Day: April 13, 2022

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1-(Furan-2-yl)propan-1-one, is researched, Molecular C7H8O2, CAS is 3194-15-8, about Copper(I)-catalyzed N-H olefination of sulfonamides for N-sulfonyl enaminone synthesis.Product Details of 3194-15-8.

Copper-catalyzed N-H olefination of sulfonamides for enaminone synthesis using saturated ketones as olefin sources was reported. With TEMPO derivatives and O2 as oxidants, this method provided an efficient way to produce various enaminones in good yields. Mechanistic studies helped figure out the stable intermediates and develop novel methodologies for the difunctionalization of saturated ketones.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some reactions of nitriles as acid anammonides》. Authors are Holljes, Edward L. Jr.; Wagner, E. C..The article about the compound:2-Ethylbenzo[d]oxazolecas:6797-13-3,SMILESS:CCC1=NC2=CC=CC=C2O1).Category: benzoxazole. Through the article, more information about this compound (cas:6797-13-3) is conveyed.

Nitriles may be considered as ammono-acid “”anhydrides”” or acid anammonides. They react with ο-C6H4(NH2)2 (I), with 1,3-diamines such as 1,8-C10H6(NH2)2 (II) and ο-H2NC6H4CONH2 (III), or with ο-HOC6H4NH2 (IV) with formation of heterocyclic ring derivatives similar to the Ladenburg type as effected by means of carboxylic acids or their anhydrides. It is found that the initial step is the addition of proton to the nitrile, forming a reactive cation: RCN+H+ ⇌ [RC:NH ⇔ RCNH]+. When I and PhCN (V) are refluxed for 24 hrs. or heated in a sealed tube at 200° for 6 hrs. no reaction takes place. When, however, I.HCl is used, 72% 2-phenylbenzimidazole (VI), m. 287-8°, is formed. In the same way the following 2-substituted benzimidazoles are prepared: H, 5.9% yield, m. 170.5°; Me, 27.3%, m. 173.6°; Et, 58.8%, m. 172°; Pr, 71%, m. 157-9°; Bu, 47.4%, m. 150°; Am, 50%, m. 162°; p-MeC6H4, 70.9%, m. 266-9°. The rate of the reaction depends upon the ratio of acid to nitrile and with a ratio of 1:1 NH4Cl is formed which also promotes the reaction. The reaction of I with nitriles proceeds as follows: I.HCl + RCN ⇌ I + RC(:NH)Cl (VII); VII + I → ο-HCl.H2NC6H4NHC(:NH)R (VIII); VIII → ο-HN.C6H4.N:CR (IX) + NH4Cl. The formation of VII is proven by the fact that when I and PhC(:NH.HBr)Br or PhC(:NPh)Cl (X) are heated to 100°, 56% or 57% VI is formed. X, b3 146°, m. 37°, is prepared in 80-90% yield according to a modified method of Wallach (Ann. 184, 79(1877)). When I and X are allowed to react for 1 hr. at below 5°, 68% N-phenyl-N’-ο-amino-phenylbenzamidine-HCl is formed which softens at 126-40° and, when heated at 200° or allowed to stand for 2 weeks at room temperature, gives quantitatively VI and PhNH2, indicating that VIII is an intermediate product. While the formation of VIII and IX takes place very rapidly, the formation of VII is the rate-determining step. When I and VII (R = Ph) are allowed to react in ligroin (70-90°), VI and PhC(:NPh)NHPh (XI) are formed. XI and I.HCl at 200° give 46% VI but in the absence of HCl no VI can be isolated. The analogy between acids, anhydrides, amidines and nitriles and their ability to form IX from I are shown in the following scheme: When 2.16 g. IV and 1.09 g. V are refluxed for 24 hrs. or heated at 200° for 9 hrs., 54% or 51% ο-O.C6H4.N:CPh (XII), m. 102.5-3.5°, is formed. When IV.HCl is used, 72% XII is obtained in 2 hrs. The following 2-substituted benzoxazoles (XIII) are prepared: Me, 33.5% yield, b12 59-60°; Et, 61.2%, b2 75-6°; Bu, 49.7%, b20 68-70°; Am, 52.6%, b2 114-14.5°; p-MeC6H4, 72%, m. 114°. 2-Furonitrile and 2,6-(MeO)2C6H3CN fail to give XIII. In this case too, the reaction is promoted by the presence of H ions. The course of the reaction is as follows: IV.HCl + RCN → IV + VII → ο-HOC6H4NHCR:NH (XIV) or ο-H2NC6H4OCR:NH (XV) + HCl, XIV or XV heated in the presence of HCl → XIII. The formation of VII is shown by the fact that when IV and X are heated up to 100°, 58% XII is formed. When IV and VII are allowed to react in CHCl3 at a low temperature, 82% of a compound, C19H16N2O.HCl, is formed from which 72% free base (XVI), pale yellow needles, m. 80-90°, (picrate, m. 134° (corrected)) is isolated by decomposition with alkali. XVI is found to be identical with XIV but it is not methylated by CH2N2, probably due to chelation of the OH group (cf. Herzig, et al., Ber. 39, 1557(1906); Monatsh. 25, 511(1904)). II.2HCl (2.31 g.) and 0.01 mol. MeCN heated in a sealed tube for 4 hrs. give 46.7% 2-methylperimidine-HCl: 2-Pr derivative is formed in 37% yield. The course of the reaction is the same as in the formation of XIII. III, when heated with Ac2O, PrCO2H or BzOH for 3 hrs. at 200° gives 36.2% 2-methyl- (XVII), m. 239-41°, 31.9% 2-propyl- (XVIII), m. 200-2°, or 18% 2-phenyl-3,4-dihydro-4-quinazolone (XIX), m. 217-19°. III.HCl and MeCN, PrCN or PhCN for 2 hrs. at 200° give 19.7% XVII, 22.6% XVIII or 18.5% XIX. III and MeCN give less than 6% XVII. The ring closure may occur through an addition product, ο-H2NOCC6H4NHC(:NH)R. It is suggested that in the formation of 2-substituted quinazolones from ο-H2NC6H4CO2H and nitriles in which the nitrile N enters into the ring, an intermediate of the structure, ο-HO2CC6H4NHCR:NH ⇌ ο-HO2CC6H4N:CRNH2 is formed instead of ο-H2NC6H4CONHCOR (cf. Bogert and Hand, Am. Chem. J. 24, 1931(1902)).

