Category: thiazolidine

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Derivatives of pyrrylazobenzenearsonic acids》. Authors are Muic, N.; Fles, D..The article about the compound:Ethyl 3,5-Dimethyl-2-pyrrolecarboxylatecas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC).SDS of cas: 2199-44-2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

cf. C.A. 45, 9526a. The synthesis is essentially the same as previously described. 2,4-Dimethyl-3,5-carbethoxypyrrole (I) was prepared by the method of Knorr. I was saponified in 10% KOEt, and converted to 2,4-dimethyl-3-carbethoxy-5-pyrrolecarboxylic acid (II) by the method of Küster, et al. (C.A. 16, 3895). Decarboxylation of II by dry distillation gave 2,4-dimethyl-3-carbethoxypyrrole (III). I was also treated with concentrated H2SO4 by the method of Fischer and Walach (C.A. 20, 1620) to give 2,4-dimethyl-5-carbethoxy-3-pyrrolecarboxylic acid, which was decarboxylated by heating at atm. pressure to 2,4-dimethyl-5-carbethoxypyrrole (IV). Attempts to couple diazotized 4, 3-H2N(O2N)C6H3AsO3H2 and III were not successful; a resinous product, which could not be purified, was obtained, and III was isolated from the reaction mixture Attempts to couple a salt of diazotized 3,4-H2N(HO)C6H3AsO3H2 (V) with IV were also unsuccessful. p-H2NC6H4AsO3H2 (4.34 g.) in 50 cc. H2O containing 1.63 cc. concentrated H2SO4 was diazotized with 20 cc. N NaNO2 at 0-5° and the product filtered into 3.34 g. III in 200 cc. absolute EtOH. 4-(3-Carbethoxy-2,4-dimethyl-5-pyrrylazo)benzenearsonic acid (VI) precipitated as an orange-yellow powder. VI was filtered, rinsed with water, dissolved in aqueous NaOH, and the solution clarified with active C; acidification with dilute HCl gave 4.3 g. VI, orange-yellow microcrystals, decompose 210°, slightly soluble in water, somewhat more soluble in EtOH, nearly insoluble in C6H6 and ether, and soluble in dioxane; crystallization from dioxane gave well-formed needles. VI was precipitated from alk. solution with dilute acids. VI was stable in air under light. V (4.66 g.) in 70 cc. H2O containing 5.8 cc. concentrated H2SO4 was diazotized as above and the product filtered into 3.34 g. III in 200 cc. absolute EtOH. 2-(3-Carbethoxy-2,4-dimethyl-5-pyrrylazo)-1-phenol-4-arsonic acid (VII) precipitated, and addnl. amounts of VII were obtained on diluting with H2O. VII was then dissolved in N NaOH, the solution clarified with active C, added to 0.1 N HCl with constant stirring, and the precipitate was filtered, washed with H2O, dried, and recrystallized twice from dioxane to yield 7.2 g. VII, yellow needles, decompose 160°. VII was stable in air under light. (p-H2NC6H4)2As(:O)OH (1.46 g.) in 30 cc. H2O containing 3.7 cc. concentrated HCl was diazotized as above with 10 cc. N NaNO2 and the solution added dropwise at 5° or lower to 1.67 g. III in 70 cc. EtOH containing 5 g. NaOAc, previously dissolved in a small volume of H2O, to yield di-Et 5, 5′-[arsinobis(p-phenyleneazo)]bis[2,4-dimethyl-3-pyrrolecarboxylate] (VIII). VIII was filtered, washed with cold H2O, dried in vacuo, and recrystallized from dioxane and then from ether to yield 1 g. VIII, dark orange microcrystals, m. 151° (decomposition). VIII was soluble in EtOH, dioxane, and CHCl3. p-H2NC6H4AsO3H2 (2.17 g.) in 25 cc. H2O containing 0.81 cc. concentrated H2SO4 was diazotized with 10 cc. N NaNO2 and the product filtered into 1.67 g. IV in 200 cc. absolute EtOH; when the solution was clear 15 g. NaOAc in a small amount of H2O was added with cooling, and, after 1 hr., 4 l. H2O was added to precipitate 4-(5-carbethoxy-2,4-dimethyl-3-pyrrylazo)benzenearsonic acid (IX), yellow-orange powder. IX was twice dissolved in alkali and reprecipitated by dilute HCl, washed with water, and dried in vacuo to yield 1.2 g. IX, darkens 100°, m. 185° (decomposition), IX was soluble in EtOH and dioxane, and stable in air under light.

