Category: 2199-44-2

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some reactions of 2,4-dimethylmagnesylpyrrole》. Authors are Ingraffia, F..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).Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

Because of the anomalous behavior of magnesylpyrrole with SOCl2 (I) and CS2 (cf. Oddo and Mingoia, C. A. 21, 1458), it was decided to study their action as well as that of ClCO2Et (II) on a little studied derivative of pyrrole, viz., 2,4-dimethylpyrrole (III) in the form of its magnesyl derivative (IV), and on magnesylpyrroles with neg. radicals (to stabilize the ring). IV and II in anhydrous Et2O, heated, and decomposed with ice, yield Et 2,4-dimethyl-5-pyrrolecarboxylate, HN.CMe:CH.CMe:CCO2Et (V), slightly yellow, m. 124°. I in Et2O added to ice-cold IV (2 mols.) in Et2O, after standing decomposed with ice, neutralized with NaHCO3 and purified with difficulty (Et2O, petr. ether, Me2CO and C6H6), yields 3,5,3′,5′-tetramethylpyrro-(2,2′)-sulfone, (HN.CMe:CH.CMe:C)2SO2, dark violet, decomposes around 95° stable toward hot alk. hydroxides, is not reduced by Zn and AcOH, is decomposed with evolution of H2S by Sn in hot HCl. Ag derivative, probably an α’-derivative IV and CS2 in Et2O heated, decomposed with ice, acidified with H2O4, the Et2O-soluble product treated with aqueous NaOH, and acidified when ice-cold, precipitates 2,4-dimethyl-5-dithiopyrrolecarboxylic acid, HN.CMe:CH.CMe:CC(:S)SH (VI), also obtained directly but very impure by drying the Et2O-soluble portion (loc. cit.). It is unstable and immediately oxidizes to 2,4-dimethylthiopyrrole disulfide, [HN.CMe:CH.CMe:CC(:S)S-]2, red, m. 156°. With neutral Pb(OAc)2, the aqueous Na salt (VII) of VI precipitates the Pb salt, [HN.CMe:CH.CMe:CC(:S)S]2Pb, yellow. In darkness, aqueous VI and AgNO3 precipitate the Ag salt, HN.CMe:CH.CMe:CC(:S)SAg, brick-red. No Zn salt is precipitated from aqueous VII and Zn(OAc)2. It was then to be determined whether with a compound containing a neg. CO2Et group, e. g., V, the reaction with EtMgBr is normal, and if so to determine the behavior of the new metal derivative in comparison with III. Actually V and EtMgBr in anhydrous Et2O evolve C2H6 and form the magnesyl derivative (VIII), BrMgN.CMe:CH.CMe:CCO2Et or HN.CMe:C(MgBr).CMe:CCO2Et, yellowish oil. Heated with CS2 or with AcCl in anhydrous Et2O, VIII remains unaltered. This incapacity to react probably depends upon the assumption of the enolic form, N:CMe.CH:CMe.C:C(OMgBr)OEt, as was found with alkyl pyrryl ketones by Oddo (C. A. 19, 2492; Gazz. chim. ital. 40, ii, 15(1910); cf. C. A. 4, 2460).

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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: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ) is researched.Quality Control of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.Takaya, Hikaru; Kojima, Sachiko; Murahashi, Shun-Ichi published the article 《Rhodium Complex-Catalyzed Reaction of Isonitriles with Carbonyl Compounds: Catalytic Synthesis of Pyrroles》 about this compound( cas:2199-44-2 ) in Organic Letters. Keywords: isonitrile reaction ketone rhodium catalyst; pyrrole preparation isonitrile reaction ketone rhodium catalyst. Let’s learn more about this compound (cas:2199-44-2).

Low-valent rhodium complexes are efficient catalysts for the activation of α-C-H bond of isonitriles. Addition of isonitriles to carbonyl compounds proceeds under mild and neutral conditions to give the corresponding α,β-unsaturated formamides. Catalytic synthesis of pyrroles can be performed by cyclocondensation of isonitriles with 1,3-dicarbonyl compounds Et 3,4,5-trimethyl-2-pyrrolecarboxylate was obtained in 68% yield and converted to octamethylporphyrin by a standard method.

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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.Monti, Donato; Sleiter, Giancarlo researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).Category: thiazolidine.They published the article 《Electrophilic heteroaromatic substitutions. XI. Thallium in pyrrole chemistry. Formation of C-pyrrylthallium derivatives》 about this compound( cas:2199-44-2 ) in Gazzetta Chimica Italiana. Keywords: pyrrole thallation substituent effect; pyrrylthallium derivative. We’ll tell you more about this compound (cas:2199-44-2).

