Category: isoquinoline

Adusumalli, Krishna M. S. published the artcileMe3Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines: A convenient approach for the synthesis of substituted 1-aminoisoquinolines, Application of 4-Methoxy-N-methylaniline, the main research area is aminoisoquinoline preparation trimethylaluminum reagent; benzonitrile amine tandem nucleophilic addition intramol cyclization trimethylaluminum; 1-aminoisoquinolines; 2-(2-oxo-2-phenylethyl)benzonitriles; CWJ-a-5; intramolecular cyclisation; nucleophilic addition.

A simple and efficient protocol for the construction of 1-aminoisoquinolines was achieved by treating 2-(2-oxo-2-phenylethyl)benzonitriles with amines in the presence of Me3Al. The reaction proceeds via a domino nucleophilic addition with subsequent intramol. cyclization. This method provides a wide variety of substituted 1-aminoisoquinolines with good functional group tolerance. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of the antitumor agent CWJ-a-5, I, on a gram scale.

Beilstein Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Application of 4-Methoxy-N-methylaniline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Gonzalez-Lainez, Miguel published the artcileN-Methylation of Amines with Methanol Catalyzed by Iridium(I) Complexes Bearing an N,O-Functionalized NHC Ligand, Category: isoquinoline, the main research area is iridium complex imidazolylidenelutidine polydentate ligand preparation catalyst methylation aniline; crystal structure iridium complex containing imidazolylidenelutidine polydentate ligand; mol structure iridium complex containing imidazolylidenelutidine polydentate ligand.

A set of neutral [IrBr(L2)(κC-tBuImCH2PyCH2OMe)] and cationic [Ir(L2)(κ2C,N-tBuImCH2PyCH2OMe)]PF6 (L2 = cod, (CO)2) Ir(I) compounds featuring a flexible lutidine-derived polydentate ligand having NHC and -OMe as donor functions were evaluated as catalyst precursors for the N-methylation of aniline using MeOH both as a reducing agent and a C1 source. The carbonyl complexes are somewhat more active than the related diene compounds with the neutral compound [IrBr(CO)2(κC-tBuImCH2PyCH2OMe)] being the more active. A range of aromatic primary amines, including heterocyclic amines, were selectively transformed into the corresponding N-methylamino derivatives using this catalyst at a low catalyst loading (0.1 mol %) and substoichiometric amounts of Cs2CO3 (half equiv) as a base, in MeOH at 423 K. For aliphatic primary amines, selective N,N-dimethylation was achieved under the same catalytic conditions. The unselective deprotonation of the methylene linkers in [IrBr(CO)2(κC-tBuImCH2PyCH2OMe)] affords two isomeric neutral complexes featuring a coordinated dearomatized pyridine core, which were converted into [Ir(OMe)(CO)2(κC-tBuImCH2PyCH2OMe)] upon addition of MeOH. This compound undergoes thermal activation of a C-H bond of the tert-Bu group to give the cyclometalated Ir(I) complex [Ir(CO)2{κ2C,C-(-CH2Me2C-ImCH2PyCH2OMe)}] featuring a bidentate C,C-coordinated NHC ligand. Mechanistic studies support a borrowing H mechanism proceeding through Ir(I) intermediates with the methoxo complex as the catalytic active species and the cyclometalated complex as the catalyst resting state. D labeling experiments demonstrated that both species are in equilibrium under catalytic conditions, which is consistent with the exhibited catalytic activity of the cyclometalated complex.

Organometallics published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Xu, Haiwei published the artcileDesign and synthesis of novel butenolide derivatives and inducing apoptosis in gastric cancer cells, Computed Properties of 86-51-1, the main research area is uncinine preparation antitumor gastric cancer; morpholinomethylbutenolide preparation diastereoselective antitumor apoptosis structure activity.

