Category: 2199-44-2

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 Synthesis of a chiral 3,3′-di-tert-butyl-2,2′-bipyrrole, published in 2003-06-30, which mentions a compound: 2199-44-2, mainly applied to chiral bipyrroledicarboxylate derivative preparation x ray; crystal structure chiral bipyrroledicarboxylate derivative; mol structure chiral bipyrroledicarboxylate derivative; atropisomer bipyrroledicarboxylate derivative preparation x ray, Product Details of 2199-44-2.

Di-Et 3,3′-di-tert-butyl-4,4′-dimethyl-2,2′-bipyrrole-5,5′-dicarboxylate (I) was synthesized in four steps from Et 3,5-dimethyl-1H-pyrrole-2-carboxylate. The CH2 hydrogens of the Et ester groups of the former are diastereotopic in the 1H-NMR, consistent with axial chirality of the bipyrrole and restricted rotation about the 2,2′-bipyrrole bond, due to the tert-Bu groups. X-ray anal. of crystalline I shows that the pyrrole rings are twisted out of coplanarity by 84.5°.

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Reference:
Thiazolidine – 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 《Infrared absorption studies. XI. NH-H and NH-O bonds》. Authors are Buswell, A. M.; Downing, J. R.; Rodebush, W. H..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).Related Products of 2199-44-2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

cf. C. A. 34, 4663.8. Data are given for the IR absorption of acetylglycine Et ester in solution and for the solid, for 3,5-dimethyl-2-carbethoxypyrrole in solution, for diphenylamine in CCl4 solution, for the solids and for mixtures of diphenylamine and dimethylacetamide and for solid films of acetamide, trichloroacetamide, n-valeramide, sulramic acid, glycine and diketopiperazine. These data indicate that intermol. NHN bonds show a fundamental IR absorption near 3 μ. These bonds are formed only when the first N is relatively much more acidic than the second N. NH-O bonds are formed only with a semipolar O. The bonding observed by IR studies in amides and the peptide linkage is believed to be NHO- with absorption near 3.0 μ if isolated but at 3.22 μ if the bonds are formed in pairs. A coplanar structure is postulated for the CONHR group which involves geometrical isomerism. This structure must be considered in any explanation of protein behavior.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Category: thiazolidine. 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: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Nuclear magnetic resonance study of carbethoxypyrroles.

The chem. shifts and the ring proton coupling constants of various substituted carbethoxypyrroles are reported. The electron-withdrawing effect of the carbethoxy groups shifts the resonances of the ring substituents to low field while the inductive and mesomeric effects of the Me groups shift the resonances to higher field. The deshielding effect is more pronounced with 2-carbethoxypyrroles than for 3-carbethoxypyrroles. The ring proton spin-spin coupling constants depend on the nature of substituents and increase with the electronegativity of the substituents. In some cases, long-range coupling between the Me side-chain protons and ring protons was observed.

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Reference:
Thiazolidine – Wikipedia,
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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 a series of substituted 2-ethoxycarbonylpyrroles, published in 2002-06-30, which mentions a compound: 2199-44-2, Name is Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, Molecular C9H13NO2, Recommanded Product: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

The synthesis of 2-(ethoxycarbonyl)-3,4-dimethylpyrrole (I) was studied. A series of substituted 2-(ethoxycarbonyl)pyrrole was prepared by reaction of oxo olefin salt with di-Et aminomalonate. For example, refluxing MeCOCMe:CHONa with di-Et aminomalonate in aqueous HOAc for 2 h gave 35% I.

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Reference:
Thiazolidine – 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 《Kinetics of pyrrole substitutions. Iodination reaction》. Authors are Doak, Kenneth W.; Corwin, Alsoph H..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).Reference of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

The rates of iodination of 4 substituted pyrroles, measured in aqueous dioxane (28% dioxane by weight) at 26.5 ± 0.1°, follow 2nd-order equations. The substituents are methyl and carbethoxy groups. Reduction rates of 2 iodopyrroles with HI are also reported, one of which follows a 3rd order. From the data obtained it is shown that the α-position is about 25 times as reactive as the β-position. N-Methyl substitution increases the reactivity of the pyrrole ring 8 to 15% thus the effect is smaller than that of Me substitution on benzene. Similar studies of the reduction rates show the α-position to be 20 times as reactive towards reduction as the β-position. The iodination equilibrium constant K = [RI] [HSolv+] [I-]/[RH] [Solv] [I2], assuming the solvent as 48.2 M, is 24 for α-iodination and 21 for β-iodination, thus apparently little affected by structural changes.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate(SMILESS: O=C(C1=C(C)C=C(C)N1)OCC,cas:2199-44-2) is researched.Related Products of 1273-73-0. The article 《A new and practical synthesis of pyrroles》 in relation to this compound, is published in Tetrahedron Letters. Let’s take a look at the latest research on this compound (cas:2199-44-2).

Heating γ-nitro ketones bearing an electron-withdrawing group such as an ester geminal to the nitro group with formamidinesulfinic acid (reducing agent) and triethylamine in isopropanol produces pyrroles in good yield. The reductive cyclocondensation of α-nitro-δ-oxo-β-phenylbenzenepentanoic acid ester gave 3,5-diphenyl-1H-pyrrole-2-carboxylic acid Et ester (85% yield).

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Category: thiazolidine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about The reaction of β-aminoenones with α-amino derivatives. Synthesis of 2-functionalized pyrroles. Author is Alberola, Angel; Andres, Jose M.; Gonzalez, Alfonso; Pedrosa, Rafael; Vicente, Martina.

β-Aminoenones react with Et glycinate, α-aminoacetonitrile and α-aminoacetamide hydrochlorides leading to 2-functionalized pyrroles. Although the transamination is a high-yield process, the transformation of the intermediate, in both basic or thermally induced conditions, affords the corresponding pyrroles in poor to moderate yields. Thus, transamination of AcCH:CMeNH2 with EtO2CCH2N+H3 in MeOH gave 89% AcCH:CMeNHCH2CO2Et which on cyclization in EtONa/EtOH gave 33% Et 3,5-dimethyl-2-pyrrolecarboxylate.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Related Products of 2199-44-2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Detection and Prevention of Aggregation-based False Positives in STD-NMR-based Fragment Screening. Author is Vom, Amelia; Headey, Stephen; Wang, Geqing; Capuano, Ben; Yuriev, Elizabeth; Scanlon, Martin J.; Simpson, Jamie S..

Aggregation of small organic compounds is a problem encountered in a variety of assay screening formats where it often results in detection of false positives. A saturation transfer difference-NMR-detected screen of a com. available fragment library, followed by biochem. assay, identified several inhibitors of the enzyme ketopantoate reductase. These inhibitors were subsequently revealed to be aggregation-based false positives. Modification of the fragment screen by addition of detergent in the saturation transfer difference-NMR experiments allowed an assay format to be developed that resulted in the identification of genuine hit mols. suitable for further development.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Preliminary work to the ring syntheses of porphyrins, etc. III. Several pyrrole compounds with amino groups and unsaturated side chains》. Authors are Fischer, H.; Zeile, Karl.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).Reference of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

cf. C. A. 24, 5302. 2,4-Dimethyl-3-amino-5-carbethoxypyrrole (I) yields an Ac derivative, m. 201° (60% yield). With iso-AmNO2, I gives 90% of the diazonium chloride, decomposes at 173°; it is not completely decomposed by boiling with H2O for 1 hr.; continued boiling, especially with Cu powder, gives 2,4-dimethyl-5-carbethoxypyrrole, m. 125°. Hydrolysis of I with 10% NaOH gives 2,4-dimethyl-3-amino-5 carboxypyrrole (II), which begins to split off CO2 at 75°; Ac derivative, m. 203° (decomposition). 2,4-Dimethyl-3-aminopyrrole, m. 127°, results in about 50% yield by warming the moist II at 75°; Ac derivative, m. 205°. The bromination product of the Ac derivative of I, heated with H2O, gives nearly quant. bis(3-acetylamino-4-methyl-5-carbethoxy-2-dipyrryl)methane, m. 251°, crystallizing in different forms from EtOH, Ac2O and dilute AcOH. With HCO2H and Fe powder, this yields an amorphous 1,4,5,8-tetramethyl-2,3,6,7 tetraacetylaminoporphin. II, HCO2H and HBr, heated 2-3 min., give (2,4-di-methyl-3-aminopyrryl)-2′,4′-dimethyl-3′-aminopyrrolenyl)methene tri-HBr salt, decomps over 280°; from H2O it seps. as violet crystals, from HBr in yellow-red prisms; AcONa gives the mono-HBr salt, dark violet needles, m. 234°. 2,4-Dimethyl-3-(β-carboxy-vinyl)-5-carbethoxypyrrole (III) and NaOH with a little H2O, heated over a free flame for 2 hrs. and then dry-distilled, give dimethylpyrrole and (2,4-dimethylpyrryl)(2′,4′-dimethylpyrrolenyl)methene. MeNO2 adds to 2,4-dimethyl-3-(β-nitrovinyl)-5-carbethoxypyrrole, giving the compound C12H17O6N3, m. 180°. 2,4-Dimethyl-3-(β-dicyano-vinyl)-5-carbethoxypyrrole (IV) and Br give a perbromide, golden yellow, decomposed by H2O to a 2-bromomethyl derivative, m. 258°. IV, MeOH and Br give the 2-carbomethoxy derivative, m. 187°; saponification with 0.1 N NaOH by heating 12 hrs. at 85° gives 2.5-dicarboxy-3-formyl-4-methylpyrrole, does not m. 360°; the di-Me ester m. 180° (oxime, m. 221°; semicarbazone, m. 247°). IV and SO2Cl2 in Et2O, followed by hydrolysis with H2O, give the 2-carboxy derivative, does not m. 360°; similarly III gives the 2-carboxy derivative, m. 241°; the free acid has no m. p. The Me ester of III m. 150°. 2,4-Dimethyl-3-formyl-5-carbethoxypyrrole and SO2Cl2 give the 2-carboxy-3-chloro derivative, m. 260°. 2,4-Di-methyl-3,5-diformylpyrrole (V) and 2,4-dimethyl-3-acetylpyrrole with HBr-EtOH give (2,4-dimethyl-3-formylpyrryl)(2′,4′-dimethyl-3′-acetylpyrrolenyl)methene, m. 210°. V and cryptopyrrole give with HBr 5,5′,3,3′-tetramethyl-4-ethyl-4′-formylpyrromethene-HBr, thick prisms. 2,4-Dimethyl-5-carbethoxy-3-thioformylpyrrole, for which a method of preparation is given, gives with SO2Cl2 and H2O 4-methyl-3-formyl-2-carbethoxy-5-carboxylic acid-pyrrole, m. 169°; phenylhydrazone, yellow, m. 235°.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Porphyrins. VI. The relative reactivities of substituted pyrroles》. Authors are Badger, G. M.; Harris, R. L. N.; Jones, R. Alan.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).Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

The comparative reactivities of a series of substituted pyrroles was examined by use of the diazo-coupling reaction and the Ehrlich reaction. The method used was that of Treibs and Fritz (CA 52, 13705g), but some modifications were introduced, p-AcNHC6H4N2Cl was used instead of p-PhNHC6H4N2Cl, and PhN2Cl and 2,4,6-Br3C6H2N2OAc were included to improve the accuracy of classification. Six aryldiazonium salts (I-VI) were used. With I-IV the reaction was carried out by mixing an alc. solution of the pyrrole (5 mL. 1.5 × 10-3M) with an aqueous solution of the diazonium salt (0.15 mL., 5 × 10-2M) and with V-VI an HOAc solution of the pyrrole was mixed with an HOAc solution of the Na salt of the anti-diazotate, both with and without the addition of HCl (0.15 mL., 2N). Tests were carried out at pH 3, 5, and 7 with the following pyrroles (substituents given): 3-Me; 2,4-Me2; 3-CO2Et; 2,4-Me2, 3-CO2Et; 2-Z, 3-Me, 4-CO2Et; 2-Q, 3-Me, 4-Ac; 3-CO2Et, 4-Me; 3-Ac, 4-Me; 2-CO2Et, 3,4-Me2; 2-CO2Et, 3,5-Me2; 2-CO2Et, 3,5-Me2; 2-CO2Et, 3-CH2CH2CO2Et, 5-Me; 2-CO2Et; 2-CH:C(CN)2, 3,4-Me2; 2-CH:C(CN)2, 3-CH2CH2-CO2Et, 4-Me; 2-CH:C(CN)2, 4-Me; 2-CH:C(CN)2, 3-Me; and 2-CH:C(CN)2. The results showed that the dicyanovinyl group exerted a very pronounced deactivating influence on pyrroles. The dicyanovinyl group was much more deactivating than an ethoxycarbonyl group. Most of the pyrroles used were prepared earlier. Other pyrroles were prepared as follows: A solution of 50 g. 2-carboxy-3-ethoxycarbonyl-4-methylpyrrole in ethanol-amine was refluxed 1 h. and poured into 1 l. H2O, the mixture extracted 24 h. with ether, and the aqueous solution acidified with dilute HCl to give 36 g. 2-carboxy-3-(2-hydroxyethylcarbonyl)-4-methylpyr-role (VII), m. 219° (decomposition) (EtOH). VII (2.5 g.) in 10 mL. 25% aqueous NaOH was heated 15 h. in a sealed tube at 140-50°, the mixture extracted with ether, and the extract dried and evaporated to yield 0.67 g. 3-methylpyrrole (VIII), b. 142-3°. Formylation of VIII by the Vilsmeier-Haack method at 0° yielded 2-formyl-3-methylpyrrole (IX), m. 92°. Condensation of 0.1 g. IX with 0.05 g. malononitrile in a few drops MeOH and I drop Et2NH yielded 2-(-dicyanovinyl)-3-methylpyrrole, m. 194.5-5.5° (decomposition) (MeOH). A mixture of 1 g. 2-ethoxycarbonyl-3,4-dimethylpyrrole, 1 mL. EtOH, and 10 mL. 10% aqueous KOH was refluxed 90 min. and the solution cooled and brought to pH 5-6 (HOAc) to yield 0.8 g. 2-carboxy-3,4-dimethylpyrrole (X). Refluxing 5 g. X and 5 mL. ethanolamine 1 h. and working up the mixture yielded 2.56 g. 3,4-dimethylpyrrole (XI), b760 164-6°, m. 32-3°. Formylation of XI (as in VIII) yielded 2-formyl-3,4-dimethylpyrrole (XII), m. 129-30°. XII was converted into 2-(-dicyanovinyl)-3,4-dimethylpyrrole by the method of Fischer and Hoefelman (CA 32, 33894).

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Reference:
Thiazolidine – Wikipedia,
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