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 《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,
Thiazolidine – ScienceDirect.com

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 Synthesis and properties of (1,2,3,7,9-pentamethyldipyrrolylmethen-8-yl)-(1,2,3,7,8-pentamethyldipyrrolylmethen-9-yl)methane and bis(1,2,3,7,9-pentamethyldipyrrolylmethen-8-yl)trifluoromethylmethane dihydrobromides, the main research direction is bisdipyrrolylmethene preparation UVvis thermal oxidative degradation.Application In Synthesis of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

(1,2,3,7,9-Pentamethyldipyrrolylmethen-8-yl)(1,2,3,7,8-pentamethyldipyrrolylmethen-9-yl)-methane and bis(1,2,3,7,9-pentamethyldipyrrolylmethen-8-yl)trifluoromethylmethane hydrobromides were synthesized and characterized spectrally (1H NMR, IR, electron absorption spectra). A comparative study was performed of the effect of the bonding site (α- or β-position of the dipyrrolylmethene) with the methane structural fragment connecting two dipyrrolylmethene chromophores, and trifluoromethyl group on the spectral properties of the mols. of compounds dissolved in organic solvents of different nature and their resistance to thermal oxidative degradation

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

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 Synthetic sympatholytic substances in the ergotamine series. V. Some derivatives of 1,2,3,4-tetrahydroquinoline, published in 1952, which mentions a compound: 114527-53-6, mainly applied to , Safety of 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid.

cf. C.A. 46, 5602g. In connection with investigations aimed at establishing the relations between the chem. structure and biol. activity of compounds of the type of the alkaloids of Segale cornuta, it seemed of interest to study some 3-substituted derivatives of 1,2,3,4-tetrahydroquinoline (I), particularly since the structure of I is found in the lysergic acid mol. By a modification of the method of Gilman and Spatz (C.A. 35, 5495.2), 83 g. 3-quinolinecarboxylic acid (II), m. 275-6°, was obtained by refluxing 108 g. 3-cyanoquinoline (III) and 20% aqueous NaOH 2 hrs. The Na salt of II (25 g.) in 200 cc. water and 5 g. Raney Ni, hydrogenated 2 hrs. at 150° and 120 atm., filtered, the filtrate concentrated, acidified with HCl (d. 1.17) (to Congo red), and the precipitate purified by dilute EtOH yield 14 g. 1,2,3,4-tetrahydro-3-quinolinecarboxylic acid-HCl (IV), m. 236°, which with NH4OH yields the free acid, m. 145-6° (from EtOH). IV (0.2 g.) in 3 cc. anhydrous C5H5N and 1.6 g. Ac2O, refluxed 10 min., poured when cool into 10 cc. water + 6 cc. HCl, allowed to stand, and the precipitate purified by EtOH, yield the 1-Ac derivative, C12H14O2N, straw-colored, m. 152°. A suspension of 100 g. III in 1400 cc. MeOH refluxed 10 hrs. in a current of HCl gas (III.HCl forms first), most of the MeOH distilled, the residue poured into 3 l. ice-water, made alk. with K2CO3, kept ice-cold several hrs., and the precipitate purified by MeOH, yields 82 g. of Me 3-quinolinecarboxylate (V), m. 73-4°. V (36 g.) in 300 cc. MeOH with 5 g. Pd-C, hydrogenated at 60-65° under 90 atm., filtered, concentrated in vacuo, and allowed to stand, yields Me dihydro-3-quinolinecarboxylate (VI), m. 134-5°, is strongly fluorescent in Wood light (both solid and in solution), reduces neutral AgNO3 solution, is oxidized by dilute KMnO4; picrate, m. 187-9°. V (2 g.) in 50 cc. MeOH with 2 g. Raney Ni, hydrogenated 3 hrs. at 110° under 100 atm., filtered, and distilled at 115° (0.1 mm.); or 5 g. VI in 100 cc. MeOH with 4 g. Raney Ni and 1 g. 10% Pd-C, hydrogenated at 100° under 100 atm., and the product filtered, concentrated, and distilled in vacuo, yields the 1,2,3,4-tetrahydro derivative (VII), of VI, viscous oil, b0.3 124°. With HCl, it forms an HCl salt, m. 181-4°, and with picric acid a picrate, m. 151-3°. VII (1 g.) and 5-8 cc. concentrated HCl, heated in a sealed tube 3 hrs. at 100°, and the product purified by dilute EtOH, yield 1,2,3,4-tetrahydro-3-quinolinecarboxylic acid-HCl (VIII), m. 234°. N,N-Diethyl-3-quinolinecarboxamide (IX) (10 g.) in 100 cc. MeOH with 3 g. 10% Pd-C, hydrogenated 3 hrs. at 60° under 90 atm., filtered, concentrated, and the precipitate purified by EtOH, yields 1,2,3,4-tetrahydro derivative (X), m. 132-3°, forming with HCl a HCl salt, m. 160-1°. Hydrolyzed like VII, X yields VIII, m. 235-6°. 3-Aminoquinoline (XI) (144 g.) in 400 cc. tetrahydronaphthalene with 15 g. Raney Ni, hydrogenated at 55° under 90 atm., filtered, distilled in vacuo, and the residue rectified in vacuo, yields 127 g. crude product, b8 160-6°, which, fractionated and the fractions b. above 164° distilled in vacuo (0.8 mm.) at 250°, yields the 1,2,3,4-tetrahydro derivative (XII), m. 57°; picrate (from anhydrous EtOH), m. 205-6°; HCl salt (from EtOH by addition of Et2O), sinters 240°, m. 250°, turns violet by oxidation in air. XII oxidizes easily on exposure to air and light, and shows triboluminescence when rubbed with a wooden spatula. Benzoylated by the Schotten-Bauman method, XII gives a di-Bz derivative, C23H20O2N2, m. 201° (from EtOH). The distillation residue of XII (a fraction, b0.8 250°), fractionated further, gives a fraction, b0.4 234°, 3,3′-iminobis(1,2,3,4-tetrahydroquinoline) (XIII), very viscous resinous oil. With HCl, it forms a HCl salt (XIV), m. 254°, and with picric acid a picrate, m. 190-2°. In aqueous HCl solution, XIV gives with aqueous NaNO2 a yellow precipitate, which, purified by EtOH, yields the nitroso derivative, C18H18O3N6, m. 156°. Et2SO4 (9 cc.), added during 1 hr. to 15 g. XII in 200 cc. anhydrous Me2CO and 16 g. K2CO3, the mixture refluxed 6 hrs., filtered, evaporated, excess 20% aqueous NaOH added, the solution extracted with Et2O, the extract dried by K2CO3, evaporated, and the residue distilled in vacuo, yields 3-ethylamino-1,2,3,4-tetrahydroquinoline, b0.1 110-13°; picrate (from anhydrous EtOH), m. 198°. Et2SO4 (28 cc.), added during 1 hr. to 15 g. XII in 300 cc. anhydrous Me2CO and 48 g. K2CO3, the mixture refluxed 8 hrs., and the foregoing procedure followed, yields 3-diethylamino-1-ethyl-1,2,3,4-tetrahydroquinoline, b0.4 116°; picrate, m. 103-4°; HCl salt, very hygroscopic. The ultraviolet absorption spectra of II, IV, V, VI, VII, IX, X, XI, and XII are reproduced.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Electric Literature of C9H13NO2. 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 Synthesis and spectral properties of helicate of cobalt(II) with Bis(1,2,3,7,9-pentamethyldipyrrolylmethen-3-yl)methane. Author is Antina, L. A.; Dudina, N. A.; Berezin, M. B.; Guseva, G. B..

Ligand bis(1,2,3,7,9-pentamethyldipyrrolylmethen-8-yl)methane (H2L) was synthesized as a hydrobromide salt (H2L·2HBr) (1). Reaction of cobalt(II) acetate tetrahydrate with compound (1) in a chloroform/methanol mixture in the presence of triethylamine afforded a binuclear homoleptic double-helical complex [Co2(L)2] (2). UV absorption, 13C and 1H NMR spectra were used to characterize the compounds 1 and 2.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 2199-44-2, is researched, SMILESS is O=C(C1=C(C)C=C(C)N1)OCC, Molecular C9H13NO2Journal, Zhurnal Obshchei Khimii called Synthesis of higher aliphatic pyrrolyl ketones, Author is Zhestkov, V. P.; Mironov, A. F.; Evstigneeva, R. P., the main research direction is ketone pyrrole nonyl; decanone pyrrolyl.HPLC of Formula: 2199-44-2.

Alkylation of Et 3,5-dimethylpyrrole-2-carboxylate (I; R = CO2Et, R1 = H) by MeO2CCH2COCl in MeNO2 containing SnCl4 gave 65% pyrrole-3-propionate (I; R = CO2Et, R1 = COCH2CO2Me) which was alkylated by octyl bromide to give I [R = CO2Et, R1 = COCH(CO2Me)(CH2)7Me]. Subsequent decarboxylation at 200° gave 44% 2,4-dimethyl-3-(1-oxodecyl)pyrrole [I; R = H, R1 = CO(CH2)8Me].

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Mothana, B.; Ban, F.; Boyd, R. J.; Thompson, A.; Hadden, C. E. 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 ).Quality Control 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.

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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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Safety 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 Complexation between decamethyl-3,3′-bis(dipyrrolylmethene) and zinc(II), copper(II), and cobalt(II) acetates. Author is Guseva, G. B.; Dudina, N. A.; Antina, E. V.; V’yugin, A. I.; Semeikin, A. S..

Decamethylmethylene-3,3′-bis(dipyrrolylmethene) dihydrobromide H2L·2HBr, which is the simplest representative of a novel class of oligo(dipyrrolylmethenes) belonging to chromophore chelating nonmacrocyclic ligands, were examined by 1H NMR, IR, and electronic absorption spectroscopy. Complexation reactions of H2L·2HBr with M(AcO)2 (M = Zn(II), Cu(II), and Co(II)) in DMF at 298.15 K were monitored by electronic absorption spectroscopy and studied by the molar ratio method. The thermodn. constants K0 of these reactions were estimated The d metal ions coordinate H2L to give the binuclear homoleptic complexes [M2L2]. The reactions proceed through the intermediate binuclear heteroleptic complex [M2L(AcO)2] detected by spectroscopic methods. The thermodn. stabilities of [M2L2] and [M2L(AcO)2] increase when moving from Cu(II) to Zn(II) and Co(II). The probability of formation and stability of [M2L2] containing 3,3′-bis(dipyrrolylmethene) are substantially higher than those of analogous complexes with the 2,2′-isomer (decamethyl-2,2′-biladiene-a,c). The low K0 values for the complexation between H2L and Cu(AcO)2 are due to slow oxidation of the biladiene ligand into a bilatriene with participation of Cu2+ ions.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Skowronek, Pawel; Lightner, David A. published the article 《Synthesis of a chiral 3,3′-di-tert-butyl-2,2′-bipyrrole》. Keywords: chiral bipyrroledicarboxylate derivative preparation x ray; crystal structure chiral bipyrroledicarboxylate derivative; mol structure chiral bipyrroledicarboxylate derivative; atropisomer bipyrroledicarboxylate derivative preparation x ray.They researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).Recommanded Product: 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.

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,
Thiazolidine – ScienceDirect.com

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.Boiadjiev, Stefan E.; Lightner, David A. researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).Application In Synthesis of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.They published the article 《Atropisomerism in monopyrroles》 about this compound( cas:2199-44-2 ) in Tetrahedron: Asymmetry. Keywords: dynamic NMR atropisomerism monopyrrole rotation barrier kinetics. We’ll tell you more about this compound (cas:2199-44-2).

As observed by NMR, iodopyrroles 1a and 1b (Et and Me 3,5-dimethyl-4-[(1′-iodo-2′,2′-dimethyl)propyl]pyrrole-2-carboxylate) and a variety of related derivatives with iodine replaced by methoxy 2, thiomethyl 3, acetic acid esters 4, propionic acid ester 5 or malonic esters 6 exhibit restricted rotation about the C(4)-C(1′) bond due to the bulky tert-Bu group and an ortho effect from the sterically crowded 3,5-dimethylpyrrole. Most of the compounds, which are members of the rare class of atropisomers due to restricted rotation about an sp3-sp2 C-C bond, undergo diastereomeric enrichment by preparative TLC and crystallization From dynamic NMR studies of the enriched diastereomers one can determine kinetic and thermodn. parameters associated with the atropisomerism, e.g., ΔG‡ ∼24 kcal/mol for 1 and 5 (313 K), ∼22 kcal/mol for 3 (273 K), and ∼25 kcal/mol for 6 (313 K) in C2D2Cl4 solvent.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

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

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,
Thiazolidine – ScienceDirect.com