Month: April 2022

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Chemical shifts in proton NMR spectra of 2-substituted furans and electrophilic constants σp+, published in 1980-07-31, which mentions a compound: 3194-15-8, mainly applied to furan NMR LFER; substituent constant NMR furan, SDS of cas: 3194-15-8.

Published values of substituent-induced chem. shift changes (Δδ) at H-5 of 2-substituted furans were correlated with σp+ constants by Δδ = 0.654 σp+ – 0.017. This equation was then used to find the σp+ constants of 15 substituents, including heterocyclic and oxime-containing groups.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Zhong, Feng; Xue, Qi-Yan; Yin, Liang researched the compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole( cas:503538-69-0 ).Electric Literature of C38H24F4O4P2.They published the article 《Construction of Chiral 2,3-Allenols through a Copper(I)-Catalyzed Asymmetric Direct Alkynylogous Aldol Reaction》 about this compound( cas:503538-69-0 ) in Angewandte Chemie, International Edition. Keywords: chiral allenol preparation copper catalyst asym alkynylogous aldol; aldol reaction; alkynylogous reaction; allenes; asymmetric catalysis; copper. We’ll tell you more about this compound (cas:503538-69-0).

Chiral 2,3-allenols were constructed through copper(I)-catalyzed asym. direct alkynylogous aldol reaction. With aromatic and heteroaromatic aldehydes, the alkynylogous aldol reaction with (R)-DTBM-SEGPHOS as the ligand proceeded smoothly to furnish the products in excellent regioselectivity with good to high diastereoselectivity and excellent enantioselectivity. In the cases of aliphatic aldehydes, esters of but-2-yn-1-ol as the substrates and (R,R)-Ph-BPE as the ligand are crucial to get good to high regio- and diastereoselectivity. The produced chiral 2,3-allenols are easily transformed into synthetically useful 2-furanones through cyclization. Finally, the developed method was successfully applied in the rapid synthesis of two chiral intermediates toward the synthesis of two pharmaceutically active compounds that are proposed for the treatment of neurol. disorders.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-(Furan-2-yl)propan-1-one( cas:3194-15-8 ) is researched.Formula: C7H8O2.Ho, Chi-Tang; Coleman, Edward C. published the article 《Chemistry of baked potato flavor: further identification of heterocyclic compounds in the volatile flavor of baked potato》 about this compound( cas:3194-15-8 ) in Journal of Food Science. Keywords: potato baked volatile flavor; odor potato baked. Let’s learn more about this compound (cas:3194-15-8).

The gas chromatog. fractions of a baked potato flavor that was isolated from 540 lb of Idaho Russet Burbank potatoes were analyzed by IR and mass spectrometry. Nine furans, 2 oxazoles, 3 thiophenes, 2 pyrroles, 2 pyridines, 1 dioxolane, and 1 trioxane were identified. Heterocyclic compounds with formyl or acetyl substituents had a characteristic nutty aroma.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Synthetic Route of C9H9NO. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Site-Selective and Stereoselective C(sp3)-H Borylation of Alkyl Side Chains of 1,3-Azoles with a Silica-Supported Monophosphine-Iridium Catalyst. Author is Murakami, Ryo; Iwai, Tomohiro; Sawamura, Masaya.

Site-selective and stereoselective C(sp3)-H borylation of alkyl side chains of 1,3-azoles with bis(pinacolato)diboron was effectively catalyzed by a silica-supported monophosphine-iridium catalyst. The borylation occurred under relatively mild conditions (2 mol% Ir, 50-90°), affording the corresponding primary and secondary alkylboronates. This system was applicable to a variety of 1,3-(benzo)azoles such as thiazoles, oxazoles, and imidazoles.

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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: 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