Transition-metal-free synthesis of polysubstituted pyrrole derivatives via [4 + 1] annulation of β-keto acids (C1 synthon) and α,β-unsaturated imines

Leng, Jiaying; Xu, Hui; Jiang, Meng; Luo, Xiaoyan; Deng, Wei‐Ping

doi:10.1016/j.tet.2019.130709

Cited by 2 publications

(1 citation statement)

References 59 publications

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“…Various motifs of dicarbonyl compounds have been extensively utilized toward pyrrole synthesis. [83][84][85][86][87][88][89][90][91][92][93] As discussed in this section, this class of starting materials have enabled the development of a broad array of new synthetic reactions.…”

Section: Dicarbonyl Compoundsmentioning

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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Section: Dicarbonyl Compoundsmentioning

confidence: 99%

Recent Advancements in Pyrrole Synthesis

Philkhana¹,

Badmus²,

Reis³

et al. 2021

Synthesis

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Metal‐Free CH Functionalization for the Synthesis of Pyrrole, Pyridine, and Pyrimidine

Borah¹,

Borah²,

Banik³

2022

Handbook of CH-Functionalization

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Heterocycles receive great attention because of their versatile properties as pharmacophores. Among these heterocycles, the biological activities, reactions, and synthesis of pyrrole‐, pyridine‐, and pyrimidine‐containing molecules are most important as they serve as a field of research in heteroaromatic chemistry. These scaffolds not only have a great presence in a broad range of drug molecules but are also found as pervasive shreds of several vitamins, pharmaceutically important natural products, synthetic drug candidates, and biomolecules. In this article, we summarize a diverse range of metal‐free CH functionalization approaches for the synthesis of pyrrole, pyridine, pyrimidine, and their derivatives.

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Transition-metal-free synthesis of polysubstituted pyrrole derivatives via [4 + 1] annulation of β-keto acids (C1 synthon) and α,β-unsaturated imines

Cited by 2 publications

References 59 publications

Recent Advancements in Pyrrole Synthesis

Recent Advancements in Pyrrole Synthesis

Metal‐Free CH Functionalization for the Synthesis of Pyrrole, Pyridine, and Pyrimidine

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