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An organocatalyst bound alpha-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions

A catalyst bound alpha-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N301 – PubChem

More research is needed about Phthalazine

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Metal-Free Oxidative Decarbonylative Coupling of Aliphatic Aldehydes with Azaarenes: Successful Minisci-Type Alkylation of Various Heterocycles

A metal-free oxidative decarbonylative coupling of aliphatic aldehydes with various electron-deficient heterocycles has been developed. This reaction is supposed to be realized via a Minisci-type mechanism, based on the substrate scope, regioselectivity and radical trapping experiments. The ready availability of aliphatic aldehydes, metal-free conditions and broad substrate scope should make this method attractive for the late-stage alkylation of bioactive heterocycles.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N435 – PubChem

Brief introduction of Phthalazine

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Facile synthesis, characterization, and antimicrobial evaluation of novel heterocycles, Schiff bases, and N-nucleosides bearing phthalazine moiety

The present work describes convenient synthesis of the novel Schiff bases 5a and b by reacting phthalazinones 4a and b with 4-methoxybenzaldehyde Reaction of the Schiff bases with phenylisothiocyanate afforded diazetidine derivatives 7a and b. Also, compounds 4a and b reacted with 2-bromoglucoside tetraacetate giving peracetylated N-glycosides 6a and b, which were deacetylated to afford N-glycosylated phthalazinones 8a and b. On the other hand, when compound 3 was treated with POCl3/PCl5 and/or ethyl chloroacetate, chlorophthalazine and ethyl acetate derivatives 9 and 10 were obtained, respectively. Hydrazinolysis of compounds 9 and 10 produced the hydrazino and hydrazide derivatives 11 and 12, respectively. When compound 11 reacted with 2-furanaldehyde, acetic anhydride, and/or carbon disulphide, it gave compounds 13-15, respectively. Treatment of the hydrazide 12 with aromatic aldehydes, acetic anhydride, ethyl acetoacetate, acetyl acetone, ammonium thiocyanate, and/or phthalic anhydride furnished compounds 17-21. Meanwhile, reacting Schiff base 22 with the chlorophthalazine derivative 9 produced compound 23, which on treatment with furoyl chloride produced compound 24. The structures of the novel compounds were confirmed by IR, 1H-NMR, 13C-NMR, MS, and elemental analysis. The newly synthesized compounds were tested against Bacillus subtilis and Staphylococcus aureus as Gram-positive bacteria, Escherichia coli and Pseudomonas aurignosa as Gram-negative bacteria, and Candida albicans and Aspergillus Niger as fungi strains. Compounds 5a and b, 23, and 24 showed greater antimicrobial activity than the stranded compounds, suggesting that they could be considered as promising antimicrobial agents.

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Phthalazine | C8H6N48 – PubChem

Properties and Exciting Facts About Phthalazine

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Copper-Catalyzed multicomponent coupling of organoindium reagents with nitrogen-Containing aromatic heterocycles

A mild, copper-catalyzed coupling of organoindium reagents with nitrogen-containing aromatic heterocycles and chloroformates is described. This reaction proceeds with a range of organoindium reagents, yielding predominately or exclusively the 1,4-addition products with pyridine. In addition, a range of other nitrogen-containing heterocycles can be employed in this reaction (e.g. benzoxazole, benzothiazole, phthalazine). As an illustration of the utility of this reaction, this heterocycle functionalization is coupled with a subsequent oxidation to achieve the one-pot synthesis of functionalized pyridine and benzothiazole derivatives.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N75 – PubChem

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A modular synthesis of polysubstituted indolizines

The N-alkylation of pyridines with cyanohydrin triflates or alpha-halonitriles furnishes 1-(1-cyanoalkyl)pyridinium salts that can react with nitroolefins under basic conditions to furnish polysubstituted indolizines. Overall, the indolizine core can be constructed from a pyridine, two aldehydes, and a nitroalkane, and no undesired functional groups remain in the products. When bromoacetonitrile was used for the N-alkylation, indolizine-3-carbonitriles were obtained instead. The pyridine component may be replaced by other azines, giving rise to related heterocyclic systems. Polysubstituted indolizines were synthesized through [3+2] cycloaddition of nitroalkenes with pyridinium ylides. In contrast to previous reports of 1,3-dipolar cycloadditions, in this work no electron-deficient groups remain in the products. Copyright

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Phthalazine – Wikipedia,
Phthalazine | C8H6N242 – PubChem

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Identification of enzymes responsible for dantrolene metabolism in the human liver: A clue to uncover the cause of liver injury

Dantrolene is used for malignant hyperthermia during anesthesia, and it sometimes causes severe liver injury as a side effect. Dantrolene is metabolized to acetylaminodantrolene, which is formed via the reduction of dantrolene to aminodantrolene and subsequent acetylation. Formation of hydroxylamine during the metabolic process may be associated with liver injury. We identified the enzymes responsible for dantrolene metabolism in humans to elucidate the mechanism of liver injury. Dantrolene reductase activity was not detected in human liver microsomes, but it was detected in cytosol. Formation was increased in the presence of N1-methylnicotineamide, which is an electron donor to aldehyde oxidase 1 (AOX1). Potent inhibitors of AOX1 and a correlation study with a marker of AOX1 activity, namely phthalazine oxidase activity, in a panel of 28 human liver cytosol samples supported the role of AOX1 in dantrolene reduction. Acetylaminodantrolene formation from aminodantrolene was highly detected in recombinant N-acetyltransferase (NAT) 2 rather than NAT1. A glutathione trapping assay revealed the formation of hydroxylamine via an AOX1-dependent reduction of dantrolene but not via hydroxylation of aminodantrolene. In conclusion, we found that AOX1 and NAT2 were responsible for dantrolene metabolism in humans and that AOX1-dependent metabolism determines dantrolene-induced liver injury.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N37 – PubChem

Archives for Chemistry Experiments of Phthalazine

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Copper(I) thiocyanate networks with aromatic diimine ligands

A total of five new CuSCN-LL complexes with aromatic diimine ligands, LL = quinoxaline (Qox), quinazoline (Qnz), phthalazine (Ptz), 2-aminopyrazine (2-NH2Pyz), and 2-methoxypyrazine (2-MeOPyz) have been prepared and characterized by crystallographic methods. The following compounds are reported: (CuSCN)2(Qox) (1), (CuSCN)(Qnz) (2), (CuSCN)2(Ptz) (3), (CuSCN)2(2-NH2Pyz) (4), and (CuSCN)(2-MeOPyz) (5). Compounds 1-4 were prepared using an extended aqueous reflux method in the presence of KSCN and ammonia. Compound 5 was prepared by directly reacting solid CuSCN with the liquid ligand. In complexes 2 and 5, LL is monodentate, while in others LL is bridging bidentate. All network structures are 2-D sheets, consisting of mu2-LL-crosslinked CuSCN ladders for 1 and 4, LL-decorated CuSCN sheets for 2 and 5, and unusual mu2-LL-“stapled” sheets for 3.

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Phthalazine | C8H6N46 – PubChem

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NMR spectra of nitrogen-containing compounds. Correlations between experimental and GIAO calculated data

Correlations between experimentally determined chemical shifts (15N, 13C, 1H in CDCl3 and DMSO solutions) and GIAO-calculated isotropic shielding constants, deltaexpt = a + bsigmacalcd, are reported that were obtained from a series of nitrogen-containing heterocycles (5-, 6-, 5 + 6-, 6 + 6- and 6 + 6 + 6-membered rings). Based on HF, MP2 and B3LYP optimized geometries [6-31G(d,p) basis set], GIAO calculations were performed at the HF, BLYP, and B3LYP levels of theory [6-311 + +G(d,p) basis set]. The performance of theoretical NMR calculations and the resulting eligibility for routine practical use were assessed from correlation coefficients and from standard deviations of the theoretically predicted shifts. Depending on the experimental conditions and on computational levels, linear regressions between experimental and theoretical data resulted in standard deviations of about 6-12 ppm for all nitrogens, 5-8 ppm for aromatic nitrogens, 1-2 ppm for aromatic carbons and 0.1-0.15 ppm for aromatic hydrogens. Several points that influence the accuracy of theoretically predicted chemical shifts are discussed. Copyright

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Stacks and clips: Uncanny similarities in the modes of self-assembly in ternary Ag(i) complexes with 1,2-diazines and chelating heteroarenes

The first syntheses and structural elucidation of Ag(i) ternary complexes with 1,2-diazines and chelating heteroarenes have been described. Conserved modes of inter-cation Ag+…pi and pi…pi stacking interactions result in near identical patterns of cation self-assembly in these ternary complexes. The Royal Society of Chemistry 2013.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N452 – PubChem

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Synthesis, biological screening of novel long chain derivatives of 1,3-disubstituted-1H-pyrazol-5(4H)-one and 2-substituted-3H-1,4-phthalazin-1,4-dione: Structure-activity relationship studies

The main purpose of this study is to synthesize novel heterocyclic derivatives of fatty acids which are also biologically important. The simple, efficient and one-pot synthesis of two novel series of 1-long chain alkanoyl/alkenoyl/hydroxyalkenoyl-3-methyl-1H-pyrazol-5(4H)-ones 2(a-e) and 2-long chain alkenoyl/hydroxyalkenoyl-3H-phthalazin-1,4-diones 3(b-e) is achieved by the reaction of ethylacetoacetate/phthalic anhydride and long chain alkyl/alkenyl/hydroxyalkenyl hydrazides 1(a-e). Although some methods are available for the synthesis of phthalazindiones and pyrazolones, the development of a new synthetic method for the efficacious build up of heterocycles (phthalazindiones and pyrazolones) substituted with long alkanoyl/alkenoyl/hydroxyalkenoyl chain is an interesting challenge in the field of synthesis of novel compounds of fatty acids that includes heterocyclization and derivatization of fatty acids. Compounds 2(a-e) were synthesized by the cyclization reaction between ethylacetoacetate and long alkyl/alkenyl/hydroxyalkenyl chain hydrazides 1(a-e). Compounds 3(b-e) were synthesized by the reaction of phthalic anhydride and long alkenyl/hydroxyalkenyl chain hydrazides 1(b-e) in absolute ethanol/glacial AcOH. Structures of all the newly synthesized compounds have been elucidated by means of IR, 1H NMR, 13C NMR and MS. Newly synthesized compounds were evaluated for in vitro antibacterial and antifungal activities and their structure-activity relationship studies have been carried out.

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