Day: April 15, 2022

Quality Control of (S)-Propane-1,2-diamine dihydrochloride. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (S)-Propane-1,2-diamine dihydrochloride, is researched, Molecular C3H12Cl2N2, CAS is 19777-66-3, about Optically active derivatives of imidazolines. α-Adrenergic blocking properties. Author is Hsu, Fu-Lian; Hamada, Akihiko; Booher, Mark E.; Fuder, H.; Patil, P. N.; Miller, Duane D..

The title compounds I (R and R1 = H, Me, or PhCH2; R2 = 1-naphthylmethyl, PhCH2, or 2,6-dichloroaniline) as salts were prepared from an optically active 1,2-diamine-2HCl and an imino ester HCl, and converted to a stable solid salt. I were evaluated for α-adrenergic activity on rabbit aortic strips. Compared to naphazoline or tolazoline, substitution of a Me or PhCH2 at the 4 position of the imidazoline ring resulted in moderate α-blocking activity with no apparent stereoselectivity with such substitution.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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.Sen, Chiranjit; Ghosh, Subhash C. researched the compound: 8-Hydroxyquinoline 1-oxide( cas:1127-45-3 ).Synthetic Route of C9H7NO2.They published the article 《Transition-Metal-Free Regioselective Alkylation of Quinoline N-Oxides via Oxidative Alkyl Migration and C-C Bond Cleavage of tert-/sec-Alcohols》 about this compound( cas:1127-45-3 ) in Advanced Synthesis & Catalysis. Keywords: alkyl quinoline oxide regioselective preparation; quinoline oxide alc alkyl migration bond cleavage PIDA mediated; isoquinoline alkyl oxide regioselective preparation; alc isoquinoline oxide alkyl migration bond cleavage PIDA mediated; pyridine alkyl oxide regioselective preparation; oxide pyridine alc aalkyl migration bond cleavage PIDA mediated. We’ll tell you more about this compound (cas:1127-45-3).

An unprecedented C2-alkylation of quinoline N-oxide derivatives I [R1 = Me, Et; R2 = H, OH, HNC(O)Ph, etc.; R3 = H, 6-Me, 5-Br, etc.] via C-C bond activation of tert- and sec-alkyl alc. was described using hypervalent iodine (III) reagent PhI(OAc)2 (PIDA). This regioselective alkylation using mild hypervalent iodine reagents was more practical, operationally simple and transition metal-free. The reaction proceeded efficiently with a broad range of substrates including quinoline, isoquinoline, and pyridine N-oxides using a variety of tert-/sec- alcs. to afford compounds I, alkyl-benzo[h]quinoline-N-oxides, alkyl-pyridine-N-oxides and alkyl-isoquinoline-N-oxides. From exptl. outcome, a rationalized mechanism was proposed, mediated by PIDA.

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Quinoxaline – Wikipedia,
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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: 32717-95-6, is researched, SMILESS is C12=C(CCC3=C4CC2)[Cu+]1534[Cl-][Cu+]678(C9=C6CCC7=C8CC9)[Cl-]5, Molecular C16H16Cl2Cu2Journal, Article, Organic Letters called Asymmetric [4 + 3] Annulations for Constructing Divergent Oxepane Frameworks via Cooperative Tertiary Amine/Transition Metal Catalysis, Author is Chen, Zhi; Chen, Zhi-Chao; Du, Wei; Chen, Ying-Chun, the main research direction is oxepane framework preparation enantioselective diastereoselective; indole vinyl carbonate amine metal catalyst annulation.SDS of cas: 32717-95-6.

Asym. [4+3] annulations between isatin-derived Morita-Baylis-Hillman carbonates and two types of vinyl carbonates synergistically catalyzed by tertiary amines and transition metals, through chemoselective assemblies of in situ formed allylic ylides and metal-containing 1,4-dipoles were reported. A range of oxepane frameworks I [R1 = H, 5-Me, 5-Br, etc.; R2 = Me, Et; R3 = Me, allyl, Bn, etc.] and II [X = CF, CCH3, NH, etc.] were generally constructed in moderate to good yields with high stereocontrol. Moreover, all four diastereomers for the products bearing vicinal stereocenters were accessible by tuning tertiary amine and metal catalysts.

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Quinoxaline – Wikipedia,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《8-Hydroxy-1-methoxyquinoline methosulfate》. Authors are Krasavin, I. A.; Dziomko, V. M.; Radin, Yu. P..The article about the compound:8-Hydroxyquinoline 1-oxidecas:1127-45-3,SMILESS:OC1=CC=CC2=CC=C[N+]([O-])=C12).Synthetic Route of C9H7NO2. Through the article, more information about this compound (cas:1127-45-3) is conveyed.

The crude title compound, not described previously, m. 126-8° (decomposition) and is very soluble in water, soluble in alcs., and insoluble in nonpolar solvents. Reaction with nucleophilic compounds gives 2-substituted 8-hydroxyquinolines. A mixture of 48.3 g. powd. 8-hydroxyquinoline 1-oxide (m. 138.5-39°) (Phillips, et al., CA 51, 11349a; Murase and Demura, CA 58 3390b, recrystallized twice from water and C6H6) and 37.9 g. freshly distilled Me2SO4 is warmed on a water bath 2 hrs. with reflux. The mass is cooled and stirred until crystallization, 200 ml. dry Et2O is added, and the mixture stirred until all material is hardened. The solid is washed with 50-100 ml. Et2O in a mortar after filtration, washed on the filter with Et2O, and dried in a vacuum desiccator. Yield 77.6-9.3 g. hygroscopic material. Recrystallization of 20 g. from EtOH-Et2O gave 3.67 g., m. 143-4.5°.

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Quinoxaline – Wikipedia,
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HPLC of Formula: 221012-82-4. 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: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, is researched, Molecular C38H34N2O4P2, CAS is 221012-82-4, about Nickel-Catalyzed Asymmetric α-Arylation and Heteroarylation of Ketones with Chloroarenes: Effect of Halide on Selectivity, Oxidation State, and Room-Temperature Reactions. Author is Ge, Shaozhong; Hartwig, John F..

We report the α-arylation of ketones with a range of aryl chlorides with enantioselectivities from 90 to 99% ee catalyzed by the combination of Ni(COD)2 and (R)-BINAP and the coupling of ketones with a range of heteroaryl chlorides with enantioselectivities up to 99% ee catalyzed by Ni(COD)2 and (R)-DIFLUORPHOS. The analogous reactions of bromoarenes occur with much lower enantioselectivities. Mechanistic studies showed that the difference in the rates of decomposition of the arylnickel(II) halide intermediates to {[(R)-BINAP]NiX}2 likely accounts for the difference in the enantioselectivities of the reactions of bromoarenes and chloroarenes. This catalyst decomposition can be overcome by conducting the reactions with [(R)-BINAP]Ni(η2-NC-Ph) (4), which undergoes oxidative addition to haloarenes at room temperature

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Safety of (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, is researched, Molecular C38H34N2O4P2, CAS is 221012-82-4, about Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed α-Hydroxylation of 1,3-Ketoesters. Author is Smith, AlexanderM. R.; Rzepa, Henry S.; White, Andrew J. P.; Billen, Denis; Hii, King Kuok.

Systematic studies of reaction conditions and subsequent optimization led to the identification of important parameters for stereoselectivity in the asym. α-hydroxylation reaction of 1,3-ketoesters. Enantioselectivities of up to 98% can be achieved for cyclic substrates and 88% for acyclic ketoesters. Subsequently, the combination of cyclic/acyclic ketoester, catalyst, and oxidant was found to have a profound effect on reaction rates and turnover-limiting steps. The stereochem. of the reaction contradicts that observed for other similar electrophilic substitution reactions. This was rationalized by transition-state modeling, which revealed a number of cooperative weak interactions between oxidant, ligand, and counterion, together with C-H/π interactions that cumulatively account for the unusual stereoselectivity.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Dier Junyi Daxue Xuebao called Synthesis and antifungal activity of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-(N-butyl-N-substituted benzylamino)-2-propanol, Author is Wei, Ning; Zhao, Xiao-zhong; Chai, Xiao-yun; Guan, Zhong-jun; Dan, Zhi-gang; Yu, Shi-chong; Wu, Qiu-ye, which mentions a compound: 57825-30-6, SMILESS is CCC1=CC=C(CBr)C=C1, Molecular C9H11Br, Name: 1-(Bromomethyl)-4-ethylbenzene.