A new method of preparation for natural product uncinine was reported. According to the method, a series of novel butenolides derivatives I (X = O, CH2, NCH3), II (R = Me, OMe, n = 0, 1) and III [R1 = phenylmethylidene, thiophen-2-ylmethylidene, [3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]methylidene, etc.] were designed and synthesized based on the natural product Uncinine. Most of the synthetic compounds showed significant antiproliferation activity against MGC-803. Among of them, III [R1 = (4-tert-butylphenyl)methylidene] (IV) showed a potent anticancer effect with IC50 of 2.9μmol/L in gastric cancer cell MGC803 and showed good selectivity to gastric cancer cells MGC803, HGC27, SGC7901 and less cytotoxicity in a normal gastric epithelial cell line (GES1). The research on the mol. level suggests that the mechanism of compound IV inducing apoptosis in gastric cancer cells is partially dependent on activation of caspase-9/3.

Youji Huaxue published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Computed Properties of 86-51-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Kangkang published the artcileInvestigation of NNN Pincer Ruthenium(II) Complexes with a Pendant Hydroxyl Group for N-Monomethylation of amines and Nitroarenes by Methanol, Recommanded Product: 4-Methoxy-N-methylaniline, the main research area is hydroxy trinitrogen NNN pincer ruthenium preparation crystal mol structure; monomethylation amine nitroarene methanol hydroxy trinitrogen pincer ruthenium catalyzed.

A family of air- and moisture-stable NNN pincer ruthenium(II) complexes with a pendant OH were developed, which exhibit unprecedented high reactivity and selectivity in N-monomethylation of amines and nitroarenes using methanol. The study reveals adopting the combination of 1H-pyrazole-1-yl and 3,5-dimethyl-4-hydroxyethyl-1H-pyrazol-1-yl as the two assistant arms of the pyridyl-backbone is a suitable choice. The mechanism study discloses that, during the catalytic cycle, dehydrogenation of methanol to form formaldehyde is a fast and reversible step.

ChemCatChem published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Jha, Anand Mohan published the artcileOligosaccharides as green catalyst for one-pot multicomponent synthesis of spirooxindole derivatives in water, Formula: C9H10O3, the main research area is isatin isatoic anhydride amine cyclodextrin catalyst multicomponent reaction; spiroindolequinazoline preparation green chem; amine benzaldehyde isatoic anhydride cyclodextrin catalyst multicomponent reaction; phenyl quinazolinone preparation green chem.

A one pot synthetic methodol. was developed towards multicomponent synthesis of spiro[indoline-3,2′- quinazoline]-2,4′(3’H)-dione from isatoic anhydride, isatin and primary amines in aqueous medium via supramol. catalysis. An untapped potential of β-Cyclodextrin to mediate multicomponent reactions in aqueous medium was revealed. Developed protocol was further verified by extrapolating the synthetic protocol using different isatin derivatives and amine analogs. In other synthetic scheme, some compounds were synthesized by reaction of various substituted benzaldehydes, Isatoic anhydride and primary amines. Synthesized library of compounds were further characterized using various spectroscopic techniques. During all the synthetic process, the catalytic efficiency of cyclodextrin was exploited. Efficiency of all the three forms of cyclodextrins were tested to find the best reaction for synthesis of spiro compounds The usefulness of β-cyclodextrin was proved by showing its reusability. The essential role of β-cyclodextrin in the synthetic methodol. was further proved by doing the control experiments which showed that no product was formed in the absence of catalyst. The attachment of reactant mol. was also proved by doing 1H NMR of reaction mixture at different time interval in D2O. On the basis of observation, a plausible mechanistic pathway of reaction was proposed. Other two forms of cyclodextrins were also eliminated on the ground of their insuitability in the formation of desired product. Catalyst recovery procedure was established and was used without any significant loss of catalytic activity upto 5 times.

International Journal of Life Science and Pharma Research published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Chen, Xiu-Ping published the artcileStudy on the mild, rapid and selective difluorocarbene-mediated triclassification of iododifluoroacetophenone with secondary amines and tree model for product classification, Recommanded Product: 4-Methoxy-N-methylaniline, the main research area is difluoromethyl benzoimidazole preparation; indole difluoromethyl preparation; formamide aryl preparation; benzothiazole difluoromethyl thio preparation; benzooxazole difluoromethyl thio preparation; aryl difluoromethoxy preparation.

In this work, a room temperature difluorocarbene-mediated triclassification reaction of iododifluoroacetophenone and secondary amines with mild condition, short reaction time (only 10 min) and high selectivity had been studied, which produced one of the following three substances: N-CF2H derivatives I [R1 = H, SCF2H, 2-pyridyl, (3,4-dichlorophenyl)methyl; R2 = H, CN, C(O)Me, (2-chloropyrimidin-4-yl); R3 = H, 5-Br, 6-NO2, 5,6-di-Me, 6-Me-5-NO2; X = C, N; Y = C, N] (up to 87% yield), formamides ArNR4C(O)H [Ar = Ph, 4-MeOC6H4, 1-naphthyl; R4 = Me, Et] (82-89% yield) or the recycled starting secondary amines. This phenomenon was related to the structural stability of the corresponding products. If unstable, it would be hydrolyzed to formamides first, and then further hydrolyzed to starting amines. Based on the geometric structure of the raw materials, the corresponding prediction tree model was established, which provided guidance for the further application of difluoromethylation of Vemurafenib and AZD9291. In addition, this method was successfully applied to the S- and O-difluoromethylations to obtain the corresponding sulfur derivatives II [Z = S, O; R5 = 5-Cl, 6-Br, 4-Me, etc.] and O-CF2H derivatives ArO-CF2H [Ar = 3,4-di-MeOC6H3 1-naphthyl, 4-PhC6H4, etc.] with satisfactory yields.

Tetrahedron published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Yu, Haitao published the artcileDihydrolevoglucosenone as a bio-based catalytic solvent for efficient reductive-transformation of CO2 with amines into formamides and benzothiazoles, Category: isoquinoline, the main research area is formamide benzothiazole preparation; carbon dioxide amine reductive transformation dihydrolevoglucosenone bio catalytic solvent.

Transformation of CO2 as the C1 resource to produce value-added chems. is of great importance to decrease CO2 emission. In this context, development of green catalytic systems, especially those derived from renewable resources, is highly attractive to make the processes of converting CO2 more sustainable, which has gained significant interest. In this work, cellulose-derived dihydrolevoglucosenone (DLGO, Cyrene) was employed as a renewable catalytic solvent to convert CO2. DLGO was highly efficient for reductive conversion of CO2 with amines using PhSiH3 as the reductant, and various corresponding formamides could be selectively synthesized. Reaction kinetics anal. suggested that DLGO-based catalytic system possessed a higher reaction rate constant and lower apparent activation energy than both GVL and CH3CN-based catalytic systems. Furthermore, systematic studies revealed that DLGO with high polarity had strong ability to activate the N-H bond in amines and the Si-H bond in PhSiH3 by the solvent effect (i.e., solvation and polarization), thereby making the catalytic system be highly efficient. This developed biomass-based catalytic system could be expanded to synthesize benzothiazoles from the reductive conversion of CO2 with aminothiophenols using PhSiH3 as the reductant. Notably, the DLGO-based system combined CO2 transformation and biomass utilization, affording it possessing more values of practical applications.

Chemical Engineering Journal (Amsterdam, Netherlands) published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Tang, Feiying published the artcileBiomass-derived N-doped porous carbon: an efficient metal-free catalyst for methylation of amines with CO2, SDS of cas: 5961-59-1, the main research area is biomass derived nitrogen doped carbon catalytic methylation amine.

Developing green, efficient, and low-cost catalysts for methylation of N-H by using CO2 as the C1 resource is highly desired yet remains a significant challenge. Herein, N-doped porous carbons (NPCs) were designed, synthesized, and are an excellent metal-free catalyst for CO2-participated methylation conversion. NPCs were prepared via the pyrolysis of a mixture of tannic acid and urea. Both theor. calculation and the N species especially pyridinic N and pyrrolic N within NPCs can work as Lewis basic sites for attacking CO2 to weaken the C=O bonds and lower the mol. conversion barrier, facilitating the subsequent methylation of N-H to produce, for example, N,N-dimethylaniline. Besides, the unique porous structure can enrich CO2 and accelerate mass transfer, synergistically promoting the conversion of CO2. The optimized NPC(1/5) catalyst, integrating the porous structure and strong Lewis basicity, exhibits excellent catalytic activity for CO2-based methylation reaction under mild conditions (1 bar CO2, 75°). The work, for the 1st time, demonstrates the feasibility of using NPCs to catalyze the methylation of amino compounds to produce N,N-dimethylamine by exploiting CO2 as the C1 resource.

Green Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, SDS of cas: 5961-59-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Lenci, Elena published the artcileA Glucose-Derived α-Hydroxy Aldehyde for the Petasis Reaction: Facile Access to Polyfunctional δ-Amino Acids, Recommanded Product: 4-Methoxy-N-methylaniline, the main research area is glucose hydroxy aldehyde preparation multicomponent Petasis borono Mannich; polyfunctional amino acid preparation multicomponent Petasis borono Mannich.

The multicomponent Petasis borono-Mannich reaction proceeds via an imine with the boronic acid acting as the nucleophile for the preparation of amines and their derivatives, including amino acids. In view of the expansion of the poorly-exploited carbohydrate chem. using this reaction, a new α-hydroxy aldehyde moiety from the terminal diol of D-glucose diacetonide was synthesized and applied to this multicomponent reaction, demonstrating the scope of this method and the applicability to the convenient preparation of a protected polyfunctional δ-amino acid in only three synthetic steps from the Petasis reaction intermediate.

European Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Kalita, Tapasi published the artcileEthyl 2-Cyano-2-(2-Nitrophenylsulfonyloximino)Acetate (ortho-NosylOXY) Mediated One-Pot Racemization Free Synthesis of Ureas, Carbamates, and Thiocarbamates via Curtius Rearrangement, Synthetic Route of 104-01-8, the main research area is urea preparation; carbamate preparation; thiocarbamate preparation; carboxylic acid ethyl cyano nitrophenylsulfonyloximino acetate Curtius rearrangement.

A detailed NMR-based mechanism study is incorporated here. Direct conversion of to ureas RNHC(O)NHR1 (R = Ph, 4-methylphenyl, 4-methoxybenzyl, (tert-butoxycarbonylamino)(phenyl)methyl, etc.; R1 = 4-chlorophenyl, tert-Bu, methoxycarbonylmethyl, etc.), carbamates RNHC(O)OR1 (R = 4-methoxyphenyl, 4-bromophenyl; R1 = 4-nitrobenzyl, 4-methoxybenzyl), and thiocarbamate RNHC(O)SR1 (R = Ph, undecan-1-yl, 2-methoxyphenyl; R1 = 4-chlorobenzyl) in a single pot via Curtius rearrangement is accomplished. One recently established coupling reagent, ethyl-2-cyano-2-(2-nitrophenylsulfonyloximino)acetate (ortho-NosylOXY), is successfully used for the racemization free synthesis of ureas, di-peptidyl ureas, and carbamates with moderate to good yield (82-69%). This single-pot hassle-free procedure works with a diverse range of N-protecting groups Fmoc, Boc, and Cbz. Various amines R1NH2, including aromatic, Me esters of amino acids, tert-butylamine, benzyl alcs. (such as 4-nitrobenzyl alc., 4-methoxybenzyl alc.), and (4-chlorophenyl)-methanethiol, are used as nucleophiles. Racemization suppression, easy removal of byproducts, and less waste generation make this methodol. useful.

Asian Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Synthetic Route of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem