Synthesis of 3H-pyrroles (microreview)

Belikov, М. Yu.; Ершов, О. В.

doi:10.1007/s10593-016-1877-8

Cited by 8 publications

(4 citation statements)

References 21 publications

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“…However, recent advances in the research on synthetic strategies for 2H-pyrroles have yet to be highlighted in review papers, although synthetic methods for 3Hpyrroles were outlined in a review in 2016. [13] Recent synthetic strategies for 2H-pyrroles can be classified into four categories (Figure 3): (1) catalytic dearomatization reactions of 1H-pyrroles, (2) oxidation of pyrroline or pyrrolidine skeletons, (3) ring constructions via intra-and intermolecular annulations, and (4) rearrangements using N-heterocycles. Noteworthy, mild reaction conditions could be achieved using transitionmetal catalysts, which would result in high synthetic efficiency and a broad substrate scope for 2H-pyrroles.…”

Section: Introductionmentioning

confidence: 99%

“…Over the past decades, significant advancements in 2 H ‐ and 3 H ‐pyrrole syntheses with increasing reaction efficiency and substrate scope have been achieved, particularly in catalytic asymmetric transformations. However, recent advances in the research on synthetic strategies for 2 H ‐pyrroles have yet to be highlighted in review papers, although synthetic methods for 3 H ‐pyrroles were outlined in a review in 2016 [13] . Recent synthetic strategies for 2 H ‐pyrroles can be classified into four categories (Figure 3): (1) catalytic dearomatization reactions of 1 H ‐pyrroles, (2) oxidation of pyrroline or pyrrolidine skeletons, (3) ring constructions via intra‐ and intermolecular annulations, and (4) rearrangements using N‐heterocycles.…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in Synthetic Methods for 2H‐Pyrroles

Choi,

Kim

2023

Adv Synth Catal

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The compound, 2H‐pyrrole, is a key scaffold contained in natural products, bioactive compounds, pharmaceuticals, and organic functional materials. However, the development of efficient synthetic strategies for 2H‐pyrroles is challenging. This is because 2H‐pyrroles, owing to their nonaromatic nature, are easily converted into the thermodynamically more stable 1H‐pyrroles. Recently, efficient and straightforward synthetic strategies for 2H‐pyrroles have been developed, including the dearomatization of 1H‐pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H‐pyrroles. In this review, we summarize the progress in the research on 2H‐pyrrole synthesis since 2000 and briefly discuss the synthesis reaction mechanisms.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Advances in Synthetic Methods for 2H‐Pyrroles

Choi,

Kim

2023

Adv Synth Catal

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“…Interestingly, between 2000 and 2020 over a dozen review articles have been published to summarize the various advancements that have been made to assemble this highly important molecular structure. [11][12][13][14][15][16][17][18][19][20][21][22][23][24] In this article, we wish to provide a brief survey on selected pyrrole syntheses that were published between 2014-2019. Upon examining literature precedents within this time span, we discerned that the various starting materials used in these new chemistries can be grouped broadly into four different types: substrates bearing -systems, substrates bearing carbonyl and other polar groups, and substrates bearing heterocyclic motifs ( Figure 2).…”

Section: Introductionmentioning

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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“…Nowadays, among non‐aromatic aza‐heterocycles, a particular attention is given to the chemistry of 3 H ‐indole motif, which is widely presented in natural products and biologically active compounds Meanwhile, the chemistry and applications of 3 H ‐pyrroles (cyclic azapentadienes), close in structure to the well‐explored 3 H ‐indoles, are still much less developed. The lack of simple synthetic approaches to this heterocyclic scaffold is the main stumbling block in this area, which has been significantly overcome during last years …”

Section: Introductionmentioning

confidence: 99%