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

COA of Formula: C38H24F4O4P2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, is researched, Molecular C38H24F4O4P2, CAS is 503538-69-0, about Enantioselective Total Syntheses of (-)-Taiwaniaquinone H and (-)-Taiwaniaquinol B by Iridium-Catalyzed Borylation and Palladium-Catalyzed Asymmetric α-Arylation. Author is Liao, Xuebin; Stanley, Levi M.; Hartwig, John F..

We report a concise, enantioselective total synthesis of (-)-taiwaniaquinone H (I) and the first enantioselective total synthesis of (-)-taiwaniaquinol B (II) by a route that includes asym. palladium-catalyzed α-arylation of a ketone with an aryl bromide that was generated by sterically controlled halogenation via iridium-catalyzed C-H borylation. This asym. α-arylation creates the benzylic quaternary stereogenic center present in the taiwaniaquinoids. The synthesis was completed efficiently by developing a Lewis acid-promoted cascade to construct the [6,5,6] tricyclic core of an intermediate common to the synthesis of a number of taiwaniaquinoids. Through the preparation of these compounds, we demonstrate the utility of constructing benzylic quaternary stereogenic centers, even those lacking a carbonyl group in the α-position, by asym. α-arylation.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Recommanded Product: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, is researched, Molecular C38H24F4O4P2, CAS is 503538-69-0, about SynPhos in asymmetric hydrogenation. Author is Bulliard, Michel.

