Tag: M.W=100-200

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Dihydropyridines. VII. Reactions of symmetrically alkylated 3,5-dicyanopyridines with sodium borohydride》. Authors are Kuthan, J.; Janeckova, E..The article about the compound:Pyridine-3,5-dicarbonitrilecas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1).SDS of cas: 1195-58-0. Through the article, more information about this compound (cas:1195-58-0) is conveyed.

cf. ibid. 1495; CA 60, 6817d. NaBH4 reduction of 3,5-dicyanopyridines I-VI gave 3,5-dicyano-1,2- and 1,4-dihydropyridines VII-XVII. I and LiAlH4 gave a mixture of VII and VIII which was separated by chromatography. Two procedures were used in the reduction of I-VI: Method A. EtOH (0.2 ml.) was added to a mixture of 38 mg. NaBH4 and 0.001 mole ground I-VI, and the precipitated product washed with 2.5 ml. cold H2O. Method B. NaBH4 (150 mg.) was added to a mixture of 0.002 mole I-VI and 5 ml. EtOH, the solution diluted with H2O to ∼80 ml. after several hrs., and the precipitated filtered off (starting compound, method, product, % yield, and m.p. given): I, B, VIII, 62, 205-6° (dilute EtOH); I, A, VII, 188-9° (Me2CO-cyclohexane) (VIII was also obtained); II, A, IX, 50, 214-15° (dilute EtOH); III, A, X + XI (92:8), 44, 154-72° (mixture); IV, B, XII, 89, 232-3° (MeOH); V, B, XIV + XV (71:29), 69, 138-69° (mixture); VI, -, XVI + XVII (86:14), 77, 108-22° (mixture). Similar results were obtained by reduction of I-IV with LiAlH4. Oxidation of 1.73 g. 3,5-dicyano-2-methyl-4-ethyl-1,2-dihydropyridine in 70 ml. EtOH with Ag2O from 7 g. AgNO3 gave 91% 3,5-dicyano-2-methyl-4-ethylpyridine (XVIII), m. 68-8.5°, sublimed 55-60°/0.4 mm. Treatment of 1.28 g. XVIII with MeMgI prepared from 750 mg. Mg and 1.9 ml. MeI gave 61% XVII, m. 101-2° (dilute acetone), which was oxidized with MnO2 to VI, m. 70-1°.

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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.Hartman, Tomas; Sturala, Jiri; Cibulka, Radek researched the compound: Pyridine-3,5-dicarbonitrile( cas:1195-58-0 ).Synthetic Route of C7H3N3.They published the article 《Two-Phase Oxidations with Aqueous Hydrogen Peroxide Catalyzed by Amphiphilic Pyridinium and Diazinium Salts》 about this compound( cas:1195-58-0 ) in Advanced Synthesis & Catalysis. Keywords: green chem oxidation amphiphilic pyridinium diazinium salt catalyst; oxidation aqueous hydrogen peroxide amphiphilic pyridinium diazinium salt catalyst. We’ll tell you more about this compound (cas:1195-58-0).

Amphiphilic pyridinium and diazinium salts were shown to be effective catalysts in two-phase (water/chloroform or water/dichloromethane) sulfoxidations and N-oxidations with hydrogen peroxide under mild conditions. This unprecedented oxidation method utilizes covalent bonding of hydrogen peroxide to a simple pyridinium or diazinium nucleus to increase the lipophilicity of the hydroperoxide species and to subsequently activate it for oxidations in a non-polar medium. The catalytic efficiency was found to depend on the type of heteroarenium core and on the lipophilicity of the catalyst. Five series of heteroarenium catalysts were prepared and investigated: 1-Alkyl-3,5-dicyanopyridinium, 1-alkyl-3,5-dinitropyridinium, 1-alkyl-3-cyanopyrazinium, 1-alkyl-4-cyanopyrimidinium and 1-alkyl-4-(trifluoromethyl)pyrimidinium triflates (alkyl=butyl, hexyl, octyl, decyl, dodecyl and hexadecyl). Among them, the 1-octyl-3,5-dinitropyridinium and 1-decyl-4-(trifluoromethyl)pyrimidinium triflates were found to be superior catalysts, showing the best stability and the highest catalytic activity, achieving acceleration by a factor of 350 relative to the non-catalyzed reaction. In contrast to other organocatalytic two-phase oxidations that use hydrogen peroxide, the presented method is characterized by high chemoselectivity and low catalyst loading (5 mol%) and with the reactions being performed under mild conditions, i.e., at 25° using diluted hydrogen peroxide and a non-basic aqueous phase. The catalysts have simple structures and are readily available from com. materials. Practical applications are demonstrated via the oxidation of several types of sulfides and amines.

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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, Article, Chemical Communications (Cambridge, United Kingdom) called Ruthenium-catalyzed synthesis of N-substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines, Author is Zheng, Yanling; Nie, Xufeng; Long, Yang; Ji, Li; Fu, Haiyan; Zheng, Xueli; Chen, Hua; Li, Ruixiang, which mentions a compound: 7661-33-8, SMILESS is O=C1N(C2=CC=C(Cl)C=C2)CCC1, Molecular C10H10ClNO, HPLC of Formula: 7661-33-8.