Reaction of several pyrrole derivatives with Tl(III) salts was investigated under different exptl. conditions. C-Thallation is dependent on what position (α or β) of the pyrrole nucleus is amenable to attack, and on the nature of the thallating agent. Yields are strongly influenced by electronic and steric effects of the substituents already present in the pyrrole nucleus and by the nature of the reaction medium. Spectroscopic and anal. data for the C-pyrrylthallium derivatives prepared are reported. E.g., treating pyrroles I (R = H; R1 = Me, Et) with Tl(OAc)3 in MeCN or CH2ClCH2Cl gave 37-79% I [R = (AcO)2Tl; same R1].

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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, Journal of Medicinal Chemistry called Structure-Activity Relationships of (4-Acylpyrrol-2-yl)alkanoic Acids as Inhibitors of the Cytosolic Phospholipase A2: Variation of the Substituents in Positions 1, 3, and 5, Author is Lehr, Matthias, which mentions a compound: 2199-44-2, SMILESS is O=C(C1=C(C)C=C(C)N1)OCC, Molecular C9H13NO2, Application In Synthesis of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

Derivatives of 3-(1,3,5-trimethyl-4-octadecanoylpyrrol-2-yl)propionic acid (1) and (1,3,5-trimethyl-4-octadecanoylpyrrol-2-yl)acetic acid (4) were prepared and evaluated for their ability to inhibit the cytosolic phospholipase A2 of intact bovine platelets. While replacement of one of the Me groups in position 1, 3, or 5 of the acetic acid 4 by a benzyl residue did not influence the inhibitory potency significantly, the introduction of a dodecyl chain led to compounds which even enhanced the enzymic activity. Stepwise elongation of the alkyl substituent in position 1 showed that the ability to inhibit the enzyme was lost when the alkyl chain exceeded a length of five carbons in case of compound 1 or six carbons in case of compound 4. Introduction of a polar functional group at the end of the 1-alkyl chain of these inactive pyrroles, however, restored or even elevated inhibitory potency. The most preferable of the polar terminal functions investigated was the carboxylic acid moiety. 6-[2-(2-Carboxyethyl)-4-dodecanoyl-3,5-dimethylpyrrol-1-yl]hexanoic acid (65c) and 6-[2-(carboxymethyl)-4-dodecanoyl-3,5-dimethylpyrrol-1-yl]nonanoic acid (66f) were to the synthesized inhibitors with the greatest potency. With IC50 values of 3.4 and 3.3 μM, resp., they were about 3-fold more active than the standard cPLA2 inhibitor arachidonyl trifluoromethyl ketone (IC50: 11 μM).

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Paine, John B. III; Dolphin, David published an article about the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC ).COA of Formula: C9H13NO2. 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:2199-44-2) through the article.

(Cyanovinyl)pyrroles I (R = Me, R1 = Et, octyl; R = Et, R1 = Me) derived from the Knoevenagel condensation of benzyl 5-formyl-2-pyrrolecarboxylates with NCCH2CO2Me were employed in a facile sequence of 4 steps to produce, regioselectively, 2-pyrrolecarboxaldehydes II, important intermediates for porphyrin synthesis. Each step proceeded in 90-95% yield, making II available smoothly from benzyl 5-methyl-2-pyrrolecarboxylates in 7 steps, with an overall yield of 66-72%.

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Related Products 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 The effect of electron-withdrawing groups on 15N and 13C chemical shifts: A density functional study on a series of pyrroles. Author is Mothana, B.; Ban, F.; Boyd, R. J.; Thompson, A.; Hadden, C. E..

Electron-withdrawing groups (EWGs) on the nitrogen atom of pyrroles have significant effects on the properties of the pyrrole. It has been suggested that the exptl. 13C chem. shifts show a general increase in deshielding effect with the increase of N-EWGs strength [A. Thompson, S. Gao, G. Modzelewska, D.S. Hughes, B. Patrick, D. Dolphin, Organic Lett., 2, 3587 (2000)]. However, recently observed 15N chem. shifts of pyrroles do not correlate with the N-EWG strength. To elucidate the relationship between the electronic structures of pyrroles and their nitrogen and carbon chem. shifts, d. functional theory calculations were performed on pyrroles with various substituents. A correlation between the paramagnetic shift and the 15N chem. shift was observed for the pyrroles, indicating that the nitrogen chem. shift trend for the pyrroles arises entirely from variations of the paramagnetic shift contribution. However, a general correlation between the 15N chem. shifts and the EWG strength does not exist. Natural chem. shielding (NCS) anal. shows that the changes in the σ(N5-R)-π* transitions and changes in the sum of the σ(C1-N5)-π* and σ(C4-N5)-π* transitions account for the nitrogen chem. shift trend observed in the pyrroles.

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 2199-44-2, is researched, Molecular C9H13NO2, about New fluorescent chemosensor for Zn2+ ions on the basis of 3,3′-bis(dipyrrolylmethene), the main research direction is fluorescent chemosensor zinc ion dipyrrolylmethene.Product Details of 2199-44-2.