A review. The account briefly reviews the asym. hydrogenation industry structure in pharmaceuticals and steps necessary for the introduction of a new technol. The application of two newly patented C2 atropisomeric ligands, SynPhos and Difluorphos, in asym. hydrogenation of diketones and hydroxyketones in comparison to other chiral ligands, such as BINAP, is discussed. SynPhos is shown to be flexible in its use, general enough to cover a wide range of processes and currently positioned in the market place as a standard ligand and for as many applications as possible.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Miyajima, Atsuko; Sakemi-Hoshikawa, Kazue; Usami, Makoto; Mitsunaga, Katsuyoshi; Irie, Tomohiko; Ohno, Yasuo; Sunouchi, Momoko published an article about the compound: 2-Mercapto-5-methylbenzimidazole( cas:27231-36-3,SMILESS:SC1=NC2=CC(C)=CC=C2N1 ).Category: benzoxazole. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:27231-36-3) through the article.

We examined the effects of thyrotoxic rubber antioxidants, 2-mercaptobenzimidazole (MBI, 0.3 mmol/kg/day) and its Me derivatives, methyl-MBIs [4-methyl-MBI (4-MeMBI, 0.6 mmol/kg/day), 5-methyl-MBI (5-MeMBI, 0.6 mmol/kg/day), and 4(or 5)-methyl-MBI (4(5)-MeMBI, 0.6 or 1.2 mmol/kg/day)], on the drug-metabolizing activity in male rat liver microsomes by 8-day repeated oral administration. The weight of liver and thyroid were increased by all the test chems.; MBI was most potent, and there was no additive or synergistic effect between 4-MeMBI and 5-MeMBI. MBI decreased the cytochrome P 450 (CYP) content, NADPH-cytochrome P 450 reductase (POR) activity, 7-ethoxycoumarin O-deethylation (ECOD) activity, and flavin-containing monooxygenase (FMO) activity, but increased the 7-pentoxyresorufin O-depentylation (PROD) activity, suggesting inhibition of the drug-metabolizing activity on the whole but induce some activities such as the CYP2B activity. On the contrary, all the methyl-MBIs increased the CYP content, CYB5 content, ECOD activity, 7-ethoxyresorufin O-deethylation (EROD) activity, and PROD activity, indicating that they are mostly inducible of the CYP activity. However, the methyl-MBIs decreased the FMO activity, and 5-MeMBI and 4(5)-MeMBI appeared inhibitory for CYPs 2C11 and 2C13. Between 4-MeMBI and 5-MeMBI, there was no additive or synergistic effect on the drug-metabolizing activity, but was counteraction. It was concluded that MBI and methyl-MBIs had both inhibitory and inducible effects on the drug-metabolizing activity in rat liver microsomes at thyrotoxic doses. The effects of 4(5)-MeMBI indicated that the increased liver weight alone can be a hepatotoxic sign but not an adaptive no-adverse response in toxicity studies. The present results were related to the toxicokinetic profiles of MBI and 4(5)-MeMBI in the repeated toxicity studies.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 27231-36-3, is researched, SMILESS is SC1=NC2=CC(C)=CC=C2N1, Molecular C8H8N2SJournal, Article, Toxicology Reports called Inhibitory and inductive effects of 4- or 5-methyl-2-mercaptobenzimidazole, thyrotoxic and hepatotoxic rubber antioxidants, on several forms of cytochrome P450 in primary cultured rat and human hepatocytes, Author is Miyajima, Atsuko; Kuroda, Yukie; Sakemi-Hoshikawa, Kazue; Usami, Makoto; Mitsunaga, Katsuyoshi; Irie, Tomohiko; Ohno, Yasuo; Sunouchi, Momoko, the main research direction is cytochrome P450 4MeMB 5MeMB hepatocyte Primary culture benzimidazole; 3-MC, 3-methylcholanthrene; 4(5)-MeMBI, 4(or 5)-methyl-2-mercaptobenzimidazole; 4-MeMBI, 4-methyl-2-mercaptobenzimidazole; 5-MeMBI, 5-methyl-2-mercaptobenzimidazole; AhR, aryl hydrocarbon receptor; Benzimidazole; CYP, cytochrome P450; Cytochrome P450; DMSO, dimethyl sulfoxide; Drug-metabolizing activity; EROD, 7-ethoxyresorufin O-deethylation; Hepatocyte; MBI, 2-mercaptobenzimidazole; PXR, pregnane X receptor; Primary culture; T6βH, testosterone 6β-hydroxylation.Product Details of 27231-36-3.

Effects of 4-methyl-2-mercaptobenzimidazole (4-MeMBI) and 5-methyl-2- mercaptobenzimidazole (5-MeMBI) on cytochrome P 450 (CYP) activity were examined in primary cultured rat hepatocytes. Hepatocytes from male Wistar rats were cultured in the presence of 4-MeMBI or 5-MeMBI (0-400μM), and the activity of CYPs 3A2/4 (48 and 96 h) and 1A1/2 (48 h) was determined by measuring the activity of testosterone 6β-hydroxylation and 7-ethoxyresorufin O-deethylation, resp. As a result, 4-MeMBI and 5-MeMBI (≥12.5μM) inhibited CYP3A2 activity. On the other hand, 4-MeMBI (≥25μM) and 5-MeMBI (≥100μM) induced CYP1A1/2 activity, being consistent with the previous in vivo results. In a comparative metabolism study using primary cultured human hepatocytes from two Caucasian donors, 4-MeMBI and 5-MeMBI induced the activity of CYPs 3A4 and 1A1/2 with individual variability. It was concluded from these results that 4-MeMBI, 5-MeMBI and MBI caused inhibition of CYP3A2 activity in primary cultured rat hepatocytes, suggesting their potential for metabolic drug-drug interactions. Primary cultured rat and human hepatocytes were considered to be useful for the evaluation of effects of the benzimidazole compounds on their inducibility and inhibitory activities of cytochrome P 450 forms.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Related Products of 503538-69-0. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, is researched, Molecular C38H24F4O4P2, CAS is 503538-69-0, about Au(I)-catalyzed enantioselective 1,3-dipolar cycloadditions of munchnones with electron-deficient alkenes. Author is Melhado, Asa D.; Luparia, Marco; Toste, F. Dean.

The catalytic enantioselective 1,3-dipolar cycloaddition of munchnone dipoles with electron-deficient alkenes is described. The reaction is catalyzed by chiral bis(phosphine)gold(I) benzoate complexes and provides Δ1-pyrrolines, e.g., I, with excellent regio-, diastereo-, and enantioselectivity. The reaction is proposed to proceed through a 1,3-dipole generated by deprotonation of a gold(I)-activated azlactone.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Synthesis and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of 2,4,5-trisubstituted imidazoles, benzo[d]imidazoles, benzo[d] oxazoles and azo-linked benzo[d]oxazoles.SDS of cas: 6797-13-3.

Amino glucose-functionalized silica-coated NiFe2O4 nanoparticles (NiFe2O4@SiO2@amino glucose) were chem. synthesized and characterized by transmission electron microscope (TEM), X-ray diffraction (XRD), thermal gravimetric anal. (TGA), energy dispersive X-ray anal. (EDX), vibrating sample magnetometer (VSM), Zetasizer and Fourier transform IR spectroscopy (FT-IR) instruments. NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of 2,4,5-trisubstituted imidazoles through one-pot multicomponent condensation of benzil or benzoin, ammonium acetate with aryl aldehydes and for the synthesis of benzoxazoles using condensation reaction of 2-aminophenol with aryl aldehydes under solvent free condition. In the other study, this synthesized magnetically reusable catalyst was introduced as a new avenue for the synthesis of benzo[d]imidazoles using the reaction between aryl aldehydes and 1,2-diaminobenzene. These compounds were obtained in high yields and short reaction times. The catalyst could be easily recovered and reused for five cycles with almost consistent activity. Synthesized compounds were characterized by their phys. constant, comparison with authentic samples, FT-IR, 1H NMR, 13C NMR spectroscopy and elemental anal.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

COA of Formula: C9H9NO. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Biomimetic Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazole via the Group Transfer of Tetrahydrofolate Models. Author is Wen, Xueshan; Chen, Jianxin; Zhao, Yanqin; Chang, Xingmao; Ma, Jiachun; Zheng, Wenjun.

2-Substituted benzimidazoles, benzoxazoles I [R = Et, n-Pr, i-Pr, etc.; X = NH,O], and 2-cyclohexylbenzothiazole were prepared in good yields by biomimetic reaction of o-phenylenediamine/o-aminophenol/o-aminothiophenol with imidazolium iodides as tetrahydrofolate model compounds at the oxidation level of formate. The reaction probably involved nucleophilic addition to the C=N bond at the imidazolium ring followed a 1,3-H migration at imidazolidine intermediate and a salt elimination. This biomimetic synthesis method offers advantages such as good yields of products, easy work-up, mild reaction conditions without the use of oxidants, acid, catalyst or microwave irradiation

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Category: benzoxazole. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-Mercapto-5-methylbenzimidazole, is researched, Molecular C8H8N2S, CAS is 27231-36-3, about Electrochemical study of 2-mercaptoimidazole as a novel corrosion inhibitor for steels. Author is Alvarez-Bustamante, R.; Negron-Silva, G.; Abreu-Quijano, M.; Herrera-Hernandez, H.; Romero-Romo, M.; Cuan, A.; Palomar-Pardave, M..

From electrochem. methods, polarization resistance and electrochem. impedance spectroscopy, the corrosion susceptibility of pipeline steel samples immersed in 1 M H2SO4 was determined using nil and different concentrations of the mol. 2-mercaptoimidazole (2MI). A corrosion inhibiting efficiency, IE, value of 98.5% was reached when the 2MI concentration in the system increased to 25 ppm. Also, at this concentration, the 2MI IE was measured as a function of time finding that the IE kinetics follows the relation: %IE = 98.5-0.03t after 800 h of evaluation. During the 1st 200 h 2MI IE was higher that 90% then, it decreased to 70% and it remained constant up to 1200 h. This compound can affect both the anodic and cathodic processes, thus it can be classified as a mixed-type inhibitor however, from variation of both corrosion potential and polarization resistance with [2MI] it was possible to state that the anodic reaction rate, of the corrosion process, decreases at a greater proportion than the cathodic one. 2MI follows an adsorption mechanism, which can be adequately described by the Langmuir isotherm with an adsorption standard free energy difference (ΔG°ads) of -26.8 kJ mol-1. To analyze the influence of substituting groups, both electron-donating and electron-attracting and the number of π-electrons on the corrosion inhibiting properties of organic mols., an electrochem. study was carried out on four different mols. having similar chem. framework structure: 2-mercaptoimidazole (2MI), 2-mercaptobenzoimidazole (2MBI) 2-mercapto-5-methylbenzimidazole (2M5MBI) and 2-mercapto-5-nitrobenzimidazole (2M5NBI). The IE order followed by the mols. tested was 2MI > 2MBI > 2M5MBI > 2M5NBI. Thus 2MI turned out to be the best inhibitor, even superior to the 2MBI. This fact strongly suggests that, contrary to a hitherto generally suggested notion, an efficient corrosion inhibiting mol. does not require to be a large one, also bearing an extensive number of π-electrons.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem