Category: 2199-44-2

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, Heterocycles called 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, which mentions a compound: 2199-44-2, SMILESS is O=C(C1=C(C)C=C(C)N1)OCC, Molecular C9H13NO2, Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

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

Jansma, Ariane; Chuan, Tiffany; Albrecht, Robert W.; Olson, Dean L.; Peck, Timothy L.; Geierstanger, Bernhard H. 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 ).Reference of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. 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.

A microflow CapNMR probe double-tuned for 1H and 13C was installed on a 400-MHz NMR spectrometer and interfaced to an automated liquid handler. Individual samples dissolved in DMSO-d6 are submitted for NMR anal. in vials containing as little as 10 μL of sample. Sets of samples are submitted in a low-volume 384-well plate. Of the 10 μL of sample per well, as with vials, 5 μL is injected into the microflow NMR probe for anal. For quality control of chem. libraries, 1D NMR spectra are acquired under full automation from 384-well plates on as many as 130 compounds within 24 h using 128 scans per spectrum and a sample-to-sample cycle time of ∼11 min. Because of the low volume requirements and high mass sensitivity of the microflow NMR system, 30 nmol of a typical small mol. is sufficient to obtain high-quality, well-resolved, 1D proton or 2D COSY NMR spectra in ∼6 or 20 min of data acquisition time per experiment, resp. Implementation of pulse programs with automated solvent peak identification and suppression allow for reliable data collection, even for samples submitted in fully protonated DMSO. The automated microflow NMR system is controlled and monitored using web-based software.

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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 《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).Category: thiazolidine. 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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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Alcoholytic, phenolytic and hydrolytic cleavage of organic compounds by catalysts. II》. Authors are Houben, J.; Fischer, Walter.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. 25, 3311. As shown recently, trihalomethyl ketones are not only converted stoichiometrically into alkali carboxylates and CHCl3 by aqueous alkali (Reaction 1) but also undergo another, purely catalytic reaction; even in the cold they react with alcs. according to the equation RCOCCl3 + R’OH = RCO2R’ + CHCl3 (Reaction 2). It was thought that an alcoholate was indispensable as the catalyst and that water must be excluded as completely as possible to prevent reaction 1. It was soon found, however, that this conception was erroneous and that the role of catalyst can be played very successfully by certain organic salts, such as alkali acetates, formates, benzoates, etc., and purely inorganic carbonates, bicarbonates, sulfites, nitrites, and reaction 2 can be smoothly effected in systems containing considerable water (10%). Thus, while BzCCl3 is not changed in the least by heating 8 hrs. at 170° in a sealed tube, addition of a droplet of dilute aqueous KOH to its MeOH solution suffices to decompose it at once, with evolution of heat, into BzOMe and CHCl3, Presumably there is first formed a little BzOK which quickly exerts its powerful catalytic effect. Mg(OH)2, shaken a long time in aqueous suspension with BzCCl3, decomposes it almost completely into (BzO)2Mg and CHCl3 but in aqueous MeOH gives 92% BzOMe. Thus, in addition to the possibility of neutralizing aqueous or aqueous alc. alkali by completely neutral compounds such as AcCCl3, BzCCl3, etc., a reaction which may prove useful for preparative and anal. purposes, there is the further possibility of decomposing, also in completely neutral solution, the excess of halogen ketone by subsequent addition of alc. It may thus be possible, by addition of minute amounts of perfectly neutral substances, to produce large quantities of nascent CHCl3, CHBr3, HCN (nitriles also undergo the reaction). The milder conditions (entire absence of strong alkalies) under which reaction 2 can now be effected has made it possible to extend the reaction to other substances which previously had either not reacted at all (phenols) or only with difficulty (menthol), for long and high heating may be employed, if necessary, and the reaction can be carried out in alk., neutral or acid solution; thus, KOAc is effective in AcOH and HCO2K reacts excellently in HCO2H. Hydrolysis of the trihalomethyl ketones can likewise be effected by aqueous solutions of catalytically small quantities of certain salts or, what amounts to the same thing, of alkalies, for these are rapidly converted by the ketone into the catalytic salt. Thus, BzCCl3 is smoothly decomposed into BzOH and CHCl3 by boiling several hrs. with water to which has been added a little KOAc; with water alone there is no hydrolysis even after 7 hrs. at 170°. Reaction 1 is really based on catalytic hydrolysis, the much slower velocity of which, as compared with the catalytic esterification (reaction 2) seems to be due to the slight solubility of the hydrolysis products; its acceleration by a stoichiometric amount of alkali (reaction 1) may in great part be due to the opportunity thus afforded to the BzOH to dissolve; in aqueous Me2CO containing a trace of KOAc, 96% BzOH was obtained from BzCCl3 after refluxing 4 hrs. The ready splitting off of a C atom from the trihalomethyl ketones does not occur with the dihalogen compounds, as far as can be judged from experiments with BzCHCl2, which yields PhCH(OH)CO2H. The following % yields of ester were obtained from the appropriate trichloromethyl ketone and alc. in the presence of a little Na: m-O2NC6H4CO2Me 62, m-H2NC6H4CO2Me 90, Et 2,4-dimethylpyrrole-5-carboxylate 93, Et 2-methylindole-3-carboxylate 85, octyl acetate 70, cetyl benzoate 45. Yield of phenol esters with KOAc as catalyst (reaction temperature in parentheses): PhOBz 80 (120°), p-MeC6H4OBz 90 (230°), o-MeC6H4CO2Bz 80 (230°), menthyl benzoate 58 (150°) (the yield previously obtained with Na was 37%). Below are given, resp., the length of reaction (in days unless otherwise stated) and the % yield of benzoate obtained at 20° from BzCCl3 with various alcs. and 0.5-1 equivalent of different catalysts. MeOH: HCO2K 2, 74; HCO2K + HCO2H 3, 85; KOAc 2, 92; KOAc + AcOH 3, 90; KOBz 1, 81; KNO3 3, 91; Mg(OH)2 1, 92. PrOH: Mg(OH)2 2, 79. iso-BuOH: KOAc 4, 90. Hexyl alc.: KOAc 4, 93. Allyl alc.: KOAc 2, 93. Menthol: KOAc 6 hrs. at 150°, 58. PhOH: 4 hrs. at 120°, 80. o-Cresol: KOAc, 4 hrs. at 130°, 80. p-Cresol: KOAc 4 hrs. at 130°, 90. Although very small amounts of the catalysts are distinctly effective, 0.5-1 equivalent was used to shorten the reaction time as much as possible. The lengths of reaction given were in many cases perhaps unnecessarily long. KHCO3, Na2CO3, Na2SO3 and AcONH4 are also effective, but KNO3, anhydrous or hydrated NH4Cl, K bioxalate, HCl.H2O, H2SO4.H2O and HCl are not effective even after 1 day at 70°. BzCCl3 (2.23 g.) and 0.5 g. KOAc, allowed to stand 1 day in 5 cc. MeOH containing 10% water, gave 81% BzOMe; 2.23 g. of the ketone and 0.5 g. KOAc shaken 25 hrs. in 2.4 cc. MeOH containing 50% water gave 22% ester and 70% unchanged ketone. When BzCHCl2 was allowed to stand with 0.1 equivalent Na in MeOH the alkalinity soon greatly diminished and Cl ions but no CH2Cl2 or BzOMe were formed; with 2 equivalents Na, NaCl was deposited and after standing overnight there was obtained 61% phenylglyoxal di-Me acetal, b13 110-4°.

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Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Related Products of 2199-44-2. 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: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Sulfur derivatives in the pyrrole series. Author is Treibs, Alfred; Schulze, Lothar; Kreuzer, Franz Heinrich; Kolm, Hans Georg.

Reaction of 2,4-dimethyl-5-(ethoxycarbonyl)pyrrole (I) with SO2 in the presence of EtBr and AlCl3 or in CH2Cl2 containing AlCl3 gave the sulfide II or the sulfoxide III, resp. Successive reaction of SCl2 with MeOH and 2-methyl-3-(ethoxycarbonyl pyrrole gave the disulfide IV. Addition of EtSH to tris[2-methyl-3-(ethoxycarbonyl)-5-pyrrolyl]methane gave the sulfide V. Addition of p-tolysulfonyl isothiocyanate to I gave the derivative VI.

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Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Application In Synthesis of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. 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 Synthesis and protonation studies of a meso-unsubstituted surfactant porphyrin.

The surfactant porphyrin I was prepared Spectroscopic studies show that intermol. protonation occurs between the side-chain carboxyl groups and the inner N atoms of I, giving a porphyrin dication. In 5 × 10-5M CHCl3 solution, 27% of the porphyrin mols. are in the dicationic form and they are self-associated with some of the remaining mols. in the free base form.

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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 Chemistry of pyrrole pigments. III. Nitrogen-hydrogen tautomerism of substituted pyrromethenes. Proton nuclear magnetic resonance spectrometric investigations. Author is Falk, H.; Gergely, S.; Hofer, O..

The temperature-, solvent-, and concentration-dependence of the NMR of the pyrromethenes(I thru VI) was examined and the chem. shifts were assigned and the long range coupling constants were determined Intra- and intermol. proton transfer was observed; tautomeric NH exchanges at -100° were too fast to be measured by NMR.

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Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Category: thiazolidine. 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 Sulfur derivatives in the pyrrole series. Author is Treibs, Alfred; Schulze, Lothar; Kreuzer, Franz Heinrich; Kolm, Hans Georg.

Reaction of 2,4-dimethyl-5-(ethoxycarbonyl)pyrrole (I) with SO2 in the presence of EtBr and AlCl3 or in CH2Cl2 containing AlCl3 gave the sulfide II or the sulfoxide III, resp. Successive reaction of SCl2 with MeOH and 2-methyl-3-(ethoxycarbonyl pyrrole gave the disulfide IV. Addition of EtSH to tris[2-methyl-3-(ethoxycarbonyl)-5-pyrrolyl]methane gave the sulfide V. Addition of p-tolysulfonyl isothiocyanate to I gave the derivative VI.

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Thiazolidine – Wikipedia,
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Related Products of 2199-44-2. 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: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Biosynthesis of porphyrins and related macrocycles. Part 25. Synthesis of analogs of coproporphyrinogen-III and studies of their interaction with coproporphyrinogen-III oxidase from Euglena gracilis. Author is Robinson, John A.; McDonald, Edward; Battersby, Alan R..

Coproporphyrinogen III analogs I [R = (CH2)3CO2H, R1 = (CH2)2CO2H; R = (CH2)2CO2H, R1 = (CH2)3CO2H, (CH2)2CO2Me; R = (CH2)2CO2Me, R1 = (CH2)2CO2H] (II-V, resp.) were prepared Coproporphyrinogen III oxidase from E. gracilis acted on III and IV, which have normal substituents on the A-ring, to generate a vinyl group on that ring. The enzyme has no effect on II and V, where the A-ring propionic acid group has been changed. The implications of this in the biosynthesis of protoporphyrinogen IX from coproporphyrinogen III are briefly discussed. Conditions have been defined for the MacDonald synthesis of porphyrins which yield products of high isomeric purity.

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Zhang, Yi; Ma, Jin Shi published the article 《Synthesis of novel tetrapyrroles and their zinc complexes》. Keywords: tetrapyrrole preparation complexation zinc; zinc tetrapyrrole complex preparation.They researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).Reference of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. 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.

2,2′-Tetramethyl-5,5′-bis(ethoxycarbonyl)-3,3′-dipyrromethane, prepared from 3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole and paraformaldehyde, was converted to the dicarboxylic acid and subsequently to the dialdehyde which was reacted with tert-butoxy 4-ethyl-3,5-dimethylpyrazole-2-carboxylate/3,4-diethyl-5-methylpyrazole-2-carboxylic acid/3,5-dimethyl-4-methoxycarbonylethylpyrrole-2-carboxylic acid to give I.2HBr (R = Me, R1 = Et or R = R1 = Et or R = Me, R1 = CH2CH2COOMe). I (R = Me, R1 = Et or CH2CH2COOMe) (HL) reacted with Zn(OAc)2 to give ZnL2.

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Reference:
Thiazolidine – Wikipedia,
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