Luminescence study of the reaction of 3,3′-methanediylbis(2,4,7,8,9-pentamethyldipyrrolylmethene) (H2L) with a number of metal salts showed that this compound is an efficient fluorescent chemosensor for Zn2+ ions in organic solvents. The selectivity and sensitivity of H2L were estimated in various solvents in the presence of other metal cations (Na+, Mg2+, Co2+, Ni2+, Cu2+, Cd2+, Hg2+, Pb2+).

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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 Some transformations of 2,4-dimethylpyrrole, published in 1923, which mentions a compound: 2199-44-2, mainly applied to , Recommanded Product: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

From 0.9 g. 2,4-dimethylpyrrole (I) and 0.8 g. MeCN in cold Et2O saturated with dry HCl and allowed to stand 1 day is obtained 0.7 g. of the ketimine, m. 100°, sublimes 100° (HCl salt, green needles), of 2,4-dimethyl-5-acetylpyrrole (II). The ketimine is reduced by H and Pt sponge in alc. to I and when boiled with H2O to disappearance of the NH3 odor, 0.7 g. of it gives 0.3 g. II, m. 121°. 2,4-Dimethyl-5-chloroacetylpyrrole (0.9 g. from 1 g. I and 1 g. MeCN in cold Et2O saturated with dry HCl and allowed to stand 0.5 hr. in ice), m. 143°, gives in alc. with 30% NHMe2 after 0.5 hr. at 100° the 5-dimethylaminoacetyl derivative, m. 110°, while 0.5 g. boiled 0.5 min. in alc. with 40% HCHO and a few drops concentrated HCl yields 0.4 g. bis-[2,4-dimethyl-5-chloroacetylpyrryl]methane, m. 258°, which with NHMe2 in alc. gives the bis-5-dimethylaminoacetyl derivative m. 170°. I (1 g.) boiled up several times with 2 g. of 90% HCO2H and 10 drops of 20% HClO4 and allowed to stand 1 day gives 0.5 g. of the perchlorate, becomes discolored 200°, does not m. 260°, of bis-[2,4-dimethyl-pyrryl]methene, yellow, m. 117°. 2,4-Dimethyl-5-carbethoxypyrrole (III), obtained in 60-70% yield from I and EtMgBr and subsequent treatment with ClCO2Et, m. 125°, gives a positive Ehrlich aldehyde reaction in the cold, is hydrolyzed by boiling 50% KOH to the free acid, m. 136°, also obtained from the above Grignard compound with CO2. 2,4-Dimethyl-5-carbethoxypyrrole-3-aldehyde (IV). obtained in 85% yield from III and HCN in cold Et2O saturated with dry HCl and subsequent decomposition of the resulting imide chloride with hot H2O, m. 145°, gives a faint Ehrlich aldehyde reaction in the cold, more strongly on heating; 3 g. heated with 1:1 KOH until completely dissolved (about 15 min.) gives 2.2 g. of the free 5-carboxyaldehyde, m. 230°, which on distillation in vacuo yields 2,4-dimethylpyrrole-3-aldehyde, m. 126°, gives a positive aldehyde reaction even in the cold. Phenylhydrazone of IV, m. 204°. Azlactone, C19H18O4N2 (1.3 g. from 1.2 g. IV, 1.8 g. hippuric acid, 2.2 g. NaOAc and 20 cc. Ac2O heated 35 min. on the H2O bath), m. 232°. Oxime, m. 196-7°, converted by boiling NaOAc-Ac2O into the nitrile, C10H12O2N2, m. 171°. Semicarbazone, m. 285° (decomposition), converted by Na in alc. after 8 hrs. at 160-70° into 2,3,4-trimethylpyrrole. 2,4-Dimethyl-5-carbethoxy-3-chloroacetylpyrrole, from III and ClCH2CN, m. 163°, gives a faint positive Ehrlich reaction on heating, is highly sternutatory when powdered, gives in boiling alc. with aqueous KCN the 3-cyanoacetyl derivative, m. 172-3°.

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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 Isolation and characterization of a novel tetrahydro-[2,2′]bipyrrolyl dimer as an impurity from a Knorr reaction. Author is Thompson, Alison; Alattar, Yousef; Beshara, Cory S.; Burley, Rodney K.; Cameron, T. Stanley; Robertson, Katherine N..

A dimer, tetra-Et 2,2′,3,3′-tetramethyl-1,1′,2,2′-tetrahydro-4H,4’H-2,2′-bipyrrolyl-5,5,5′,5′-tetracarboxylate (I), has been isolated as an impurity from a Knorr reaction for the synthesis of Et 3,5-dimethylpyrrole-2-carboxylate from 2,4-pentanedione and di-Et oximinomalonate in a dissolving zinc reduction The solid-state structure of I was determined by X-ray crystallog. Knorr reactions typically rely upon the requisite pyrrole being the only water-insoluble crystalline material present in the reaction mixture, and so work-up and purification procedures for Knorr reactions should be monitored carefully given the water-insolubility of this dimer.

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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).Name: 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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