Synthesis of Polysubstituted Pyrroles through the Tandem 1,3‐Addition/5‐<i>endo</i>‐<i>dig</i> Cyclization of 1‐(1‐Alkynyl)cyclopropyl Imines

Urbanaitė, Aurelija; Čikotienė, Inga

doi:10.1002/ejoc.201600985

Cited by 13 publications

(1 citation statement)

References 63 publications

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“…For example, Čikotienė described the reaction of 1-(alk-1-ynyl)cyclopropyl imines 80 with various compounds containing polarized covalent bonds (EX) to produce pyrroles 81. 51 The mechanism of this reaction is proposed though activation of alkyne with EX, resulting in the fragmentation of the cyclopropyl ring and 5membered pyrrole cyclization by the imine moiety.…”

Section: Reagent-driven Synthesismentioning

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: Reagent-driven Synthesismentioning

confidence: 99%

Recent Advancements in Pyrrole Synthesis

Philkhana¹,

Badmus²,

Reis³

et al. 2021

Synthesis

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The Construction of Nitrogen‐Containing Heterocycles from Alkynyl Imines

Shan

Zhao

et al. 2020

Adv Synth Catal

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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 the recent advances in the synthesis of nitrogen‐containing heterocycles via the cyclization of alkynyl imines. By using this protocol, a variety of nitrogen‐containing heterocycles, mainly including four‐, five‐, six‐, and seven‐membered nitrogen‐containing heterocycles, aza‐spirocycles, and fused aza‐heterocycles, could be obtained efficiently under mild conditions. Additionally, mechanistic features of these transformations are also discussed.

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Transition Metal‐Catalyzed and Metal‐Free Cyclization Reactions of Alkynes with Nitrogen‐Containing Substrates: Synthesis of Pyrrole Derivatives

Neto

Zeni

2020

ChemCatChem

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This review describes the efforts in the synthesis of pyrrole derivatives using the reaction of alkynes with nitrogen‐compounds under transition metal‐catalyzed and metal‐free conditions, in the past decade. We initially focused on the methods of preparation of pyrrole derivatives using reactions catalyzed by transition metal. In this part, we described the syntheses of 1‐pyrrolines, 2‐pyrrolines, 3‐pyrrolines, pyrroles, and pyrrolidines following an alphabetical order of the transition metal used for the synthesis. Subsequently, we presented the synthesis of these pyrrole derivatives under metal‐free conditions.

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Synthesis of Polysubstituted Pyrroles through the Tandem 1,3‐Addition/5‐endo‐dig Cyclization of 1‐(1‐Alkynyl)cyclopropyl Imines

Cited by 13 publications

References 63 publications

Recent Advancements in Pyrrole Synthesis

Recent Advancements in Pyrrole Synthesis

The Construction of Nitrogen‐Containing Heterocycles from Alkynyl Imines

Transition Metal‐Catalyzed and Metal‐Free Cyclization Reactions of Alkynes with Nitrogen‐Containing Substrates: Synthesis of Pyrrole Derivatives

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