scholarly journals A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation

2020 ◽  
Vol 11 (3) ◽  
pp. 179-186
Author(s):  
Shunan Kaping ◽  
Philippe Helissey ◽  
Jai Narain Vishwakarma
Keyword(s):  
Aqueous Media ◽  
Ultrasound Irradiation ◽  
Mass Spectral Data ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Triclinic Space Group ◽  
X Ray ◽  
Mass Spectral ◽  
Chemical Structures ◽  
Crystallographic Study

A simple and efficient synthesis of substituted pyrazolo[1,5-a]pyrimidine derivatives has been developed by the use of ultrasound. 5-Methyl-4-phenyl-1H-pyrazol-3-amine required for the synthesis of pyrazolo[1,5-a]pyrimidine derivatives has been easily obtained by the reaction of 3-(dimethylamino)-2-phenylacrylonitrile (formed from readily available 2-phenylacetonitrile) with hydrazine hydrate in refluxing ethanol. The 5-aminopyrazole was then reacted with various formylated active proton compounds in presence of KHSO4 in aqueous medium under ultrasound irradiation to give the desired products. The chemical structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. X-ray crystallographic study of a selected compound 6-(4-chlorophenyl)-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine (7c) was performed to ascertain the regioselectivity of the reaction. Crystal data for compound 7c: Triclinic, space group P-1 (no. 2), a = 8.0198(3) Å, b = 14.0341(6) Å, c = 14.2099(6) Å, α = 87.672(2)°, β = 83.902(2)°, γ = 89.120(2)°, V = 1588.87(11) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.248 mm-1, Dcalc = 1.400 g/cm3, 12918 reflections measured (4.012° ≤ 2Θ ≤ 49°), 5152 unique (Rint = 0.0411, Rsigma = 0.0429) which were used in all calculations. The final R1 was 0.0486 (I > 2σ(I)) and wR2 was 0.1320 (all data).

scholarly journals Ultrasound assisted synthesis of pyrazolo[1,5-a]pyrimidine-antipyrine hybrids and their anti-inflammatory and anti-cancer activities

2020 ◽  
Vol 11 (1) ◽  
pp. 68-79 ◽  
Author(s):  
Shunan Kaping ◽  
Melboureen Sunn ◽  
Laishram Indira Singha ◽  
Jai Narain Vishwakarma
Keyword(s):  
Biological Activities ◽  
Aqueous Media ◽  
Analytical Data ◽  
Ultrasound Irradiation ◽  
The Novel ◽  
Crystal Data ◽  
Triclinic Space Group ◽  
X Ray ◽  
Anti Cancer ◽  
Ultrasound Assisted

A series of antipyrinyl-pyrazolo[1,5-a]pyrimidines have been synthesized by reactions of aminopyrazole (4) with various formylated active proton compounds in the presence of KHSO4 (aqueous media), under ultrasound irradiation. The structures of the compounds have been established with the help of spectral and analytical data. N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide (6a) was further subjected to X-ray crystallographic studies to avoid any ambiguity of the derived structures. Crystal data for compound 6a, C51H46N12O5 (M =907.00 g/mol): triclinic, space group P-1 (no. 2), a = 9.9554(3) Å, b = 14.0875(4) Å, c = 17.4572(4) Å, α = 79.676(2)°, β = 85.283(2)°, γ = 72.647(2)°, V = 2297.97(11) Å3, Z = 2, T = 296.15 K, μ(MoKα) = 0.088 mm-1, Dcalc = 1.311 g/cm3, 29732 reflections measured (4.174° ≤ 2Θ ≤ 57.068°), 10681 unique (Rint = 0.0400, Rsigma = 0.0533) which were used in all calculations. The final R1 was 0.0566 (I > 2σ(I)) and wR2 was 0.1663 (all data). The novel compounds were also screened for their biological activities.

A greener procedure for the synthesis of α-ureidophosphonates under ultrasound irradiation. An X-ray crystallographic study

RSC Advances ◽  
2015 ◽  
Vol 5 (121) ◽  
pp. 99775-99780 ◽  
Author(s):  
Abdeslem Bouzina ◽  
Malika Berredjem ◽  
Sofiane Bouacida ◽  
Hocine Merazig ◽  
Nour-eddine Aouf
Keyword(s):  
Ultrasonic Irradiation ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
One Pot ◽  
X Ray ◽  
Catalyst Free ◽  
Crystallographic Study ◽  
Three Component Reaction

The synthesis of α-ureidophosphonates via a one-pot three-component reaction using ultrasonic irradiation under solvent- and catalyst-free conditions at 75° is developed. The products were obtained in excellent yields within short reaction times.

scholarly journals One-pot synthesis of new Pyrido [2,3-d] Pyrimidine derivatives under ultrasonic irradiation using organo catalyst 4-Dimethylaminopyridine (DMAP)

