4.2 Article

One-pot multicomponent synthesis of highly substituted piperidines using p-toluenesulfonic acid monohydrate as catalyst

Journal

MONATSHEFTE FUR CHEMIE
Volume 143, Issue 6, Pages 939-945

Publisher

SPRINGER WIEN
DOI: 10.1007/s00706-011-0671-7

Keywords

Heterocycle; Piperidine; Multicomponent reaction; Homogeneous catalyst; p-TsOH center dot H2O

Funding

  1. Research Council of the University of Sistan and Baluchestan

Ask authors/readers for more resources

p-Toluenesulfonic acid monohydrate (p-TsOH center dot H2O) is a highly effective and efficient catalyst for the one-pot multicomponent coupling of aldehydes, amines, and beta-ketoesters in EtOH at ambient temperature to give highly functionalized piperidines in high yields. This one-pot reaction has some important advantages such as the easy workup procedure, simple and readily available precursors, nontoxic and inexpensive catalyst, and good to high yields.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.2
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Organic

Design and Synthesis, Antimicrobial Activities of 1,2,4-Triazine Derivatives as Representation of a New Hetrocyclic System

Maryam Shokoohian, Nourallah Hazeri, Malek Taher Maghsoodlou, Mojtaba Lashkari

Summary: New 1,2,4-triazine derivatives, as biologically active heterocyclics, were synthesized in the presence of acetic acid as a result of the reaction of pyridine-2-(1H)-one derivatives with 1,2-dicarbonyl compounds at 50 degrees C, and their biological properties were also investigated.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

Article Chemistry, Organic

Comprehensive Kinetics and a Mechanistic Investigation on the Biological Active Pyrano[2,3-C]Pyrazole Core in the Presence of Both Eco-Friendly Catalyst and Solvent: Experimental Green Protocol

Sadegh Talaiefar, Sayyed Mostafa Habibi-Khorassani, Mehdi Shaharaki

Summary: The full chemical kinetics of a four-component condensation reaction for the synthesis of pyranopyrazoles has been investigated spectrally. The reactions involving ethyl acetoacetate, hydrazine hydrate, malononitrile, and various substituents of benzaldehyde were studied. The reaction with para electron-withdrawing substituted benzaldehyde showed the largest negative Delta S-double dagger value. The unfavorable Delta S-double dagger value was compensated by a favorable Delta H-double dagger value. This correlated with a faster reaction rate and a lower Delta G-double dagger value. The study also revealed the importance of resonance and inductive effects in stabilizing the reaction center with a strong electron-withdrawing group.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

Article Chemistry, Organic

Utilizing an Old Idea for the Three-Component Synthesis of Anthraquinone-Scaffold-Based Enaminodiones (2,2-Diacylethenamines)

Zahra Aelami, Malek Taher Maghsoodlou, Reza Heydari, Afshin Yazdani-Elah-Abadi

Summary: An efficient and novel synthetic protocol for constructing aminomethylene cycloalkane-1,3-diones based on anthraquinone scaffold has been developed. The green synthetic procedure involves amino-methylene bond formation and has been successful in a one-pot reaction at room temperature, yielding the desired products in good yields. The chemical structures of these compounds were identified using various analytical techniques, and their DNA binding activities were investigated using electronic absorption spectra UV-vis.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

Article Chemistry, Organic

The First Effort for the Preparation of Amidoalkyl Naphthoquinone Skeleton Based on Solvent-Free Multicomponent Reaction

Sara Zhaleh, Nourallah Hazeri, Mohammad Reza Faghihi, Malek Taher Maghsoodlou

Summary: In this study, medicinally important amidoalkyl naphthoquinones were synthesized via an eco-friendly and straightforward method. The one-pot multicomponent reaction successfully prepared the precursors of these natural compounds, which are of great significance in medicinal research. The synthesized compounds were characterized using various techniques.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

Article Chemistry, Organic

Uric Acid as a Naturally Biodegradable and Reusable Catalyst for the Convenient and Eco-Safe Synthesis of Biologically Active Pyran Annulated Heterocyclic Systems

Mojtaba Lashkari, Farzaneh Mohamadpour, Malek Taher Maghsoodlou, Reza Heydari, Nourallah Hazeri

Summary: A naturally biodegradable, reusable, and eco-safe catalyst called uric acid has been developed for the green, facile and economical one-pot synthesis of pyran annulated heterocyclic systems. This study provides insight into the reliability of the catalyst in aiding the formation of heterocyclic compounds. The method offers high atom economy, cleaner reaction profile, simple column-free work up condition, shorter reaction times, high to excellent yields, eco-safety, and high catalytic activity, making it an interesting alternative to multistep approaches.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

Article Energy & Fuels

Production of greener energy in microbial fuel cell with ceramic separator fabricated using native soils: Effect of lattice and porous SiO2

Marzieh Cheraghipoor, Davod Mohebbi-Kalhori, Meissam Noroozifar, Malek Taher Maghsoodlou

Summary: In this study, ceramic membranes with different compositions were fabricated and used as separators in microbial fuel cells (MFCs). The addition of SiO2 to the membrane had varying effects on MFCs performance, with significant improvements observed when 30% SiO2 was added to non-leached soil.
Article Chemistry, Organic

KF/CP Nanoparticles Promoted Three Component Green Synthesis of Chromene Derivatives

Samanehsadat Sharifi, Malek Taher Maghsoudlou, Nourallah Hazeri

Summary: This research utilized a green process to synthesize chromen derivatives using a one-pot reaction in water at a low temperature with the catalytic effect of KF/Clinoptilolite nanoparticles. The procedure has advantages such as short reaction time, excellent yield, and the ability to use various substrates.

POLYCYCLIC AROMATIC COMPOUNDS (2022)

Article Chemistry, Organic

Application of salicylic acid as an eco-friendly and efficient catalyst for the synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives

Majid Roozifar, Nourallah Hazeri, Homayoun Faroughi Niya

Summary: This study presents three eco-friendly, efficient, and convenient protocols for the one-pot synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives using salicylic acid as a catalyst under solvent-free conditions. The reported protocols offer advantages such as a nontoxic, neutral, and cheap catalyst, environmentally friendly conditions, easily isolatable products, short reaction times, simple methodology, and good yields.

JOURNAL OF HETEROCYCLIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Synthesis, characterization, and application of CoFe2O4@TRIS@sulfated boric acid nanocatalyst for the synthesis of 2-amino-3-cyanopyridine derivatives

Homayoun Faroughi Niya, Nourallah Hazeri, Malek Taher Maghsoodlou, Maryam Fatahpour

Summary: This research successfully synthesized a novel acidic nanocatalyst for the efficient synthesis of 2-amino-3-cyanopyridine derivatives. The nanocatalyst offers advantages such as simplicity of work-up, high stability, and environmental friendliness.

RESEARCH ON CHEMICAL INTERMEDIATES (2021)

Article Chemistry, Multidisciplinary

Facile synthesis of pyrazole derivatives using reusable Fe3O4@MCM-41-SO3H

Sarnanehsadat Sharifi, Malek Taher Maghsoudlou, Nourallah Hazeri

Summary: Fe3O4-MCM-41-SO3H was synthesized as a magnetically reusable Lewis acid catalyst for the cyclization reaction of 3-acylcoumarins or 3-chromonecarboxylic acid with arylhydrazine derivatives to synthesize pyrazoles in high yields under solvent-free conditions. It was characterized by FTIR, SEM, and XRD analyses.

CANADIAN JOURNAL OF CHEMISTRY (2021)

Article Chemistry, Physical

Vitamin B12 used as effective biocatalyst for the synthesis of pyrano[2,3-c]cromenes and pyrano[2,3-d]pyrimidines

Ghasem Marandi, Reyhaneh Nadernia, Nourallah Hazeri, Malek Taher Maghsoodlou

Summary: The synthesis of 3,4-dihydropyrano[2,3-c]chromene and pyrano[2,3-d]pyrimidine derivatives using vitamin B-12 as a catalyst in a one-pot reaction of malononitrile, benzaldehydes, and 4-hydroxycumarine or 1,3-dimethylbarbituric acid is reported and has gained attention in recent years.

IRANIAN JOURNAL OF CATALYSIS (2022)

Article Chemistry, Organic

An efficient solvent-free synthesis of pyrido[2,3-d]pyrimidine derivatives utilizing lactic acid as green and eco-friendly catalyst

Mohyeddin Safarzaei, Ebrahim Mollashahi, Mojtaba Lashkari, Malek Taher Maghsoodlou, Nourallah Hazeri

Summary: The synthesis of pyrido[2,3-d]pyrimidine derivatives using lactic acid as a catalyst at 90 degrees C in a solvent-free and one-pot procedure is described. The benefits include green and environmentally friendly reaction conditions, high yields, short reaction time, simple methodology, and easy workup.

INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY (2021)

No Data Available