounds biological material significance. Given its vast importance, pyrrole continues to attractive target for development new synthetic reactions. The contents this are organized by starting materials, which broadly classified into four different types: substrates bearing π-systems, carbonyl other polar groups, heterocyclic motifs. Brief discussions plausible reaction mechanisms most transformations also presented.

Language: Английский

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Cyanation with isocyanides: recent advances and perspectives

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(12), P. 1546 - 1562

Published: Jan. 1, 2024

This review focuses on the cyanation of isocyanides with recent advances and perspectives.

Language: Английский

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The clean preparation of multisubstituted pyrroles under metal- and solvent-free conditions

Green Chemistry, Journal Year: 2019, Volume and Issue: 22(1), P. 118 - 122

Published: Nov. 29, 2019

A practical method for the clean preparation of multisubstituted pyrroles via an iodine-catalyzed multicomponent reaction under metal- and solvent-free conditions was developed. In gram-scale synthesis, can be easily collected through simple extraction.

Language: Английский

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Recent advances in the direct β-C(sp²)–H functionalization of enamides

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(8), P. 1504 - 1521

Published: Jan. 1, 2020

Recent advances in the direct β-C(sp²)–H functionalization of enamides, mainly including arylation, alkenylation, alkynylation, alkylation, acylation, sulfonylation, phosphorylation, and others, are reported.

Language: Английский

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Recent Advances in Palladium-Catalyzed Isocyanide Insertions

Molecules, Journal Year: 2020, Volume and Issue: 25(21), P. 4906 - 4906

Published: Oct. 23, 2020

Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function a CO-substitute palladium-catalyzed cross couplings. Over the past decades, isocyanides emerged practical and C1 building blocks, whose inherent N-substitution for rapid incorporation of nitrogeneous fragments wide variety products. Recent developments palladium catalyzed isocyanide insertion reactions significantly expanded scope applicability these imidoylative cross-couplings. This review highlights advances made this field over eight years.

Language: Английский

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The Construction of Nitrogen‐Containing Heterocycles from Alkynyl Imines

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 363(4), P. 906 - 923

Published: Dec. 25, 2020

Abstract Nitrogen‐containing heterocycles have attracted considerable attention due to their extensive applications in the fields of organic synthesis, pharmaceuticals, agrochemicals, and materials science. This review focuses on recent advances synthesis nitrogen‐containing via cyclization alkynyl imines. By using this protocol, a variety heterocycles, mainly including four‐, five‐, six‐, seven‐membered aza‐spirocycles, fused aza‐heterocycles, could be obtained efficiently under mild conditions. Additionally, mechanistic features these transformations are also discussed. magnified image

Language: Английский

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Ultrasound-assisted tandem synthesis of tri- and tetra-substituted pyrrole-2-carbonitriles from alkenes, TMSCN and N,N-disubstituted formamides

Chinese Chemical Letters, Journal Year: 2020, Volume and Issue: 31(12), P. 3241 - 3244

Published: July 9, 2020

Language: Английский

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Annulation of CF₃–Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles

Organic Letters, Journal Year: 2021, Volume and Issue: 23(19), P. 7407 - 7411

Published: Sept. 20, 2021

A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have obtained in 27–78% yield. This features a broad substrate scope generates dimethyl sulfoxide H2O as byproducts.

Language: Английский

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Triple-Consecutive Isocyanide Insertions with Aldehydes: Synthesis of 4-Cyanooxazoles

Organic Letters, Journal Year: 2023, Volume and Issue: 25(5), P. 849 - 854

Published: Jan. 27, 2023

An efficient TMSOTf-promoted selective triple consecutive insertions of tert-butyl isocyanide into aldehydes has been developed, affording pharmacological interesting 4-cyanooxazoles in high yields a one pot manner. The given method encompasses wide range substrates with serving as sources critical "CN" and "C–N═C" moieties. versatile transformations the resulting were demonstrated. key reaction intermediates for plausible mechanisms determined.

Language: Английский

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Divergent oriented synthesis (DOS) of aza-heterocyclic amides through palladium-catalyzed ketenimination of 2-iodo-N-(propa-1,2-dien-1-yl)anilines

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(6), P. 890 - 895

Published: Jan. 1, 2020

A palladium-catalyzed tandem reaction of N-(2-iodophenyl)-4-methyl-N-(propa-1,2-dien-1-yl)benzenesulfonamide with isocyanide is described to divergently produce aza-heterocyclic amides.

Language: Английский

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