The Recyclable Bronsted Acidic Liquid Resin Mediated Eco-benign Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones and 3,4-Dihydropyrimidin-2(1H)-thiones via  Biginelli Reaction

D. Parthiban; R. Joel Karunakaran; C. J. Magesh

doi:10.9734/IRJPAC/2018/40035

Research Article Open access CC BY 4.0

The Recyclable Bronsted Acidic Liquid Resin Mediated Eco-benign Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones and 3,4-Dihydropyrimidin-2(1H)-thiones via Biginelli Reaction

D. Parthiban, R. Joel Karunakaran, C. J. Magesh

International Research Journal of Pure and Applied Chemistry · pp. 1–10 · Published 7 Mar 2018

10.9734/IRJPAC/2018/40035

Abstract

Aim: To synthesis 3,4-Dihydropyrimidin-2(1H)-ones and 3,4-Dihydropyrimidin-2(1H)-thiones using phenol formaldehyde resin as a catalyst. Study Design: Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and 3,4-Dihydropyrimidin-2(1H)-thiones by cyclocondensation of ethyl or methyl acetoacetates, aldehydes and urea or thiourea using Bronsted acidic phenol-formaldehyde liquid resin as homogenous catalyst and as reaction medium under solvent-free condition. Methodology: Cyclocondensation of aromatic aldehyde, (thio) urea, ketoester was done in the presence of phenol-formaldehyde resin at 110°C with stirring for appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction. The product was extracted by ethyl acetate solvent. The product was purified either by recrystallization in hot ethanol or by column chromatography. All the products were thoroughly characterised by FT-IR, 1H-NMR, 13C-NMR, Mass spectral and CHN elemental analysis. Results: 15 different 3,4-Dihydropyrimidin-2(1H)-ones were synthesized and characterized thoroughly. Conclusion: We have developed an efficient method for one pot synthesis of 3,4-dihydropyrimidine-2-ones (DHPOs) and 3,4-dihydropyrimidine-2-thiones (DHPTs) by employing phenol-formaldehyde liquid resin as catalyst as well as medium for the Biginelli reaction. The advantages of this procedure includes not only free from volatile organic solvent, toxic metal catalyst, strong acid, but simple procedure, shorter reaction time, easy workup, and reusable catalysts conditions, and formation of pure products in good to excellent yields.

3,4-Dihydropyrimidin-2(1H)-ones 3,4-Dihydropyrimidin-2(1H)-thiones Biginelli reaction Phenol-formaldehyde resin Solvent free condition Multicomponent reactions

Cited by 10

Bi‐tailed N‐cationic surfactant promoted green synthesis of 2‐amino‐5‐oxo‐4‐alkyl‐4,5‐dihydropyrano[3,2‐c]chromene‐3‐carbonitrile derivatives via multicomponent reaction

Devendiran Parthiban · Journal of Heterocyclic Chemistry · 2023

Mangrove tree aerial root extract mediated green synthesis of Ag/Fe3O4/GO nanocomposite and its application as a catalyst for one pot synthesis of 7-phenyl-6H,7H-benzo[4,5]imidazo[2,1-b]chromeno[4,3-d][1,3]thiazin-6-one derivatives

Devendiran Parthiban, Muniyan Ramasamy Kuppusamy, Chinnaswamy Vanitha · 2024

Polymer Supported Ferric Chloride as Heterogeneous Catalyst for Three Component Biginelli Reaction

Akash V. Gujarati, Ashutosh V. Bedekar, Arun L. Patel · Catalysis Letters · 2024

1, 1’-Sulfinyldiethylammonium Bis (Hydrogen Sulfate) as a Recyclable Dicationic Ionic Liquid Catalyst for the Efficient Solvent-free Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones via Biginelli Reaction

Zainab Ehsani-Nasab, Ali Ezabadi · Combinatorial Chemistry & High Throughput Screening · 2020

Benzethonium Chloride Catalyzed one Pot Synthesis of 2,4,5-Trisubstituted Imidazoles and 1,2,4,5-Tetrasubstituted Imidazoles in Aqueous Ethanol As A Green Solvent

D. Parthiban, R. Joel Karunakaran · Oriental Journal of Chemistry · 2018

Choline Chloride: Zinc Chloride Ionic Liquid Mediated Inverse Electron Demand (IED) Diels-Alder Reaction; An eco-benign Synthesis of Pyranoquinolines and Furanoquinolines

Palani Amudha, Gnanamani Lavanya, Karuppan Venkatapathy · Letters in Organic Chemistry · 2019

A facile and green synthesis of methyl 7-aryl-5-methyl-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate derivatives using hyamine in aqueous media at room temperature

Peeli Kumar Anjali, Muniyan Ramasamy Kuppusamy, Devendiran Parthiban · Synthetic Communications · 2026

Plant-Based Bronsted Acidic Polyphenol Catalyzed Synthesis of 3'-Phenyl-1' H -Spiro[Cyclohexane-1,2'-Quinazolin]-4'(3' H )-Ones and 3'-Phenyl-1' H -Spiro[Cyclopentane-1,2'-Quinazolin]-4'(3' H )-One Derivatives

Devendiran Parthiban · Polycyclic Aromatic Compounds · 2022

A nanocrystalline CdS thin film as a heterogeneous, recyclable catalyst for effective synthesis of dihydropyrimidinones and a new class of carbazolyl dihydropyrimidinones via an improved Biginelli protocol

K. Venkatapathy, C. J. Magesh, G. Lavanya · New Journal of Chemistry · 2019

Mangrove tree aerial root extract mediated green synthesis of Ag/Fe3O4/rGO nanocomposite and its application as a catalyst for one pot synthesis of 7-phenyl-6H,7H-benzo[4,5]imidazo[2,1-b]chromeno[4,3-d][1,3]thiazin-6-one derivatives

Devendiran Parthiban, Muniyan Ramasamy Kuppusamy, Chinnaswamy Vanitha · Environmental Science and Pollution Research · 2024

Investigation of the H3PO4-Promoted Reaction of Benzaldehydes, Ethyl Acetoacetate or Ethyl Cyanoacetate or Malononitrile in the Presence of Urea as a Route to Pyrimidin-2-ones and 2-Iminochromenes — shares topic coverage
Eco-Friendly Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones Using Ionic Liquid [Msim]Cl as a Catalyst and Development of Novel Derivatives — shares topic coverage
Regioselectivity in the Multicomponent Reaction of 5-aminopyrazoles, Meldrum’s Acid and Triethyl Orthoformate — shares topic coverage

Access this article

View at publisher

Cite this article

D. Parthiban, R. Joel Karunakaran, C. J. Magesh (2018). The Recyclable Bronsted Acidic Liquid Resin Mediated Eco-benign Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones and 3,4-Dihydropyrimidin-2(1H)-thiones via Biginelli Reaction. International Research Journal of Pure and Applied Chemistry , 1–10. https://doi.org/10.9734/IRJPAC/2018/40035

Affiliations

D. Parthiban — P.G. and Research Department of Chemistry, Arignar Anna Govt. Arts College, Cheyyar, Tamilnadu 604407, India
R. Joel Karunakaran — Department of Chemistry, Madras Christian College, Tambaram, Tamilnadu 600059, India
C. J. Magesh — P.G. and Research Department of Chemistry, Arignar Anna Govt. Arts College, Cheyyar, Tamilnadu 604407, India

Metrics

0
Views: 0
Downloads: 10
Citations: 0
Outbound

Full metrics

Article metrics

Real usage data collected on this platform.

0

Page views

0

PDF downloads

0

Outbound clicks

10

Citations

Views by country

Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".

No views recorded yet.

Traffic sources

Referring site, by host.

No traffic recorded yet.

Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.