To study the antifungal activity of triazole alcs. by introducing N-Bu and substituted benzyl as side chain, fourteen title compounds were synthesized and characterized by 1H NMR, IR, and LC-MS. The MICs of the compounds were determined by in vitro test using 8 clin. pathogenic fungi. The title compounds exhibited potent antifungal activities against nearly all fungi tested (except for Aspergillus fumigatus), especially for the deep infection ones. Three compounds showed a 16-fold activity (with a MIC80 value of 0.015 6 μg/mL) as that of fluconazole against Microsporum gypseum. Two compounds showed a 128-fold activity (with a MIC80 value of 0.003 9 μg/mL) as that of fluconazole against Candida albicans, and their activities were higher than those of other pos. controls.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-(Bromomethyl)-4-ethylbenzene( cas:57825-30-6 ) is researched.Quality Control of 1-(Bromomethyl)-4-ethylbenzene.Yu, Shichong; Chai, Xiaoyun; Hu, Honggang; Yan, Yongzheng; Guan, Zhongjun; Zou, Yan; Sun, Qingyan; Wu, Qiuye published the article 《Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase》 about this compound( cas:57825-30-6 ) in European Journal of Medicinal Chemistry. Keywords: triazole preparation inhibitor cytochrome P 450 14 alpha demethylase; click reaction triazole preparation antifungal evaluation. Let’s learn more about this compound (cas:57825-30-6).

A series of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols, which are analogs of fluconazole, have been designed and synthesized as the potential antifungal agents by the click reaction. Click reaction approach toward the synthesis of two sets of novel 1,2,3-triazolyl linked triazole antifungal derivatives was achieved by Cu(I)-catalyzed 1,3-dipolar cycloaddition of propargylated intermediates with substituted benzyl or alkyl azides. The 1,2,3-triazolyl group was inserted into the side chain of the target mol. which can increase the antifungal activity of compounds

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 8-Hydroxyquinoline 1-oxide(SMILESS: OC1=CC=CC2=CC=C[N+]([O-])=C12,cas:1127-45-3) is researched.Formula: C9H7NO2. The article 《Molecular and crystal structure of 8-hydroxyquinoline N-oxide》 in relation to this compound, is published in Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry. Let’s take a look at the latest research on this compound (cas:1127-45-3).

The structure of 8-hydroxyquinoline N-oxide was determined from diffractometer data by a direct method. The compound crystallizes in the monoclinic system with space group P21/c. The cell data are: a 12.1364(4), b 4.9211(2), c 13.1384(4) Å, β 109.26(1)°, d.(calculated)=1.449, d.(exptl.)=1.46, Z=4. The structure was solved by a direct method. 1528 reflections were used in a full-matrix least-squares refinement. R was reduced to a final value of 0.053. Bond lengths between non-H atoms have estimated standard derivations (e.s.d.’s) between 0.002 and 0.003 Å. The e.s.d.’s of the various bond angles (non-H atoms) range from 0.01 to 0.02°. Distances and angles involving the H atoms have e.s.d.’s of 0.02 Å and 1°, resp. The 2 C-N distances of the quinoline ring are unusually long, and the quinoline moiety is surprisingly similar to naphthalene in terms of bond distances and angles. The inductive effect of the N-O group may in part be responsible for the C-N lengthenings. The hydroxyl H atom is bonded to the dative O atom via a short intramol. H bond. The direct relation between the N-O dative bond distance and the strength of a H bond to the dative O atom appears to be substantiated in this study.

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Quinoxaline – Wikipedia,
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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 8-Hydroxyquinoline 1-oxide, is researched, Molecular C9H7NO2, CAS is 1127-45-3, about Palladium-Catalyzed Alkenylation of Quinoline-N-oxides via C-H Activation under External-Oxidant-Free Conditions, the main research direction is palladium catalyst stereoselective regioselective alkenylation quinoline oxide.Formula: C9H7NO2.

The direct cross-coupling of quinoline-N-oxides with olefin derivatives has been realized using palladium acetate as the catalyst in the absence of external ligand and oxidant to give the corresponding 2-alkenylated quinolines and 1-alkenylated isoquinolines chemo- and regioselectively in 27-95% yield. The catalytic process is proposed to proceed via direct C-H bond activation of the quinoline-N-oxide with Pd(OAc)2 followed by Heck coupling with the olefin. The resultant N-oxide of the alkenylated quinoline can oxidize the reduced Pd(0) to regenerate the Pd(II) active species and simultaneously release the 2-alkenylated quinoline without using any external oxidants and reductants.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider