Month: April 2022

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Chloro-7-nitro-1H-benzo[d]imidazole( cas:15965-55-6 ) is researched.Category: thiazolidine.Vivarelli, Piero; Taddei, Ferdinando published the article 《Benzimidazoles. Prototropic equilibriums and product distribution from methylation of substituted 2-chlorobenzimidazoles》 about this compound( cas:15965-55-6 ) in Gazzetta Chimica Italiana. Keywords: benzimidazole chloro methylation; methylation chlorobenzimidazole; tautomerization chlorobenzimidazole. Let’s learn more about this compound (cas:15965-55-6).

Methylation of the benzimidazoles I (R = Me, MeO, Cl, NO2, R1 = H) gave equal amounts of II and III. Methylation of I (R = H, R1 = Me, MeO, Cl, NO2) gave II and a larger amount of III. The ratio of tautomers was determined by NMR.

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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 《Synthesis of ferrocene derivatives by means of boron- and halogen-substituted ferrocenes》. Authors are Nesmeyanov, A. N.; Sazonova, V. A.; Drosd, V. N..The article about the compound:Bromoferrocenecas:1273-73-0,SMILESS:Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25).Product Details of 1273-73-0. Through the article, more information about this compound (cas:1273-73-0) is conveyed.

[R = ferrocenyl throughout this abstract] A series of new haloferrocene derivatives was prepared from RB(OH)2 (I) derivatives via RLi. Ferrocenyloxy derivatives and their esters were also synthesized and investigated. B(OBu)3 (92 g.) in Et2O was treated at -78° slowly with stirring with RLi from 17.6 g. ferrocene and BuLi (from 39 g. BuCl and 7.6 g. Li) in about 240 cc. Et2O, the mixture stirred until warmed to room temperature, kept overnight, decomposed with 10% H2SO4, the Et2O layer extracted with 10% aqueous KOH (40 cc., twice 10 cc., and five times 40 cc.). The 1st extract acidified and filtered gave 2.90 g. ferrocenylene-1,1′-diboronic acid (II), decomposed at about 180°; the 4th-8th alkali extracts gave 6.06 g. I, yellow, m. 143-8° (sealed tube); the 2nd and 3rd extracts gave a mixture of I and II which washed with Et2O left 0.44 g. II; the Et2O solution evaporated gave 0.72 g. I. I and II refluxed with aqueous ZnCl2 gave ferrocene. I (0.16 g.) in 20 cc. H2O treated with 0.19 g. HgCl2 in aqueous Me2CO gave 0.22 g. RHgCl, m. 192-4° (decomposition) (xylene). Aqueous I refluxed a few min. with excess ammoniacal Ag2O solution and extracted with Et2O, the extract evaporated, and the residue treated with petr. ether left 0.25 g. R2, m. 230-2° (decomposition) (absolute EtOH); the petr. ether solution evaporated gave 0.15 g. ferrocene. I (1 g.) in 200 cc. H2O treated at 50-60° with 1.70 g. CuCl22H2O in 50 cc. H2O, kept 15 min., steam distilled, and the product isolated from the distillate with Et2O gave 0.76 g. RCl, m. 58-9° (MeOH). In the same manner were prepared the following compounds (% yield and m.p. given): RBr, 80, 32-3°; 1,1′-dichloroferrocene (III), 75, 75-7°; 1,1′-dibromoferrocene (IV), 76, 50-1°. II (3.1 g.), 7 cc. MeOH, 4.7 g. CuCl2.2H2O, 75 cc. H2O, and 60 cc. C6H6 refluxed 2.5 h., cooled, distilled, the C6H6 layer separated, the aqueous layer added to the insoluble precipitate, diluted with 70 cc. C6H6, processed again in the same manner, saturated with NaCl, extracted with Et2O, the combined Et2O and C6H6 solutions concentrated to 50 cc., extracted with 10% aqueous KOH, and the extract acidified with 10% H2SO4 yielded 1.56 g. 1′-chloro-1-ferrocenylboronic acid (V), m. 159-61° (aqueous EtOH). Aqueous V boiled with ZnCl2 gave RCl. II and CuBr2 yielded similarly the 1′-Br analog (VI) of V, softened at about 130°, resolidified, m. 155-7°. Aqueous VI refluxed with ZnBr2 gave RBr. V (0.27 g.) in 5 cc. EtOH and 50 cc. H2O treated with 0.28 g. HgCl2 in aqueous Me2CO, the mixture heated 5 min., and filtered yielded 1′-chloro-1-ferrocenylmercuric chloride (VII), m. 144.5-45° (Me2CO), which with Na2S2O3 yielded bis(1′-chloro-1-ferrocenyl)mercury (VIIa), m. 151-2° (xylene-hexane). VI (0.30 g.) and 0.36 g. HgBr2 gave similarly 0.46 g. 1′-Br analog (VIII) of VII, m. 146.5-47° (Me2CO), which with Na2S2O3 yielded the di-Br analog of VIIa, m. 135-6° (MeNO2). VIII in xylene heated gave RBr. VII (1 g.) in 10 cc. xylene treated with 3 g. iodine in 10 cc. hot xylene, the mixture cooled, filtered, the residue washed with EtOH, shaken with 45 g. Na2S2O3 in 200 cc. H2O and with Et2O, and the Et2O layer evaporated gave 0.49 g. 1-chloro-1′-iodoferrocene, m. 42-4° (MeOH). VIII (0.80 g.) in 10 cc. xylene with 3 g. iodine in 10 cc. xylene yielded similarly 0.44 g. 1-bromo-1′-iodoferrocene, m. 28-30° (MeOH). VI (1 g) and 1.7 g. CuCl2 in 120 cc. H2O treated with steam and the product isolated from the distillate with Et2O gave 0.60 g. III, m. 75-7° (EtOH). RBr (0.60 g.) and 1.5 g. Cu phthalimide heated 2 h. at 135-40°, extracted with Et2O, and the extract worked up gave 0.48 g. N-ferrocenylphthalimide (IX), red crystals, m. 156-7° (EtOH). RCl (0.30 g.) and 1.5 g. Cu phthalimide gave similarly 0.24 g. IX. IX (0.3 g.), 0.5 cc. N2H4.H2O, and 5 cc. EtOH refluxed 40 min., diluted with H2O, extracted with Et2O, the Et2O solution extracted with 10% H2SO4, and the acidic extract basified with 10% aqueous KOH yielded 0.15 g. RNH2, m. 153-5°; N-Ac derivative m. 169-71°. RBr (0.30 g.) and 2 g. CuCN heated 2 h. at 135-40° and the product isolated with Et2O gave 0.20 g. RCN, m. 105.5-6.5°, also obtained in 42% yield from RCl and CuCN in C5H5N during 3 h. at 140-5°. RCl (2.5 g.) and 7.5 g. Cu(OAc)2 in 300 cc. 50% EtOH refluxed 15-20 min., diluted with H2O, and the product isolated with Et2O gave 2.3 g. ROAc, m. 64.5-6.5° (aqueous EtOH). RBr (0.30 g.) and 1.0 g. Cu(OAc)2 in 30 cc. 50% EtOH gave similarly 0.25 g. ROAc. I (2.5 g.) in 250 cc. hot H2O treated with 4.35 g. Cu(OAc)2 in hot H2O, the mixture cooled after 10 min., extracted with Et2O, and the residue from the extract treated with petr. ether left 0.42 g. R2, m. 230-2° (decomposition) (EtOH); the petr. ether solution evaporated gave 1.56 g. ROAc, m. 64.5-66° (EtOH). I (0.5 g.) in 60 cc. H2O and 1.0 g. Cu(O2CEt)2 in 40 cc. H2O yielded 0.30 g. EtCO2R, m. 30-1° (EtOH), and 0.08 g. R2. PhMgBr from 0.7 g. PhBr and 0.14 g. Mg in 10 cc. absolute Et2O treated under N with cooling with 0.44 g. ROAc in 5 cc. Et2O, the mixture stirred 1 h. at room temperature, decomposed with aqueous NH4Cl, and the Et2O phase worked up gave 0.23 g. MePh2COH, m. 79-81° (petr. ether); the alk. extract of the Et2O phase treated with CO2 precipitated 0.22 g. ROH, m. 166-70° (under N)(H2O). ROAc (0.40 g.), 6 cc. 10% aqueous KOH, and 8 cc. EtOH refluxed 50 min., the EtOH evaporated, the residual dark brown solution filtered, diluted to 13 cc., and treated with CO2 gave 0.29 g. ROH. VI (2 g.) in hot H2O refluxed with 5.4 g. Cu(OAc)2, cooled, and the product isolated with Et2O yielded 1.62 g. 1,1′-ferrocenylene diacetate (X), m. 55-6° (hexane). V (0.83 g.) and 2.2 g. Cu(OAc)2 gave similarly 0.66 g. X. II (2 g.) in 400 cc. hot H2O and 5.8 g. Cu(OAc)2 heated 40 min. on the water bath and the product isolated with Et2O yielded 0.90 g. X, m. 55-5.5° (hexane). IV (0.3 g.) and 1 g. Cu(OAc)2 in 30 cc. 50% EtOH refluxed 1 h., diluted with H2O, extracted with Et2O, and the extract worked up gave 0.16 g. X, m. 55.5-56° (hexane). X heated 10 min. with 20% aqueous KOH on the water bath and treated with CO2 gave 1,1′-dihydroxyferrocene (XI), yellow air-sensitive crystals, which with BzCl and alkali gave the dibenzoate. XI (from 0.80 g. X) in dry Et2O treated 1.5 h. with a stream of air, washed, and evaporated yielded 60 mg. dimeric cyclopentadienone, b8 120°, m. 96-8°. The hydrolyzates from ROAc and X treated under N with alkali, BzCl, and PhSO2Cl yielded the following compounds (% yield and m.p. given): ROBz, 85, 108.5-9.5°; ROSO2Ph, 90, 90-90.5°; dibenzoate of XI, 68, 114-15°; dibenzenesulfonate of XI, 72, 119.5-20.5°. ROAc (0.3 g.) and 0.5 cc. Me2SO4 in 5 cc. MeOH treated with 1.25 cc. 50% aqueous KOH gave 90% ROMe, m. 39.5-40.5°. X (0.20 g.) in 20 cc. MeOH treated with 3 cc. Me2SO4 yielded 95% 1,1′-dimethoxyferrocene, m. 35-6° (hexane). ROH and XI in 10% aqueous KOH refluxed 3 h. under N with 100% excess ClCH2CO2H, acidified with 10% H2SO4, and the product isolated with Et2O yielded 82% ROCH2CO2H, m. 136-7.5°, and 76% O,O’-(1,1′-ferrocenylene)diglycolic acid, m. 168.5-9.5° (H2O). ROH (0.30 g.), 1.5 g. powd. K2CO3, and 0.55 cc. CH2:CHCH2Br in 7 cc. absolute Me2CO refluxed 2 h. with stirring under N, diluted with H2O, extracted with Et2O, and the extract worked up gave 0.30 g. ROCH2CH:CH2, m. 28-30° (MeOH), which heated under N at 215-20° gave ROH.

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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 《Solubility of the quinoline and isoquinoline acid sulfates in ethyl alcohol》. Authors are Potashnikov, M. M.; Gorelov, P. N..The article about the compound:quinoliniumhydrogensulphatecas:530-66-5,SMILESS:[O-]S(=O)(O)=O.C12=CC=C[NH+]=C1C=CC=C2).Quality Control of quinoliniumhydrogensulphate. Through the article, more information about this compound (cas:530-66-5) is conveyed.

The solubility of the acid sulfates of quinoline (I) and isoquinoline (II) in 75-95% EtOH was determined for the temperature range 0-50°. The exptl. data show that crystalline hydrates are formed in ∼85% EtOH (C9H7N.H2SO4.4H2O at 0-15°; 2C9H7N.H2SO4.7H2O at 15-20°). I is 2-3 times as soluble in EtOH as is II and this fact can be used to sep. the 2 compounds

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Thiazolidine – Wikipedia,
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Product Details of 1273-73-0. 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: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Enhanced Electron-Transfer Reactivity of Nonheme Manganese(IV)-Oxo Complexes by Binding Scandium Ions. Author is Yoon, Heejung; Lee, Yong-Min; Wu, Xiujuan; Cho, Kyung-Bin; Sarangi, Ritimukta; Nam, Wonwoo; Fukuzumi, Shunichi.

One and two scandium ions (Sc3+) are bound strongly to nonheme manganese(IV)-oxo complexes, [(N4Py)MnIV(O)]2+ (N4Py = N,N-bis(2-pyridylmethyl)-N-bis(2-pyridyl)methylamine) and [(Bn-TPEN)MnIV(O)]2+ (Bn-TPEN = N-benzyl-N,N’,N’-tris(2-pyridylmethyl)-1,2-diaminoethane), to form MnIV(O)-(Sc3+)1 and MnIV(O)-(Sc3+)2 complexes, resp. The binding of Sc3+ ions to the MnIV(O) complexes was examined by spectroscopic methods as well as by DFT calculations The one-electron reduction potentials of the MnIV(O) complexes were markedly shifted to a pos. direction by binding of Sc3+ ions. Accordingly, rates of the electron transfer reactions of the MnIV(O) complexes were enhanced as much as 107-fold by binding of two Sc3+ ions. The driving force dependence of electron transfer from various electron donors to the MnIV(O) and MnIV(O)-(Sc3+)2 complexes was examined and analyzed in light of the Marcus theory of electron transfer to determine the reorganization energies of electron transfer. The smaller reorganization energies and much more pos. reduction potentials of the MnIV(O)-(Sc3+)2 complexes resulted in remarkable enhancement of the electron-transfer reactivity of the MnIV(O) complexes. Such a dramatic enhancement of the electron-transfer reactivity of the MnIV(O) complexes by binding of Sc3+ ions resulted in the change of mechanism in the sulfoxidation of thioanisoles by MnIV(O) complexes from a direct oxygen atom transfer pathway without metal ion binding to an electron-transfer pathway with binding of Sc3+ ions.