The first example of synthesis of N-substituted lactams I (R = Ph, 4-(propan-2-yl)phenyl, 2H-1,3-benzodioxol-5-yl, naphthalen-2-yl, etc.; n = 1,2,3) and N-(p-tolyl)isoindolin-2-one via an acceptorless dehydrogenative coupling of diols HO(CH2)2(CH2)nCH2OH and [2-(hydroxymethyl)phenyl]methanol with primary amines RNH2 in one step, which was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene-phosphine-phosphine ligand as the catalyst have been reported.

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COA of Formula: C3H3ClN2O2S. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1H-Pyrazole-4-sulfonyl chloride, is researched, Molecular C3H3ClN2O2S, CAS is 438630-64-9, about A robust and facile method for desulfonation to amines. Author is Li, Chen; Huang, Yilei; Cao, Sheng; Luo, Yunhao; Zhang, Ying; Yang, Guang.

In this study, a robust and facile method for desulfonation to achieve secondary amines is demonstrated. Diphenylphosphine (Ph2PH) was shown to significantly expedite the cleavage of sulfonamides under basic conditions. Aromatic and aliphatic sulfonamides were cleanly converted, with a rapid reaction time, into the required amines with good to excellent chem. yields. Moreover, the functional groups tested were generally well tolerated.

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HPLC of Formula: 7661-33-8. 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: 1-(4-Chlorophenyl)pyrrolidin-2-one, is researched, Molecular C10H10ClNO, CAS is 7661-33-8, about Synthesis and pharmacological evaluation of benzamide derivatives as potent and selective sigma-1 protein ligands. Author is Donnier-Marechal, Marion; Carato, Pascal; Larchanche, Paul-Emmanuel; Ravez, Severine; Boulahjar, Rajaa; Barczyk, Amelie; Oxombre, Benedicte; Vermersch, Patrick; Melnyk, Patricia.

A series of novel N-(aminoalkyl)benzamide derivatives such as I [m = 2, 3; R1 = Me; R2 = Bn, (CH2)2C6H4; R1R2 = (CH2)4, (CH2)2O(CH2)2, (CH2)2NMe(CH2)2, etc.; R3 = H, 4-n-Bu, 4-Cl, etc.] and N-benzyl-N-methyl-propan-1-amine derivatives II [X = CH2NH, SO2NH, NHC(O)] was designed, synthesized and pharmacol. evaluated. In vitro competition binding assays against sigma proteins (sigma-1 S1R and sigma-2 S2R) revealed that most of them conferred S2R/S1R selectivity toward without cytotoxic effects on SY5Y cells, especially with compounds I [m = 2, 3; R1 = Me; R2 = Bn]. Some selected compounds were also evaluated for their agonist and antagonist activities on a panel of 40 receptors and results showed the importance of the nature and the position with halogeno atom on the benzamide scaffold, the length chain and also the contribution of the hydrophobic part on the amine group. Among them, compounds I [m = 2, 3; R1 = Me; R2 = Bn; R3 = 4-Cl, 4-CN, 4-NO2] showed excellent affinity for S1R (Ki = 1.2-3.6 nM), selectivity for S2R (Ki up to 1400 nM) and high selectivity index (IC50(SY5Y)/Ki(S1R) ratio from 28/000 to 83/000). Furthermore, these compounds I and II presented an excellent safety profile over 40 other receptors.

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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-(4-Chlorophenyl)pyrrolidin-2-one, is researched, Molecular C10H10ClNO, CAS is 7661-33-8, about Rhodium(III)-Catalyzed C-H Vinylation of Arenes: Access to Functionalized Styrenes.Name: 1-(4-Chlorophenyl)pyrrolidin-2-one.

An effective method were developed for Rh(III)-catalyzed direct vinylation of arenes to give functionalized styrenes, using vinyltriethoxysilane as a convenient and inexpensive vinyl source. A wide variety of substrates, including 1-aryl-2-pyrrolidinones, anilines, benzamides and ketones were compatible with this reaction. Moreover, this method can be applied to the two-step synthesis of functionalized indoles. Mechanistic investigation reveals that the reaction probably proceeds through an oxidative Heck/desilylation pathway.

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Reference of Pyridine-3,5-dicarbonitrile. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Photochemistry of matrix-isolated 5-cyano-2H-pyran-2-one (δ-cyano-α-pyrone) and cyanocyclobuta-1,3-diene. Author is Menke, Jessica L.; McMahon, Robert J..

Matrix-isolation photochem. (λ > 299 nm; Ar, 10 K) of 5-cyano-2H-pyran-2-one (5, δ-cyano-α-pyrone) shows complete conversion to a mixture of several ring-opened ketene isomers (6) and a ring-closed Dewar lactone (7), as detected by IR spectroscopy. Subsequent irradiation (λ > 200 nm) causes decarboxylation of the Dewar lactone (7) to produce cyanocyclobuta-1,3-diene (8). Continued irradiation (λ > 200 nm) results in the photodecomposition of cyanocyclobuta-1,3-diene (8) to cyanoacetylene and acetylene. 4-Cyanopyridine (10) was explored as an alternative photochem. precursor to cyanocyclobuta-1,3-diene (8). It was found, however, that 10 does not exhibit observable photochem. under our irradiation conditions.