2016 ◽  
Vol 3 (1) ◽  
Author(s):  
Imtiyaz Rasool Parrey ◽  
Athar Adil Hashmi
Keyword(s):  
Ultrasonic Irradiation ◽  
Aromatic Aldehydes ◽  
Major Effect ◽  
Mass Spectral Data ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Environment Friendly ◽  
Mass Spectral ◽  
One Pot Synthesis ◽  
The One

AbstractThe one-pot synthesis of pyrido[2,3-d] pyrimidine derivatives has been reported via Knoevenagel-Michal addition pathways using substituted aromatic aldehydes, Cyanoacetamide and 6-aminouracil in N,N-dimethylformamide (DMF) solvent, with 4-dimethylaminopyridine (DMAP) as new organo catalyst catalyst under ultrasonic irradiation. The results showed that a series of aromatic aldehydes were effectively used to prepare the targeted pyrido [2, 3-d] pyrimidine derivatives with good to excellent yields (81-93 %) with no major effect on the yield of product by electron donating/withdrawing substituents. Short reaction time, environment friendly procedure, excellent yields, inexpensive and readily available catalyst are the advantages of this procedure. All synthesized compounds were characterized by IR, 1HNMR, 13CNMR and mass spectral data.

An expeditious one-pot synthesis of pyrido[2,3-d]pyrimidines using Fe3O4–ZnO–NH2–PW12O40 nanocatalyst

2019 ◽  
Vol 43 (3-4) ◽  
pp. 135-139
Author(s):  
Pegah Farokhian ◽  
Manouchehr Mamaghani ◽  
Nosrat Ollah Mahmoodi ◽  
Khalil Tabatabaeian ◽  
Abdollah Fallah Shojaie
Keyword(s):  
Electron Microscopy ◽  
Vibrating Sample Magnetometer ◽  
X Ray Diffraction ◽  
Facile Synthesis ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
X Ray ◽  
Transmission Electron ◽  
Novel Method ◽  
Operational Simplicity

An efficient protocol for the facile synthesis of a series of pyrido[2,3- d]pyrimidine derivatives has been developed applying Fe3O4–ZnO–NH2–PW12O40 nanocatalyst in water. This novel method has the benefits of operational simplicity, green aspects by avoiding toxic solvents and high to excellent yields of products. Fe3O4–ZnO–NH2–PW12O40 was synthesized and characterized by Fourier transform infrared, X-ray diffraction, vibrating sample magnetometer, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and transmission electron microscopy analyses. The nanocatalyst is readily isolated and recovered from the reaction mixture by an external magnet.

scholarly journals Chemical Constituents of Phoebe poilanei and Their Cytotoxic Activity

2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1985096
Author(s):  
Nguyen Thi Viet Thanh ◽  
Tran Thi Minh ◽  
Dinh Thi Thu Hien ◽  
Ho Duc Cuong ◽  
Yohan Seo ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
High Resolution ◽  
Cytotoxic Activity ◽  
Spectral Data ◽  
Chemical Constituents ◽  
Flavonol Glycosides ◽  
Ionization Mass ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Chemical Structures

Two new flavonol glycosides, rhamnocitrin 3- O-α-L-rhamnopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (1) and quercetin 3- O-6- Z- p-coumaroyl-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranoside (2), along with 3 flavonol glycosides, isoquercitrin (3), rutin (4), and quercetin 3- O-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside (5), and two known sesquiterpenes, alismol (6) and spathulenol (7), were isolated from the leaves of Phoebe poilanei Kosterm. Their chemical structures were elucidated by analyses of their high-resolution electrospray ionization mass spectral data and nuclear magnetic resonance spectral data and comparison with those reported in the literature. Two sesquiterpenes 6 and 7 were found to exhibit moderate cytotoxic activity with IC50 values ranging from 21.6 to 29.8 µM.

scholarly journals Ferrocene-Containing Ionic Liquid Supported on Silica Nanospheres (SiO2@Imid-Cl@Fc) as a Mild and Efficient Heterogeneous Catalyst for the Synthesis of Pyrano[3,2-b]Pyran Derivatives Under Ultrasound Irradiation

2018 ◽  
Vol 42 (1) ◽  
pp. 7-12 ◽  
Author(s):  
Reza Teimuri-Mofrad ◽  
Somayeh Esmati ◽  
Masoumeh Rabiei ◽  
Mahdi Gholamhosseini-Nazari
Keyword(s):  
Ionic Liquid ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Ultrasound Irradiation ◽  
Xrd Analysis ◽  
Catalytic Performance ◽  
Significant Loss ◽  
One Pot ◽  
X Ray ◽  
Three Component Reaction

