Vitamin B1 as a metal-free organocatalyst for greener Paal–Knorr pyrrole synthesis

Darabi, Hossein Reza; Aghapoor, Kioumars; Farahani, Abbas Darestani; Mohsenzadeh, Farshid

doi:10.1007/s10311-012-0361-7

Cited by 28 publications

(10 citation statements)

References 47 publications

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“…Pyrrole and its derivatives are a class of important five-membered nitrogen heterocyclic compounds, which can be synthesized by condensation from 1,4-dicarbonyl compounds, known as Paal-Knorr reaction. Though a variety of methods have been developed for pyrrole synthesis, Paal-Knorr condensation still remains the most widely used approach 1,2 . As is well known, the intermediates of an organic reaction may vary significantly depending on reaction conditions 3 .…”

Section: Introductionmentioning

confidence: 99%

Real-time monitoring of the reaction between aniline and acetonylacetone using extractive electorspray ionization tandem mass spectrometry

Zhang

Miao-rong

et al. 2019

Sci Rep

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In this work an on-line monitoring method was developed to study the mechanism of acetic acid catalyzed reaction between aniline and acetonylacetone using extractive electorspray ionization-tandem mass spectrometry (EESI-MS). The signals of reactants, intermediates and various byproducts were continuously detected as a function of reaction time. The chemical assignment of each signal was done via multi-stage collision induced dissociation (CID) analysis, and the reaction mechanism between aniline and acetonylacetone was deduced based on the generated molecular ions and fragment ions. The results indicate that on-line EESI-MS is an effective technique for the real time analysis of chemical reactions. EESI avoids off-line sample pretreatment and provides “soft” ionization, which allows direct analysis of various analytes at molecular level.

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Section: Introductionmentioning

confidence: 99%

Real-time monitoring of the reaction between aniline and acetonylacetone using extractive electorspray ionization tandem mass spectrometry

Zhang

Miao-rong

et al. 2019

Sci Rep

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“…All of the products were characterized by a comparison of their spectroscopic data with those of authentic samples [38][39][40]44].…”

Section: Methodsmentioning

confidence: 99%

“…Taking into account the importance of MCM-41 mesoporous molecular sieves as potential solid catalysts for the synthesis of N-containing heterocycles and our interest in the development of greener protocols for N-heterocyclic condensation [38][39][40], we decided to explore the viability of using MCM-41 to promote the Paal-Knorr pyrrole synthesis (Scheme 1) that, to the best of our knowledge, has not been reported yet.…”

Section: Introductionmentioning

confidence: 99%

Catalytic activity of the nanoporous MCM-41 surface for the Paal–Knorr pyrrole cyclocondensation

Aghapoor¹,

Amini

Jadidi

et al. 2015

Zeitschrift Für Naturforschung B

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The investigation of different oxide surfaces revealed that nanoporous silica (MCM-41) had the best catalytic activity for Paal-Knorr pyrrole synthesis. Despite the same composition, MCM-41 proved to be more effective than SiO 2 itself, probably due to a significantly higher surface area of the SiO 2 nanopores. The important features of this "clean" solvent-free protocol are the ease of recovery and the reuse of the catalyst for several cycles, operational simplicity, and easy product isolation and purification.

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“…Các sản phẩm sau khi cô lập được định danh bằng GC-MS và 1 H-NMR và 13 C-NMR, kết quả dữ liệu phổ được so sánh và thấy tương hợp với các dữ liệu đã được công bố: 2,5-Dimethyl-1-phenyl-1H-pyrrole 4, [24][25][26][27][28] (1) Abstract-The ionic liquid supported on magnetic nanoparticles ( -Fe2O3@SiO2-IL-ZnxCly) was found to be an effective catalyst for the Paal-Knorr reaction. The condensation of aromatic amine and acetonylacetone under solvent-free sonication afforded the desired pyrrole derivatives in high yields.…”

Section: Vật Liệu Và Phương Phápunclassified

Ionic liquid supported on magnetic nanoparticles (-Fe2O3@SiO2-IL-ZnxCly) as the green catalyst for the Paal-Knorr reaction

Nguyen

Tran

2019

Sci. Tech. Dev. J. - Nat. Sci.

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The ionic liquid supported on magnetic nanoparticles ( -Fe2O3@SiO2-IL-ZnxCly) was found to be an effective catalyst for the Paal–Knorr reaction. The condensation of aromatic amine and acetonylacetone under solvent-free sonication afforded the desired pyrrole derivatives in high yields. The pyrrole derivatives was isolated in yield with a environmentally friendly process. The structure of products was determined by modern methods such as nuclear magnetic resonance spectroscopy (1H and 13C NMR), high resolution mass spectrometry (HR-ESI-MS) or gas chromatography-mass spectrometry (GS-MS). Moreover, the catalyst could be easily recovered by magnetic separation and reused for five times without significant loss of the catalytic activity.

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Vitamin B1 as a metal-free organocatalyst for greener Paal–Knorr pyrrole synthesis

Cited by 28 publications

References 47 publications

Real-time monitoring of the reaction between aniline and acetonylacetone using extractive electorspray ionization tandem mass spectrometry

Real-time monitoring of the reaction between aniline and acetonylacetone using extractive electorspray ionization tandem mass spectrometry

Catalytic activity of the nanoporous MCM-41 surface for the Paal–Knorr pyrrole cyclocondensation

Ionic liquid supported on magnetic nanoparticles (-Fe2O3@SiO2-IL-ZnxCly) as the green catalyst for the Paal-Knorr reaction

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