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Quality Control of Pyridine-3,5-dicarbonitrile. 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: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Substituted thieno[2,3-d]pyrimidines as adenosine A2A receptor antagonists.

A novel series of benzyl substituted thieno[2,3-d]pyrimidines, e.g. I, were identified as potent A2A receptor antagonists. Several five- and six-membered heterocyclic replacements for the optimized methylfuran were explored. Select compounds effectively reverse catalepsy in mice when dosed orally.

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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 The reduction of pyridine derivatives with lithium aluminum hydride, published in 1953, which mentions a compound: 1195-58-0, mainly applied to , Safety of Pyridine-3,5-dicarbonitrile.

When pyridine derivatives (I) with CO2Et or CN groups at the 3- and 5-positions are treated with LiAlH4 (II) the ring system is attacked first; when the 2-, 4-, and 6-positions are substituted, the functional group are reduced. The reductions are carried out by adding a large excess of II in ether to the I in absolute ether with stirring and ice-cooling, treating the mixture with saturated NH4Cl solution, and evaporating the washed ether solution Reduction of 5 g. di-Et 2,6-lutidine-3,5-dicarboxylate in 50 cc. ether with 780 mg. II in 40 cc. ether gives 40% Et 3-hydroxymethyl-2,6-lutidine-5-carboxylate, m. 100-1°; when the mixture is refluxed 2 hrs. 65% 3,5-bis(hydroxymethyl)-2,6-lutidine, m. 141-2°, is obtained. Reduction of di-Me dinicotinate gives 50% di-Me 1,4-dihydrodinicotinate, m. 150-60°, λmaximum 220, 375 mμ (MeOH). Reduction of di-Me 2-methyl-dinicotinate also gives a dihydro derivative, b0.02 115-20°, yellow needles, m. 126°, λmaximum 220, 375 mμ (MeOH). Reduction of 10 g. 2-chloropyridine (III) with 1 g. II at 0° gives unchanged III. Reduction of 1 g. Et picolinate gives 2-pyridine methanol (picrate m. 159°). Reduction of Et 2-pyridyl-acetate gives 2-pyridineëthanol, b15 120° (picrate, m. 120°). Refluxing 50 g. dinicotinic acid with 150 cc. SOCl2 15 hrs. and treating the acid chloride with NH4OH give 26 g. diamide, m. 302°, which, warmed in 130 cc. C5H5N with 19 cc. POCl3 3 hrs at 60°, yields 15 g. dinitrile (IV), m. 113° after sublimation at 70°/1 mm. Reduction of 1 g. IV in 20 cc. ether with 300 mg. II in 10 cc. ether gives 1,4-dihydrodinicotinonitrile, yellow crystals, m. 197°, λmaximum 360 mμ (MeOH). Similar reduction of 0.43 g. 2,6-lutidine-3,5-dicarbonitrile gives the 1,4-dihydro derivative, yellow crystals, m. 225°, λmaximum 362.5 mμ (MeOH). Catalytic hydrogenation of 0.5 g. IV in 20 cc. MeOH 3 hrs. with 50 mg. PtO2, 0.5 g., gives a dihydro derivative with λmax. 360 mμ which reduces neutral AgNO3. Adding (0.5 hr.) 6.5 g. II in 300 cc. ether to 46 g. Me nicotinate in 300 cc. ether at 0°, decomposing the mixture with NH4Cl, and distilling the residue of the ether extract give 31.3 g. 3-pyridine methanol, b0.1 110° (picrate, m. 158-60°). The difference in the behavior of the pyridine esters and nitriles toward II is explained as resulting from the different polarization of the pyridine rings in these compounds

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Reference of Pyridine-3,5-dicarbonitrile. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Thermodynamic Parameters of Elementary Steps for 3,5-Disubstituted 1,4-Dihydropyridines To Release Hydride Anions in Acetonitrile. Author is Zhao, Hui; Li, Yang; Zhu, Xiao-Qing.

A series of 3,5-disubstituted 1,4-dihydropyridine derivatives including the derivative with two chiral centers, 6H (R2 = CH3, CH2Ph), as a new type of organic hydride source were synthesized and characterized. The thermodn. driving forces (defined as enthalpy changes or standard redox potentials) of the 6 elementary steps for the organic hydrides to release hydride ions in acetonitrile were measured by isothermal titration calorimeter and electrochem. methods. The impacts of the substituents and functional groups bearing the N1 and C3/C5 positions on the thermodn. driving forces of the 6 elementary steps were examined and analyzed. Moreover, the results showed that the reaction mechanism between the chiral organic hydride and activated ketone (Et benzoylformate) was identified as the concerted hydride transfer pathway based on the thermodn. anal. platform. These valuable and crucial thermodn. parameters will provide a broadly beneficial impact on the applications of 3,5-disubstituted 1,4-dihydropyridine derivatives in organic synthesis and pharmaceutical chem.

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