A novel heterogeneous silica nanosphere-supported ferrocene-containing ionic liquid catalyst (SiO2@Imid-Cl@Fc) was designed and synthesised and was systematically characterised by Fourier transform infrared (FTIR) spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) and X-ray diffraction (XRD) analysis. The catalytic activity of the SiO2@Imid-Cl@Fc catalyst was tested in a one-pot, three-component reaction of malononitrile and kojic acid with 15 aromatic aldehydes at room temperature under ultrasound irradiation. The products were pyrano[3,2-b]pyran derivatives, four of which are new. The catalyst exhibited good catalytic performance over short reaction times (15–20 min) and could be recycled at least five times without significant loss of activity.

scholarly journals FLAVONOIDS FROM FLOWERS OF AMESIODENDRON CHINENSE (SAPINDACEAE)

2020 ◽  
Vol 58 (6) ◽  
pp. 676
Author(s):  
Ho Van Ban ◽  
Trinh Thi Thanh Van ◽  
Vu Van Chien ◽  
Nguyen Thi Hue ◽  
Pham Thi Hang ◽  
...  
Keyword(s):  
Spectral Data ◽  
Physicochemical Parameters ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Chemical Structures

From the flowers of Amensiodendron Chinese (Merr.) Hu, six known flavonoids, (-)-catechin (1), (-)-epi-catechin (2), chrysoeriol (3), quercetin-3-O-β-D-glucopyranoside (4), astragalin (5) and kaempferide-3-O-β-D-glucopyranoside (6) were isolated. Their chemical structures were elucidated by analysis of the physicochemical parameters, the NMR and mass spectral data, and comparison with those reported in the literatures.

scholarly journals Microwave assisted synthesis and antimicrobial activity of some novel pyrimidine derivatives

2007 ◽  
Vol 72 (2) ◽  
pp. 109-117 ◽  
Author(s):  
S.J. Vaghasia ◽  
V.H. Shah
Keyword(s):  
Antimicrobial Activity ◽  
Antimicrobial Activities ◽  
Microwave Assisted Synthesis ◽  
Mass Spectral Data ◽  
Pyrimidine Derivatives ◽  
Plate Method ◽  
Mass Spectral ◽  
Microwave Assisted ◽  
New Compounds

The synthesis of thiazolo[5,4-d]pyrimidines can be achieved from different 5- thiazolidinones, 2-butyl-1H-imidazole-5-carbaldehyde and thiourea using microwave irradiation within 5 min. The structures of the products were supported by FTIR, PMR and mass spectral data. The in vitro antimicrobial activity of the synthesized thiazolo[5,4-d]pyrimidines 1a-j, having substituents at the 1- and 3-positions, were determined by the cup-plate method against several standard strains chosen to define the spectrum and potency of the new compounds. The antimicrobial activities of the thiazolo[5,4-d]pyrimidines 1a-j are compared with those of known chosen standard drugs, viz. ampicillin, chloramphenicol, ciprofloxacin, norfloxacin and griseofulvin. .

scholarly journals AN EFFICIENT THREE COMPONENT ONE-POT SYNTHESIS OF -1,2,3,4-TETRAHYDRO-4-OXO- 6-(5-SUBSTITUTED 2-PHENYL-1H-INDOL-3-YL)-2-THIOXOPYRIMIDINE-5-CARBONITRILE AS ANTIMICROBIAL AND ANTITUBERCULAR AGENTS

2021 ◽  
pp. 94-97
Author(s):  
PRABHAKER WALMIK
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Antitubercular Agents ◽  
Mass Spectral Data ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Spectral Techniques ◽  
Mass Spectral ◽  
One Pot Synthesis

Objective: The objective of the study was to synthesis of 1,2,3,4-tetrahydro-4-oxo-6-(5-substituted 2-phenyl-1H-indol-3-yl)-2-thioxopyrimidine-5- carbonitrile derivatives (4a-c). Methods: The structures of all these unknown compounds have been confirmed with the help of physical and spectral techniques such as IR, 1H, and 13C NMR and mass spectral data and these newly synthesized compounds were evaluated for in-vitro antimicrobial and antitubercular activities. Results: Screening studies have demonstrated that the newly synthesized compound 4a exhibited promising antimicrobial and antitubercular properties. Conclusion: The final results revealed that compound 4a exhibited promising antimicrobial and antitubercular properties when compared to the standard drugs.

ChemInform Abstract: A Greener Procedure for the Synthesis of α-Ureidophosphonates under Ultrasound Irradiation. An X-Ray Crystallographic Study.

ChemInform ◽  
2016 ◽  
Vol 47 (14) ◽  
Author(s):  
Abdeslem Bouzina ◽  
Malika Berredjem ◽  
Sofiane Bouacida ◽  
Hocine Merazig ◽  
Nour-eddine Aouf
Keyword(s):  
Ultrasound Irradiation ◽  
X Ray ◽  
Crystallographic Study
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