Development of a Practical Synthesis of a Pyrimidine Derivative with Fungicidal Activity

Ryan, Sarah J.

doi:10.1021/acs.oprd.9b00130

Cited by 11 publications

(2 citation statements)

References 20 publications

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“…The adduct 12 of phenyl(pyrimidin-2-yl)methanone could be isolated in moderate results (76% yield with 73% ee) with the use of the five-carbon-linked ligand L 5 -RaPr 2 . In addition, pyridine–pyrimidine-based alcohols 13 and 14 , analogues to a fungicide lead, , could be obtained in moderate-to-good enantioselectivity. Moreover, with the use of the ligand L 4 -RaPr 2 , pyridin-2-yl(quinolin-2-yl)methanone could afford the corresponding product 15 with moderate yield (64% yield) and high enantioselectivity (90% ee).…”

Section: Resultsmentioning

confidence: 99%

Visible-Light-Activated Asymmetric Addition of Hydrocarbons to Pyridine-Based Ketones

et al. 2022

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Enantioselective photoreduction of ketones with hydrocarbons is promising for the straightforward construction of chiral tertiary alcohols. But it is generally promoted by ultraviolet light via ketyl radical–alkyl radical coupling, which suffers from a competitive charge-transfer process and self/cross radical coupling reactions. An appropriate selection of a chiral catalyst that can alter the reaction pathway and deliver spatial selection is required. Accordingly, we disclosed a combined system involving Er(III)-based chiral Lewis acid catalysis, Ir(III)-based photoredox catalysis, and bromide-radical-mediated hydrogen atom transfer. The introduction of a bulky and nonredox chiral Lewis acid through the photoredox pathway enables the radical addition process and inhibits the above competitive reactions. The visible-light-promoted catalytic asymmetric alkylation of heteroaryl-based ketones with diverse hydrocarbons (mainly benzyl) delivered a variety of congested enantioenriched tertiary alcohols (up to 97% yield, 96% enantiomeric excess (ee)).

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Section: Resultsmentioning

confidence: 99%

Visible-Light-Activated Asymmetric Addition of Hydrocarbons to Pyridine-Based Ketones

et al. 2022

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“…Pyrimidines and fused pyrimidines are heterocyclic aromatic compounds with a particular interest because they represent a large class of natural and synthetic compounds; many of which have biological and therapeutic applications [1,2]. Pyrimidine and fused pyrimidines are significant in agriculture chemicals; insecticides [3,4], rodenticide [5,6], fungicides [7,8], and herbicides [9,10]. Pharmaceutical's preparations are some of the biological activities of fused pyrimidines derivatives [11,12], e.g., anticancer [13,14], antimicrobial agents [15,16] and antibacterial [17].…”

Section: Introductionmentioning

confidence: 99%

Biological Activity of Fused Pyrimidine Derivatives on Vital Parameters of Male Albino Rats

Mahmoud

2022

Bulletin of Faculty of Science, Zagazig University

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The objective of the current study was to evaluate the toxicity of oral administration of three synthesized organic compounds by us; 2-Amino-3-benzyl-6-(benzylthio) pyrimidin-4(3H)-one (amino pyrimidine), 3-Benzyl-7-hydroxy-5-(4-hydroxyphenyl)-2-(phenylamino)pyrido [2,3-d]pyrimidin-4(3H)-one (pyridopyrimidine) and N -{[1-Benzyl-4-(benzylthio)-6-oxo-1,6-dihydropyrimidin-2yl]carbamothioyl}benzamide (pyrimidine benzamide) for 28 days on some biochemical parameters and hepatic and renal histopathological changes in male albino rats. All the three tested pyrimidine's derivatives showed significant decrease of the body weight, total proteins and significant increase in liver weight and liver index when compared to control group. Additionally, the activities of serum transaminases (ALT and AST) and alkaline phosphate (ALP) were increased significantly in amino pyrimidine, pyridopyrimidine and pyrimidine benzamide treated groups when compared to control group. Moreover, significant inhibition of serum cholinesterase activity (ChE) and hemoglobin (Hb) value were observed with oral administration of the three investigated pyrimidine's derivatives in comparison to control rats. Concerning renal function indicators; serum urea was increased significantly in rats after receiving amino pyrimidine, pyridopyrimidine and pyrimidine benzamide. On the other hand, creatinine levels were increased by administration of amino pyrimidine, pyridopyrimidine and pyrimidine benzamide.The MDA level was detected to be increased significantly and TAC was decreased significantly in rats received amino pyrimidine, pyridopyrimidine, and pyrimidine benzamide. Histopathological examination of rats administered amino pyrimidine, pyridopyrimidine and pyrimidine benzamide, revealed disturbed hepatic and renal architecture that confirm the biochemical results which report hepatic and renal damage. The obtained data demonstrate the toxic effect of the evaluated fused pyrimidine derivatives in male albino rats.

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Reactivity of 4‐pyrimidyl Sulfonic Esters in Suzuki‐Miyaura Cross‐Coupling Reactions in Water Under Microwave Irradiation

et al. 2021

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The reactivity of four 4‐pyrimidyl sulfonic esters in Palladium‐catalyzed Suzuki–Miyaura cross‐coupling reactions was studied with various boronic acids. All the reactions were conducted in water under microwave irradiation. Electron‐rich aryl boronic acids exhibited higher yields when triflate (−OSO2CF3) was used as the pseudohalide, whereas electron‐poor aryl boronic acids reacted faster when nonaflate was employed (−OSO2(CF2)3CF3). Furthermore, the reactivity guide for Pd‐catalyzed coupling of these accessible pseudohalides with boron‐based coupling partners was applied to synthesize a bipyrimidine in excellent yield. Finally, the 2‐methylpyrimidines obtained are suitable starting materials for the synthesis of luminescent sensors.

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Development of a Practical Synthesis of a Pyrimidine Derivative with Fungicidal Activity

Cited by 11 publications

References 20 publications

Visible-Light-Activated Asymmetric Addition of Hydrocarbons to Pyridine-Based Ketones

Visible-Light-Activated Asymmetric Addition of Hydrocarbons to Pyridine-Based Ketones

Biological Activity of Fused Pyrimidine Derivatives on Vital Parameters of Male Albino Rats

Reactivity of 4‐pyrimidyl Sulfonic Esters in Suzuki‐Miyaura Cross‐Coupling Reactions in Water Under Microwave Irradiation

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