Solvent-free synthesis of polysubstituted pyrroles catalyzed by ZnO nanorods

Sabbaghan, Maryam; Sanaeishoar, Haleh; Ghalaei, Azam; Sofalgar, Pegah

doi:10.1007/s13738-015-0697-6

Cited by 11 publications

(3 citation statements)

References 42 publications

(37 reference statements)

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“…This process consisted of the ZnO nanorods (ZnO-NRS)-catalyzed reactions between primary alkylamines, dialkyl acetylenedicarboxylates, and 2-chloro-1,3-dicarbonyl compounds at 70 °C under solvent-free conditions (Scheme 16 ). 21…”

Section: Synthesis Of Acyclic and Monocyclic Compoundsmentioning

confidence: 99%

Acetylenic Esters in Organic Synthesis

Hajinasiri¹

2022

Synlett

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Activated acetylenic substrates such as acetylenic esters and alkyl propiolates are very important in organic synthesis. Due to their electron deficiency, these compounds are widely used in combinatorial and multicomponent reactions, enabling the synthesis of a large variety of novel compounds. In addition, these substrates are powerful Michael acceptors and convenient dienophiles and dipolarophiles in Diels–Alder and 1,3-dipolar cycloaddition reactions. The addition of different nucleophiles, primarily phosphorus, nitrogen or sulfur, to the triple bonds of these substrates produces key intermediates, such as Tebby and Huisgen zwitterions, which can lead to designing pathways toward the generation of spirocyclic and polycyclic compounds. This account highlights recent studies on the chemistry of acetylenic esters and their applications in organic synthesis.1 Introduction2 Synthesis of Acyclic and Monocyclic Compounds3 Synthesis of Spirocyclic Compounds4 Synthesis of Polycyclic Compounds5 Conclusion

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Section: Synthesis Of Acyclic and Monocyclic Compoundsmentioning

confidence: 99%

Acetylenic Esters in Organic Synthesis

Hajinasiri¹

2022

Synlett

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“…Some reported methods for the synthesis of penta‐substituted pyrroles include acid‐catalyzed Paal‐Knorr pyrrole reaction, [9] base‐promoted synthesis from pre‐functionalized amides, [10] transition metal‐catalyzed strategies involving pre‐synthesized precursors using Cu, [11] Ag, [12] Au, [13] or Pd salts [14] . Penta‐substituted pyrroles can also be generated by employing heterogeneous catalysts like ZnO nanorods, [15a] and double surfactant‐modified magnetic nanocatalyst [15b] . There were several drawbacks associated with these strategies like use of metals as catalysts or pre‐synthesized catalysts, employment of stoichiometric amounts of base/reagents, and elaborate procedures for the preparation of starting materials.…”

Section: Introductionmentioning

confidence: 99%

TBAI‐Catalyzed, TBHP‐Mediated Modular Three‐Component Cascade Towards Highly Functionalized Pyrrole via [3+2] Annulation

Gnanaoli,

Rajkumar,

Gopal

et al. 2024

Eur J Org Chem

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A facile, one‐pot sequential synthesis of highly substituted pyrrole employing TBAI/TBHP has been developed from readily available precursors. β‐Enaminones generated in situ from β‐ketoesters and primary amines react sequentially with electron‐deficient alkynes via a radical pathway to form the penta‐substituted pyrroles in moderate to good yields. This strategy for the synthesis of highly functionalized pyrroles can be scaled up and shows tolerance to a variety of amines.

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“…An analogous reaction has been reported using ZnO nanoparticle catalyst. 31 In that work, only acetylene dicarboxylates were used as alkyne substrates and heating was employed. Also Scheme 3 respectively, in CDCl 3 using TMS as internal standard.…”

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confidence: 99%

Fe3O4 nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 1H-indole and 1H-pyrrole derivatives

Babaei

Hossaini

Besheli

et al. 2016

Chem Heterocycl Comp

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Magnetic Fe 3 O 4 nanoparticles as a heterogeneous catalyst were found to be efficient for the synthesis of a series of pyrrole and indole derivatives using three-component reactions of primary amines, 1,3-dicarbonyl compounds, and activated acetylenic compounds under solvent-free conditions at room temperature. The present protocol offers the advantages of clean reaction, short reaction time, high yield, easy purification, and affordability of the catalyst.

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Solvent-free synthesis of polysubstituted pyrroles catalyzed by ZnO nanorods

Cited by 11 publications

References 42 publications

Acetylenic Esters in Organic Synthesis

Acetylenic Esters in Organic Synthesis

TBAI‐Catalyzed, TBHP‐Mediated Modular Three‐Component Cascade Towards Highly Functionalized Pyrrole via [3+2] Annulation

Fe3O4 nanoparticles as an efficient and reusable catalyst for the solvent-free synthesis of 1H-indole and 1H-pyrrole derivatives

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