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Product Details of 1273-73-0. 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: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Electronic effects in the ferrocene ring system by proton magnetic resonance spectroscopy.

Results of a proton magnetic resonance study of the chem. shifts of ring protons of representative monosubstituted ferrocene compounds are reported. The substituents cover a span from strongly electron-donating groups to strongly electron-withdrawing. Some relations appear to exist between the ring-proton chem. shifts in these compounds and those reported for the corresponding monosubstituted benzene compounds The chem. shifts recorded were precisely measured. As such, they serve to revise the data reported while this work was in progress. 15 references.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of pyrrolecarboxaldehydes, published in 1956, which mentions a compound: 2199-44-2, Name is Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, Molecular C9H13NO2, Application of 2199-44-2.

HCO-NMe2 (I) (23.89 g.) and 58.25 g. POCl3 warmed after 10 min. to 60°, treated dropwise in 1.5 hrs. with 18 g. 2,4-dimethylpyrrole in an equal volume of I, the mixture stirred 1 hr. at 60°, poured into 333 g. ice and 245 g. fused NaOAc, the mixture boiled, cooled, extracted with Et2O, the extract evaporated free from Et2O and made alk. with powd. Na2CO3, filtered, and the residual product (II) dried. Further extraction of the filtrate with Et2O gave another 0.69 g. II. II boiled in petr. ether, the solution purified with C, filtered and cooled gave 0.6 g. (crude) 2,4-dimethyl-3,5-pyrroledicarboxaldehyde, m. 165-6° (from H2O), and 9.6 g. (crude) 2,4-dimethyl-5-pyrrolecarboxaldehyde, m. 89-90° (from H2O). Similarly, I and POCl3 at 60°, treated dropwise with stirring with 2,4-dimethyl-8-ethylpyrrole gave 2,4-dimethyl-3-ethyl-5-pyrrolecarboxaldehyde, m. 105-6°. In the same way, 1.79 g. I and 4.37 g. POCl3 treated with 1.35 g. 2,3,4-trimethylpyrrole gave 0.3 g. 2,3,4-trimethyl-5-pyrrolecarboxaldehyde, m. 147°; 2.6 g. I and 6.32 g. POCl3 with 3 g. Et 2,4-dimethyl-3-pyrrolecarboxylate in I yielded Et 2,4-dimethyl-5-formyl-3-pyrrolecarboxylate, m. 165°; 8.6 g. I and 21 g. POCl3 with 10 g. Et 2,4-dimethyl-5-pyrrolecarboxylate and 10 g. I produced 11.2 g. Et 2,4-dimethyl-3-formyl-5-pyrrolecarboxylate, m. 145°. Heating 20 g. 2,4-dimethyl-5-carbethoxy-3-pyrrolecarboxylate at 200° with 200 g. quinoline and 2 g. finely divided pure Cu to cessation of CO2 evolution, cooling, filtering, acidifying the filtrate with 50% HCl, filtering, washing the precipitate with H2O, and drying gave 11.2 g. Et 2,4-dimethyl-5-pyrrolecarboxylic acid, m. 122°.

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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 Decarboxylation and formylation of certain pyrrole derivatives, published in 1954, which mentions a compound: 2199-44-2, mainly applied to , Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

H2NCH2CH2OH (I) is used as decarboxylation agent for substituted carboxypyrroles. Adding 28.5 g. AcCH2CO2Et to Et α-nitroso-α-benzoylacetate (from 38.5 g. BzCH2CO2Et), then adding gradually 28.5 g. Zn dust with gentle boiling, refluxing the mixture 2 hrs., and pouring it into H2O give 63% 2-methyl-4-phenyl-3,5-dicarbethoxypyrrole, colorless prisms, m. 124-5°. 2,4-Dimethyl-3-carboxy-5-carbethoxypyrrole (II), 85%, fine prisms, m. 272° (decomposition), and 2-methyl-4-phenyl-3-carboxy-5-carbethoxypyrrole (III), 78%, platelets, m. 220° (decomposition) are prepared by partial saponification of the corresponding diesters. Refluxing 21.1 g. II and 12.2 g. I 1 hr. and pouring the mixture into H2O give 90% 2,4-dimethyl-5-carbethoxypyrrole (IV), prisms, m. 124.5-5°; similarly, III gives 84% 2-methyl-4-phenyl-5-carbethoxypyrrole, needles, m. 134.5-5°. Gradually adding 15.4 g. POCl3 to 13.4 g. IV and 7.3 g. HCONMe2, refluxing the mixture 2 hrs., pouring it into H2O, and neutralizing it with NaOAc give 95% 2,4-dimethyl-3-formyl-5-carbethoxypyrrole, needles, m. 145-5.5° (oxime, m. 199-200°; semicarbazone, decompose at about 275°). 2-Methyl-4-phenyl-3-formyl-5-carbethoxypyrrole, prepared similarly in 97% yield, prisms, m. 144.5-5° (oxime, 96%, plates, m. 210-11°; semicarbazone, needles, decompose at about 280° with sublimation).

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Application In Synthesis of 2-(7-Bromo-1H-indol-3-yl)acetic acid. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-(7-Bromo-1H-indol-3-yl)acetic acid, is researched, Molecular C10H8BrNO2, CAS is 63352-97-6, about Substituted indoleacetic acids tested in tissue cultures. Author is Engvild, Kjeld C..

Monochloro substituted indole-3-acetic acids inhibited shoot induction in tobacco tissue cultures about as much as IAA. Dichloro substituted indole-3-acetic acids inhibited shoot formation less. Other substituted indoleacetic acids except 5-fluoro- and 5-bromoindole-3-acetic acid were less active than IAA. Callus growth was quite variable and not correlated with auxin strength measured in the Avena coleoptile test.

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Quality Control of Bromoferrocene. 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: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Probing the tolerance of cucurbit[7]uril inclusion complexes to small structural changes in the guest. Author is Yi, Song; Li, Wei; Nieto, Daniel; Cuadrado, Isabel; Kaifer, Angel E..

The binding properties of the cucurbit[7]uril host with three structurally related ferrocene-containing guests, ferrocenyltrimethylammonium, ferrocenylmethyltrimethylammonium and ferrocenylethyltrimethylammonium, were studied using 1H NMR spectroscopy, mass spectrometry, voltammetry and computational methods. The exptl. and computational data indicate that the stability of the cucurbit[7]uril inclusion complexes is relatively insensitive to the number of methylenes connecting the trimethylammonium and the ferrocenyl groups, although some of their properties are affected in significant ways.

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Groves, Brandon R.; Smithen, Deborah A.; Cameron, T. Stanley; Thompson, Alison published the article 《Thionation reactions of 2-pyrrole carboxylates》. Keywords: pyrrolyl thionoester preparation; pyrrole carboxylate thionation Lawesson reagent.They researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).Computed Properties of C9H13NO2. 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:2199-44-2) here.

The reaction of 2-pyrrole carboxylates I [R = H, CH3; R1 = CH3, (CH2)4CH3, C6H5, etc.; R2 = CH3, CH2CH3, (CH2)2CH3; R3 = CH2CH3, C6H5CH2; X = O] with Lawesson’s reagent at elevated temperatures results in the corresponding thionoesters, I [X = S] concurrent with the production of a new class of pyrrole annulated with the (1,3,2)-thiazaphospholidine unit II. Addition of BF3·OEt2 to the thionation procedure was found to produce the corresponding F-BODIPY, III constituting a four-step reaction in one-pot. The scope and limitations of these reactions involving the promiscuous Lawesson’s reagent were described.

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Product Details of 2199-44-2. 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: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Synthesis of cyanopyrroles. Author is Cheng, Ling Jiang; Lightner, David A..

Regioselective synthesis of α-cyanopyrroles (vs. α-alkoxycarbonylpyrroles) using oximinocyanoacetate esters in a Knorr-type reductive condensation with β-diketones can be directed by the presence of water. Thus, HON:C(CN)CO2Me was reacted with CH2Ac2 in hot AcOH in the presence of Zn dust to give exclusively 3,5-dimethylpyrrole-2-carbonitrile when the AcOH was wet. Whereas, in glacial AcOH, only Me 3,5-dimethylpyrrole-2-carboxylate was isolated in ∼40% yield.

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Quality Control of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. 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: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Pyrrole chemistry. An improved synthesis of ethyl pyrrole-2-carboxylate esters from diethyl aminomalonate. Author is Paine, John B. III; Dolphin, David.

Pyrrole-2-carboxylates I (R = Me, Et; R1 = H, Me, Et, Pr, CH2CO2Me, CH2CH2CO2Me; R2 = Me, Et, Pr, CH2CH2CO2Et), versatile precursors for the total synthesis of both synthetic model and naturally occurring tetrapyrroles and porphyrins, were prepared in greatly improved yields by the addition of RCOCHR1COR2 and H2NCH(CO2)Et)2 to AcOH. The method is suitable for both small- and large-scale synthesis and has proved far more reliable than the in situ Zn reduction of HON:C(CO2Et)2. Yields range from 60-70% for the dominant product isomer from unsym. diketones to 75-90% for the single product derived from sym. diketones. RCOCHR1COR2 were prepared by treating RCOCHR1 with (R2CO)2O in the presence of BF3.

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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.Ates, M. Nurullah; Allen, Chris J.; Mukerjee, Sanjeev; Abraham, K. M. researched the compound: Bromoferrocene( cas:1273-73-0 ).SDS of cas: 1273-73-0.They published the article 《Electronic effects of substituents on redox shuttles for overcharge protection of Li-ion batteries》 about this compound( cas:1273-73-0 ) in Journal of the Electrochemical Society. Keywords: lithium ion battery overcharge protection ferrocene derivative redox shuttle. We’ll tell you more about this compound (cas:1273-73-0).

The redox behavior and kinetic parameters of five ferrocene derivatives were investigated in 1M LiPF6 in 50:50 volume% ethylene carbonate:Et Me carbonate, a typical electrolyte used in lithium-ion batteries. Using cyclic voltammetry and rotating disk electrode voltammetry techniques, the effect of electron donating and withdrawing substituents on each derivative was evaluated from the view point of the Hammett substituent constant We found that electrochem. rate constants of the ferrocene derivatives can be related to the Hammett equation which gives an accurate approximation for predicting the oxidation potential of redox shuttles when changes are desired in their electron donating and electron withdrawing properties by means of functional group substitution. Our results show that the exchange c.d. and reaction rate for oxidation decrease as the electron withdrawing property of the substituent increases. It is also shown that electron donating and electron withdrawing property of a substituent affect the exchange c.d. and electrochem. oxidation reaction rate obeying a trend opposite to that of the Hammett substituent constants (σ). The correlations found here are expected to improve the ability to systematically design chem. overcharge protection reagents through judicious substitution of functional groups on redox shuttles.

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