Tag: M.W:100-200

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

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

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

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

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

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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《New synthesis of the benzothiazole and benzoxazole rings》. Authors are Jenkins, Glenn L.; Knevel, Adelbert M.; Davis, Charles S..The article about the compound:2-Ethylbenzo[d]oxazolecas:6797-13-3,SMILESS:CCC1=NC2=CC=CC=C2O1).COA of Formula: C9H9NO. Through the article, more information about this compound (cas:6797-13-3) is conveyed.

HC(OEt)3 (37 g.), 22 g. 2-H2NC6H4SH, and 0.7 g. concentrated H2SO4 heated (oil bath) to 115-30° with distillation of EtOH, heating continued 1 hr. to 170-80° with distillation of 31 ml. EtOH, the mixture heated 45 min. at 175-85°, and the cooled product distilled in vacuo gave benzothiazole, C6H4.X.CR:N (I, X = S, R = H), b754 183°. Similarly were prepared the tabulated I in 75-86% yields (X, R, and b.p./mm. given): S, Me, 151°/15; S, Et, 132°/18; O, H, 182°/753; O, Me, 91°/18; O, Et, 129°/23.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Llinares, Jeanine; Galy, Jean Pierre; Faure, Robert; Vincent, Emile Jean; Elguero, Jose published the article 《Structure and reactivity of benzoxazoles: carbon-13 nuclear magnetic resonance study》. Keywords: benzoxazole structure reactivity NMR; oxazole structure reactivity NMR; aminophenol structure NMR; phenol amino structure NMR; substituent oxazole derivative NMR.They researched the compound: 2-Ethylbenzo[d]oxazole( cas:6797-13-3 ).Quality Control of 2-Ethylbenzo[d]oxazole. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:6797-13-3) here.

Thirty-four benzoxazoles, oxazole, and 10 o-aminophenols were studied by 13C NMR spectroscopy. All the signals are attributed to substituent effects. The structures of the products obtained by the nitration of benzoxazole were determined by 13C NMR. The shifts induced by substitution at the 2 position are discussed as a function of an empirical model by using the structural parameters F, R, and Q*. Azido-tetrazole equilibrium (N3 in position 2) and prototropic tautomerism (NH2, OH, and SH in position 2) are also discussed. The chem. shifts and coupling constants of oxazole and unsubstituted benzoxazole are compared.

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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 《Alkylation of furan with olefins. VI. Examination of products of alkylation of furan with olefins by gas chromatography》. Authors are Hillers, S.; Andersons, A.; Berzina, A..The article about the compound:1-(Furan-2-yl)propan-1-onecas:3194-15-8,SMILESS:O=C(C1=CC=CO1)CC).Category: benzoxazole. Through the article, more information about this compound (cas:3194-15-8) is conveyed.

cf. CA 59, 1564h, 5106g. Alkyl furans were identified by gas chromatography at 120-50° in a 3.3-m. long column filled with Celite 545 containing 25% silicone E 301 or dinonyl phthalate. The flow rate of the carrier gas (He) was 1.5 l./hr. The alkyl furans were identified by means of the relation between the log of the retention volume and the number of C atoms in the side chains. In the preparation of chromatographic standards the following new furan derivatives were prepared: 2-propionylfuran (I) hydrazone, b5 91°; I semicarbazone, m. 154°; 2-propyl-5-furylmercuri chloride, m. 99°; 2-butyrylfuran (II) hydrazone, b5 95°; II semicarbazone, m. 180-1°; 2-butyl-5-furylmercuri chloride, m. 77°.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Safety of 2-Ethylbenzo[d]oxazole. 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. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita-Baylis-Hillman carbonates.

An expedited method was developed for the diastereoselective synthesis of highly functionalized alkyl-azaarene systems with good yield and high diastereoselectivity (>15:1 dr). The methodol. includes a synergistic catalysis event involving organometallic (10 mol% AgOAc) activation of an alkyl azaarene and Lewis base (10 mol% DABCO, 1,4-diazabicyclo[2.2.2]octane) activation of a Morita-Baylis-Hillman carbonate. The structure and relative configuration of a representative product were confirmed by X-ray anal. The synthesis of the target compounds was achieved by a reaction of (alkyl)benzoxazole derivatives, such as 2-ethyl-6-(nitro)benzoxazole, 5-chloro-2-ethyl-6-nitrobenzoxazole, 2-(ethyl)oxazolo[5.4-b]pyridine, 4-methyl-3-nitropyridine, with Morita-Baylis-Hillman carbonates, such as β-[[(1,1-dimethylethoxy)carbonyl]oxy]-α-(methylene)benzenepropanoic acid ester derivatives

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem