Day: December 21, 2022

Ma, Pengju published the artcilePhotocatalyst- and additive-free decarboxylative alkylation of N-aryl tetrahydroisoquinolines induced by visible light, Formula: C9H10O3, the main research area is alkyl aryl tetrahydroisoquinoline preparation; tetrachlorohydroxyphthalimide alkyl ester aryl tetrahydroisoquinoline decarboxylative alkylation.

Synthesis of C-1 alkylated tetrahydroisoquinoline products I (R = Pr, 4-oxocyclohexyl, oxan-4-yl, etc.; R1 = Ph, pyridin-4-yl, naphthalen-1-yl, etc.; R2 = H. MeO) and II via a visible light induced decarboxylative alkylation of N-aryl tetrahydroisoquinolines III (X = H) and 9-methyl-2-phenyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole has been developed using tetrachloro-N-hydroxyphthalimide esters IV as alkylation agents. This redox-neutral reaction can proceed without the assistance of photocatalysts, transition metals and external additives by irradiation with blue LEDs. Preliminary mechanistic studies indicated that this transformation probably proceeded through an electron donor-acceptor complex involved radical process.

Organic Chemistry Frontiers published new progress about Alkylation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Svec, Riley L. published the artcileImidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations, Safety of 4-Methoxyphenylacetic acid, the main research area is repurpose imidazotetrazine weighable diazomethane synthon esterification cyclopropanation; alkylation; cyclopropanation; diazo compounds; diazomethane; imidazotetrazines.

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chem. of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that Me ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a com. available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

Angewandte Chemie, International Edition published new progress about Alkylation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Safety of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Schiesser, Stefan published the artcileN-Trifluoromethyl Amines and Azoles: An Underexplored Functional Group in the Medicinal Chemist’s Toolbox, Formula: C8H11NO, the main research area is trifluoromethyl amine azole synthesis solubility permeability drug discovery.

Introducing trifluoromethyl groups is a common strategy to improve the properties of biol. active compounds However, N-trifluoromethyl moieties on amines and azoles are very rarely used. To evaluate their suitability in drug design, we synthesized a series of N-trifluoromethyl amines and azoles, determined their stability in aqueous media, and investigated their properties. We show that N-trifluoromethyl amines are prone to hydrolysis, whereas N-trifluoromethyl azoles have excellent aqueous stability. Compared to their N-Me analogs, N-trifluoromethyl azoles have a higher lipophilicity and can show increased metabolic stability and Caco-2 permeability. Furthermore, N-trifluoromethyl azoles can serve as bioisosteres of N-iso-Pr and N-tert-Bu azoles. Consequently, we suggest that N-trifluoromethyl azoles are valuable substructures to be considered in medicinal chem.

Journal of Medicinal Chemistry published new progress about Alkylation. 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Formula: C8H11NO.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Das, Kanu published the artcileN-Alkylation of Amines Catalyzed by a Ruthenium-Pincer Complex in the Presence of in situ Generated Sodium Alkoxide, Recommanded Product: 4-Methoxy-N-methylaniline, the main research area is secondary amine preparation density functional theory; alc primary amine alkylation ruthenium catalyst.

