301359-47-7

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 
• 17356-08-0 thiourea 

Downstream Products

• 1448553-02-3 C₂₃H₂₁FN₂O₂S 
• 1448553-01-2 C₂₃H₂₃FN₂O₃S 

Relevant academic research and scientific papers

Phthalic acid: A green, biodegradable and environmentally benign nature difunctional Br?nsted acid catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and substituted dihydro-2-oxypyrroles

Phthalic acid as a green, biodegradable economical and environmentally benign nature catalyst for the one-pot three-component Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives via β-keto esters, aldehyde derivatives and urea/thiourea under thermal and solvent-free conditions and one-pot four-component domino condensation of substituted dihydro-2-oxypyrrole by reaction of dialkyl acetylenedicarboxylate, formaldehyde and amines (aromatic and aliphatic) under ambient temperature with short reaction times and excellent yields is reported. The most benefits this procedure are such as green, biodegradable, inexpensive and non-toxic catalyst, eco-friendly, high catalytic activity, efficient, easily separation with no column chromatographic separation, simple operational procedures, one-pot, excellent yields, environmentally benign nature.

In silico design and synthesis of tetrahydropyrimidinones and tetrahydropyrimidinethiones as potential thymidylate kinase inhibitors exerting anti-tb activity against Mycobacterium tuberculosis

Background and Purpose: Tuberculosis has been reported to be the worldwide leading cause of death resulting from a sole infectious agent. The emergence of multidrug-resistant tuberculosis and extensively drug-resistant tuberculosis has made the battle against the infection more difficult since most currently available therapeutic options are ineffective against these resistant strains. Therefore, novel molecules need to be developed to effectively treat tuberculosis disease. Preliminary docking studies revealed that tetrahydropyrimidinone derivatives have favorable interactions with the thymidylate kinase receptor. In the present investigation, we report the synthesis and the mycobacterial activity of several pyrimidinones and pyrimidinethiones as potential thymidylate kinase inhibitors. Methods: The title compounds (1a–d)and(2a–b) were synthesized by a one-pot three-component Biginelli reaction. They were subsequently characterized and used for whole-cell anti-TB screening against H37Rv and multidrug-resistant (MDR) strains of Mycobacterium tuberculosis (MTB) by the resazurin microplate assay (REMA) plate method. Molecular modeling was conducted using the Accelry’s Discovery Studio 4.0 client program to explain the observed bioactivity of the compounds. The pharmacokinetic properties of the synthesized compounds were predicted and analyzed. Results: Of the compounds tested for anti-TB activity, pyrimidinone 1a and pyrimidinethione 2a displayed moderate activity against susceptible MTB H37Rv strains at 16 and 32 μg/mL, respectively. Only compound 2a was observed to exert modest activity at 128 μg/mL against MTB strains with cross-resistance to rifampicin and isoniazid. The presence of the trifluoro-methyl group was essential to retain the inhibitory activity of compounds 1a and 2a. Molecular modeling studies of these compounds against thymidylate kinase targets demonstrated a positive correlation between the bioactivity and structure of the compounds. The in-silico ADME (absorption, distribution, metabolism, and excretion) prediction indicated favorable pharmacokinetic and drug-like properties for most compounds. Conclusion: Pyrimidinone 1a and pyrimidinethione 2a were identified as the leading compounds and can serve as a starting point to develop novel anti-TB therapeutic agents.

Three-component reaction of β-keto esters, aromatic aldehydes and urea/thiourea promoted by caffeine, a green and natural, biodegradable catalyst for eco-safe Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones derivatives under solvent-free co

Caffeine was found to be a natural and green and biodegradable catalyst for the one-pot, three-component condensation Biginelli reaction of β-keto esters, aromatic aldehydes and urea/thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones/thi

Br?nsted acidic 1-ethyl-1,2,4-trizolium phenylsulfonate as catalyst for biginelli reaction

A Br?nsted acidic 1-ethyl-1,2,4-triazolium phenylsulfonate has been synthesized and characterized. A catalytic study is performed for 1-ethyl-1,2,4-triazolium phenylsulfonate as acid catalyst for a multicomponent reaction of synthesis of series of 3,4-dih

Clean and one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thione derivatives using maleic acid as an efficient and environmentally benign natural di-functional Br?nsted acid catalyst under solvent-free conditions

An efficient synthesis of Biginelli-type compounds using maleic acid as an economical di-functional Br?nsted acid catalyst in a one-pot, three-component reaction of β-ketoesters (methyl or ethyl acetoacetate), aromatic aldehyde (benzaldehye derivatives) a

Metal-Free Visible-Light-Mediated Desulfurization and Aromatization of Dihydropyrimidine-2-thiones for Synthesis of 2-Unsubstituted Pyrimidines

The visible-light-mediated aerobic desulfurization and aromatization of Biginelli 3,4-dihydropyrimidine-2(1H)-thiones for a one-step synthesis of 2-unsubstituted pyrimidines was established. The protocol uses molecular oxygen as an inexpensive oxidant, wi

A unique opportunity for the utilization of glass wastes as a resource for catalytic applications: toward a cleaner environment

Although glass recycling has been conducted since 1970s, and even though recycled glass waste has been used in the construction of various alternative products, the utilization of glass waste for catalytic applications has not been fully considered until

Saccharin: a green, economical and efficient catalyst for the one-pot, multi-component synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and 1H-pyrazolo [1,2-b] phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole

Abstract: In this method, we have reported the catalytic ability of saccharin as a green, eco-friendly catalyst for the multi-component efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives and 1H-pyrazolo [1,2-b]phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole with excellent yields and short reaction times. This present methodology has notable benefits such as green, inexpensive and non-toxic catalyst, one-pot, environmental benign nature, solvent-free conditions, simplicity of operation with no necessity of chromatographic purification steps and eco-friendly. Graphical Abstract: We have studied the catalytic ability of saccharin as a green, economical and environmentally benign nature for the multi-component efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones derivatives, 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and substituted dihydro-2-oxypyrrole with excellent yields and short reaction times. Green catalyst, mild, non-toxic, inexpensive, simple operational procedures, one-pot, high catalytic activity, eco-friendly, easily separated from the reaction mixture with no column chromatographic for the one-pot multi-component synthesis of these compounds are the most important advantages of this procedure.[Figure not available: see fulltext.]

Synthesis of 1-alkyl triazolium triflate room temperature ionic liquids and their catalytic studies in multi-component Biginelli reaction

Synthesis of three Brnsted acid-based ionic liquids, namely, 1-ethyl-1,2,4-triazolium triflate (1a), 1-propyl-1,2,4-triazolium triflate (1b) and 1-butyl-1,2,4-triazolium triflate (1c), is described. These ionic liquids have been employed as catalysts for

Hydrophobicity-enhanced magnetic solid sulfonic acid: A simple approach to improve the mass transfer of reaction partners on the surface of the heterogeneous catalyst in water-generating reactions

Two novel and environmentally benign organosulfonic acid-functionalized silica-coated magnetic nanoparticle catalysts 1 (Fe3O 4@SiO2@Et-PhSO3H) and 2 (Fe3O 4@SiO2@Me&Et-PhSO3H) were prepared and their surface hydrophobicity was assessed by esterification reaction of fatty alcohols. Also, their water-toleration in two water-generating reactions was investigated, namely: synthesis of bis(indolyl)methane and the Biginelli reaction of benzaldehyde, methyl acetoacetate, and urea under solvent-free conditions. In these reactions, the catalyst 2 that was more hydrophobic and water-resistant showed higher catalytic activity and was characterized extensively by various techniques. This catalyst was successfully used in the Biginelli reaction of a series of aldehydes, β-keto esters, and urea/thiourea for the synthesis of a diverse range of pharmacologically active 3,4-dihydropyrimidin-2-one/thione (DHPM) derivatives. The catalyst 2 was easily separated by an external magnet and the recovered catalyst was reused in five cycles without any significant loss of activity.