Three-component synthesis of tetrasubstituted pyrroles by condensation with amines and arylglyoxals

Kolos, N. N.; Zubar, Viktoriya V.; Omelchenko, Irina V.; Мусатов, Владимир И.

doi:10.1007/s10593-016-1869-8

Cited by 11 publications

(4 citation statements)

References 25 publications

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“…. [94][95][96] Chen developed a one-pot procedure involving the Blaise reaction between nitriles and -bromo esters in the presence of zinc, followed by addition of arylglyoxal monohydrates 197. 97 This reaction proceeds through formation of -enaminone 199, which subsequently undergoes nucleophilic addition with the arylglyoxal 197; intramolecular cyclization and dehydration of the resulting intermediate 200 gives the pyrrole 198…”

Section: Review Synthesis 22)mentioning

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: Review Synthesis 22)mentioning

confidence: 99%

Recent Advancements in Pyrrole Synthesis

Philkhana¹,

Badmus²,

Reis³

et al. 2021

Synthesis

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“…A new range of polysubstituted NH‐free pyrroles 83 was produced in high yields (Scheme 26). [26] Kolos and colleagues [27] developed a very efficient two‐component condensation between arylglyoxal 84 and 3‐aminocrotonate 85 . The respective ethyl 5‐aryl‐4‐hydroxy‐2‐methyl‐(1 H )‐pyrrole‐3‐carboxylates 86 were received in moderate yields (Scheme 27).…”

Section: Intra(inter)molecular and Related Reactionsmentioning

confidence: 99%

Recent Advances for the Synthesis of N‐Unsubstituted Pyrroles

et al. 2021

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Pyrroles are an interesting class of heterocyclic compounds due to their widespread use both in medical chemistry and in the chemistry of new materials. Search and development of new effective methods for the synthesis of the pyrrole ring is an urgent task. Along with this, the systematization of already known synthesis methods is an equally important task. Herein, we focused on the results of the synthesis of NH‐pyrroles that have been obtained since 2015.

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“…88 A convenient method for the synthesis of polysubstituted pyrrole scaffolds has been reported by Kolos and co-workers. 89 Refluxing of arylglyoxals 4, acetoacetic ester or its derivatives 52, and substituted anilines 8 in methanol with added catalytic amounts of acetic acid was found to result in precipitation of substituted pyrroles 51 or 53 from the hot reaction mixture after 30 min (Scheme 17). Scheme 17.…”

Section: Synthesis Of Monocyclic Pyrrolesmentioning

confidence: 99%

“…One-pot reaction of substituted pyrroles. 89 Liu et al reported the highly efficient annulation of enaminones 27 with arylglyoxals 4 and indoles 25', thiophenol 54 or arylamines 8'', yielding fully substituted pyrroles 55-57 via three-component domino reactions involving indolisation and thiolation processes (Scheme 18). 90 Scheme 18.…”

Section: Synthesis Of Monocyclic Pyrrolesmentioning

confidence: 99%

Recent advances in the synthesis of pyrroles via multicomponent reactions using arylglyoxals

Javahershenas¹,

Arlan²,

Prager³

et al. 2020

Arkivoc

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Pyrrole is widely known as an active pharmacophore. This core framework plays an important role in several natural and biological products. Due to its properties, developing such scaffolds has attracted much attention. The accessibility of these role-playing heterocyclic motifs via easy, high efficiency and developed methodologies is of interest and value in the creation of new heterocyclic compounds. This review highlights the broad range of applications of arylglyoxals in the synthesis of pyrrole derivatives via multicomponent reactions over the period 2010-2019.

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Three-component synthesis of tetrasubstituted pyrroles by condensation with amines and arylglyoxals

Cited by 11 publications

References 25 publications

Recent Advancements in Pyrrole Synthesis

Recent Advancements in Pyrrole Synthesis

Recent Advances for the Synthesis of N‐Unsubstituted Pyrroles

Recent advances in the synthesis of pyrroles via multicomponent reactions using arylglyoxals

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