The use of ruthenium-NNN-pincer complexes of the type (R2NNN)RuCl2(PPh3) (R = tBu, iPr, Cy and Ph) for the catalytic N-alkylation of primary amines R-NH2 (R = Ph, propan-2-yl, thiophen-2-ylmethyl, etc.) under solvent-free conditions were reported. For the first time, the base that is required to promote these reactions is generated in situ from the alcs. R1-OH (R1 = Bu, (4-fluorophenyl)methyl, furan-2-ylmethyl, etc.) by the use of sodium. The resulting sodium alkoxide regenerates the alcs. substrate while acting as the water scavenger thus mitigating the need of an addnl. base. Among the catalysts screened, (tBu2NNN)RuCl2(PPh3) (0.02 mol-%) gives very high turnovers and good yields at 140 °C. The (tBu2NNN)RuCl2(PPh3) catalyzed N-alkylation tolerates a variety of amine and alc. substrates. While excellent turnover (29000) was obtained for the (tBu2NNN)RuCl2(PPh3) (0.002 mol-%) catalyzed alkylation of aniline with cyclohexyl methanol, the turnovers obtained in the corresponding catalytic methylation of p-anisidine was also very high (12000). The (tBu2NNN)RuCl2(PPh3) catalyzed reactions have also been accomplished under open-vessel conditions resulting in a net dehydrogenative coupling reaction. This protocol has been used to transform benzene-1,2-diamine to benzimidazoles I (R2 = H, F, OMe) with high productivity (12000 turnovers). DFT studies indicate that while β-hydride elimination is rate-determining (RDTS: 24.31 kcal/mol) for the alc. dehydrogenation segment which is endothermic, insertion of the imine is rate-determining (RDTS: 11.26 kcal/mol) for its hydrogenation that is exothermic.

European Journal of Organic Chemistry published new progress about Alkylation. 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Recommanded Product: 4-Methoxy-N-methylaniline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Kai published the artcileEnhanced Acidity and Activity of Aluminum/Gallium-Based Ionic Liquids Resulting from Dynamic Anionic Speciation, COA of Formula: C8H10O2, the main research area is acidity activity aluminum gallium based ionic liquid anionic speciation; Friedel Crafts acylation alkylation reaction catalyst.

To explore if the catalytic activity of single-metal species in halometallate catalysts can be enhanced with mixed-metal species, aluminum and gallium were simultaneously introduced to prepare a mixed-metal ionic liquid (IL) through a one-pot reaction of [HN222]Cl, AlCl3, and GaCl3 in various amounts The Lewis acidity in Friedel-Crafts acylation and alkylation reactions of these IL compositions were evaluated and all mixed-metal [HN222][xAlCl3 + (2 – x)GaCl3]Cl ILs exhibited higher catalytic activity than AlCl3, GaCl3, [HN222][Al2Cl7], or [HN222][Ga2Cl7]. The broadening in 27Al NMR of these ILs indicates the presence of dynamic anionic species, whereas matrix-assisted laser-desorption ionization time-of-flight (MALDI-TOF) and acetonitrile-probed Fourier transform IR (FT-IR) analyses correlates the structure-activity relationship, for instance, identifying the presence of mixed-metal-containing [Cl2GaOClAlClOGaCl2]- species in the better-performing ILs.

ACS Catalysis published new progress about Alkylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, COA of Formula: C8H10O2.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Navale, Balu S. published the artcilePropargyl α-aryl-α-diazoacetates as robust reagents for the effective C-H bond functionalization of 1,3-diketones via scandium catalysis, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is propargyl aryl dicarbonyl compound preparation; diketone propargyl aryl diazoacetate alkylation scandium catalyst.

Propargyl α-aryl-α-diazoacetates RC(=N2)C(O)OCH2CCH [R = 4-ClC6H4, naphthalen-2-yl, 3,4-(H3CO)2C6H3, etc.] a new class of reagents is developed for the effective C-H bond functionalization of 1,3-diketones R1C(O)CH2C(O)R1 (R1 = Me, Et, Ph, 4-H3CC6H4, 4-H3COC6H4) at room temperature The combination of scandium triflate and propargyl α-aryl-α-diazoacetates proved to be efficient catalyst-reagent system for the controlled C-H bond functionalization to afford 1,3-dicarbonyl alkylation products RCH(CH(C(O)R1)2)C(O)OCH2CCH. The protocol uses inexpensive Sc(OTf)3 (5 mol%) and the reaction did not require the use of expensive catalysts or ligands and worked efficiently at room temperature The practicality of the protocol has been demonstrated by the gram scale synthesis.

Tetrahedron Letters published new progress about Alkylation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Recommanded Product: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Denis, Camille published the artcileSynthesis of 3,3-Diarylazetidines by Calcium(II)-Catalyzed Friedel-Crafts Reaction of Azetidinols with Unexpected Cbz Enhanced Reactivity, SDS of cas: 151-10-0, the main research area is diarylazetidines preparation calcium catalyzed Friedel Crafts reaction; alkylation Cbz azetidine phenol intermediate carbocation.

Azetidines are valuable motifs that readily access under explored chem. space for drug discovery. 3,3-Diarylazetidines are prepared in high yield from N-Cbz azetidinols in a calcium(II)-catalyzed Friedel-Crafts alkylation of (hetero)aromatics and phenols, including complex phenols such as β-estradiol. Electron poor phenols undergo O-alkylation. The product azetidines can be derivatized to drug-like compounds through the azetidine nitrogen and the aromatic groups. The N-Cbz group is crucial to reactivity by providing stabilization of an intermediate carbocation on the four-membered ring.

Organic Letters published new progress about Alkylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, SDS of cas: 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Jiacheng published the artcileMinisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light, Application In Synthesis of 104-01-8, the main research area is alkylated quinoline preparation; quinoline acyloxy phthalimide ester Minisci type alkylation HE mediated; isoquinoline alkylated preparation; acyloxy phthalimide ester isoquinoline Minisci type alkylation HE mediated; pyridine alkylated preparation; phthalimide ester acyloxy pyridine Minisci type alkylation HE mediated.

A synthetic method that enabled the Hantzsch ester (HE)-mediated Minisci-type C2-alkylation of quinolines, isoquinolines and pyridines by N-(acyloxy)phthalimide esters (NHPI) to afford alkylated N-heterocyclic products, e.g., I, under blue LED (light emitting diode) light (456 nm) was described. Achieved under mild reaction conditions at room temperature, the metal-free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N-heterocyclic products in yields of 21-99%. On introducing a chiral phosphoric acid, an asym. version of the reaction was also realized and provided product enantiomeric excess (ee) values of 53-99%.

Advanced Synthesis & Catalysis published new progress about Alkylation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application In Synthesis of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Dong, Zheng-Yu published the artcileThe application of UV-C laser in persulfate activation for micropollutant removal: Case study with iodinated X-ray contrast medias, Recommanded Product: Diatrizoic Acid, the main research area is UV laser micropollutant removal iodinated X ray contrast media; Electron shuttle; Hydroxyl radical; Iodinated X-ray contrast media; Sulfate radical; UV-C laser.

A novel light source UV-C laser was applied in persulfate (PS) activation to effectively remove iodinated X-ray contrast medias (ICMs) including iohexol (IOX), iopamidol (IPM) and diatrizoate (DTZ) in this study. Significant ICMs degradation was observed in UV-C laser/PS systems with pseudo first-order rate constants of 0.022-0.067 s-1. Sulfate radicals (SO·-4) were the main active species in the three ICMs degradation, and the steady-state concentrations ([SO·-4]ss) were 3.629 x 10-11 M (IOX), 1.702 x 10-11 M (IPM) and 1.148 x 10-11 M (DTZ), resp. Under the high intensity of UV-C laser, the optimal reaction efficiency was achieved at pH = 7.0 with PS concentration of 1.0 mM, and the degradation efficiency for IOX reached 93.8% within only 40 s. Both bicarbonate and chloride ions could inhibit the three ICMs degradation and the inhibition rate increased with the increase of ions concentration The kinetic models were established and the steady-state concentrations of radicals were calculated D. functional theory (DFT) calculations combined with experiments were used to derive the reaction pathways for three ICMs. Cyclic voltammetry measurements detected a lower redox potential peak in IOX degradation, revealing the existence of electron shuttles under the UV-C laser irradiation to promote the redox reaction. This study is the first report of UV-C laser activation of persulfate. It is a new advanced oxidation process mediated by very effective photolysis and active species formation.

Science of the Total Environment published new progress about Alkalinity. 117-96-4 belongs to class isoquinoline, name is Diatrizoic Acid, and the molecular formula is C11H9I3N2O4, Recommanded Product: Diatrizoic Acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem