Synthesis of Polysubstituted 3-Amino Pyrroles via Palladium-Catalyzed Multicomponent Reaction

Peng, Jianwen; Gao, Yang; Zhu, Chuanle; Liu, Bifu; Gao, Yuan; Hu, Miao; Wu, Wanqing; Jiang, Huanfeng

doi:10.1021/acs.joc.7b00098

Cited by 53 publications

(19 citation statements)

References 59 publications

(21 reference statements)

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“…We expect that use of 4,4’‐diacyl biphenyl to construct bis‐pyrroles will certainly attract the attention of synthetic and medicinal chemists. In addition to this, pyrroles such as ( 4 y ) could be transformed to dihydropyrrolo[3,2‐ b ]indoles using intra‐molecular Buchwald‐Hartwig cross coupling conditions.…”

Section: Methodsmentioning

confidence: 99%

Iodine‐Promoted One‐pot Synthesis of Highly Substituted 4‐Aminopyrroles and Bis‐4‐aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines

et al. 2018

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An iodine-promoted one-pot synthesis of functionally diverse and highly substituted 4-aminopyrroles directly from aryl methyl ketones, arylamines, and enamines was developed. The reaction involves in-situ oxidation of aryl methyl ketone to glyoxal, subsequent imine formation by aniline, followed by nucleophilic addition of enamine, and cyclization to afford highly substituted 4-aminopyrroles. This reaction involved the formation of two CÀN bonds and one CÀC bond by a formal [1 + 1 + 3] annulation approach. The present method provides an interesting framework of two 4aminopyrrole units directly attached to a biphenyl core by the reaction of 4,4'-diacyl biphenyl, amine, and enamine groups. This Hantzsch-type one-pot reaction provides diverse 4-aminopyrroles, which could be useful in medicinal/material chemistry.

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Section: Methodsmentioning

confidence: 99%

Iodine‐Promoted One‐pot Synthesis of Highly Substituted 4‐Aminopyrroles and Bis‐4‐aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines

et al. 2018

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“…Jiang and Wu developed a palladium-catalyzed three-component reaction using aryl halides, isocyanides, and N-tosylhydrazones 169 to assemble substituted 3-aminopyrroles. 77 The key mechanistic steps in this reaction begin with oxidative addition of Pd(0) to aryl halides, followed by double isocyanide insertion to form iminopalladium 171. This species is then trapped by in situ generated diazo compound 172, formed as a result of decomposition of N-tosylhydrazones 169, to yield palladium-carbene complex 173.…”

Section: Scheme 18 From Cyanidesmentioning

confidence: 99%

Recent Advancements in Pyrrole Synthesis

Philkhana¹,

Badmus²,

Reis³

et al. 2021

Synthesis

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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 that can be found in numerous compounds of biological and material significance. Given its vast importance, pyrrole continues to be an attractive target for the development of new synthetic reactions. The contents of this article are organized by the starting materials, which can be broadly classified into four different types: substrates bearing π-systems, substrates bearing carbonyl and other polar groups, and substrates bearing heterocyclic motifs. Brief discussions on plausible reaction mechanisms for most transformations are also presented.1 Introduction2 From π-Systems2.1 Alkenes2.2 1,6-Dienes2.3 Allenes2.4 Alkynes2.5 Propargylic Groups2.6 Homopropargylic Amines3 From Carbonyl Compounds3.1 Aldehydes3.2 Ketones3.3 Cyanides and Isocyanides3.4 Formamides3.5 β-Enamines3.6 Dicarbonyl Compounds4 From Polar Compounds4.1 Aminols4.2 Diols4.3 Organonitro Compounds5 From Heterocycles5.1 Münchnones5.2 Isoxazoles5.3 Carbohydrates5.4 trans-4-Hydroxy-l-prolines5.5 Pyrrolines6 Summary

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“…Pd-catalyzed reactions of propargyl carbonates, isocyanides, and alcohols or water In 2017, Jiang, Wu and co-workers [130] further developed a palladium-catalyzed approach for synthesis of multisubstituted 3-amino pyrroles via three-component tandem reaction (Scheme 93). This reaction was initiated with a double isocyanide insertions of a Pd complex generated by Pd catalyst and halide substrates.…”

Section: Scheme 92mentioning

confidence: 99%