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Reference:
Thiazolidine – Wikipedia,
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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.Alberola, Angel; Andres, Jose M.; Gonzalez, Alfonso; Pedrosa, Rafael; Vicente, Martina researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.They published the article 《The reaction of β-aminoenones with α-amino derivatives. Synthesis of 2-functionalized pyrroles》 about this compound( cas:2199-44-2 ) in Heterocycles. Keywords: aminoenone transamination glycinate aminoacetonitrile; aminoalkenone preparation cyclization; pyrrole. We’ll tell you more about this compound (cas:2199-44-2).

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,
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Synthetic Route 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 Separation of carbethoxymethylpyrroles by thin-layer chromatography. Author is Roomi, M. W..

Carbethoxymethylpyrroles were separated by thin-layer chromatog. with ether-n-C6H14-2% AcOH on silica gel G. Et methylpyrrole-3-carboxylates (I, R = 2-Me, 4-Me) were separated from Et methylpyrrole-2-carboxylates (II, R = 3-Me, 5-Me) but separation of individual I (Rf = 54) and II (Rf = 70) was impossible. Et dimethylpyrrole-3-carboxylates (III, R = 4-Me, 5-Me) were separated from Et dimethylpyrrole-2-carboxylates (IV, R,R1 = 4,5-Me2, 3,5-Me2, 3,4-Me2). Individual IV were not separable (Rf = 70) but III were (Rf = 62, 54). Et trimethylpyrrole-2-carboxyl-ate (Rf = 70) was separated from Et trimethylpyrrole-3-carboxylate (Rf = 62).

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Reference:
Thiazolidine – Wikipedia,
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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: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about 1-(1′-Bromoferrocenyl)silver.Formula: C10BrFe.

Treating 0.5 g 1-bromo-1′-ferroceneboronic acid with Ag2O from 0.5 g Ag NO3 in NH4OH and heating briefly gave 53% 1-(1′-bromoferrocenyl)-silver, decomposed 125-6°. This with concentrated HCl 10 min gave 70% bromoferrocene, while pyrolysis in xylene gave a Ag mirror and 60% bis(1′-bromoferrocenyl), m. 138-40°. Treated with HgBr2 in C6H6 the Ag salt gave 80% 1-(1′-bromoferrocenyl)-mercuric bromide, m. 143-5°. The Ag derivative and BiBr3 in C6H6 in 3-4 hrs gave bromoferrocene and 50% tris(1′-bromoferrocenyl)bismuth, m. 179.5-81°. This kept in concentrated HCl 0.5 hr, then treated with aqueous NH4OH to neutrality, then percolated with H2S, gave a precipitate which was used for estimation of Bi after washing and drying to constant weight

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Reactions of haloferrocenes with organolithium compounds, the main research direction is lithium organic compound; iron organic compound; mercury organic compound; ferrocenes organolithium reagents.Application In Synthesis of Bromoferrocene.

Reactions of BuLi or PhLi with chloroferrocene (I), 1,1′-dichloroferrocene (II), and bromoferrocene (III) were investigated. I (0.802 g) in 25 ml Et2O treated with 200 millimoles. BuLi in Et2O and quenched with H2O gave 0.033 g ferrocene (IV) and 0.534 g I. Lithiation of 0.870 g I followed by carbonation and esterification afforded 0.398 g Me 2-chloroferrocenecarboxylate (V) and 0.051 g di-Me 2-chloroferrocene-1,1′-dicarboxylate. Similarly I and PhLi gave 21% V. Heating I and PhLi 4.5 hr and quenching with H2O afforded 50% I, 8% IV, and 24% phenylferrocene (V). However no ferrocyne was detected in attempted capture with some dienes. Similarly lithiation of II followed by carbonation and esterification gave meso and racemic forms, m. 117-17.5° and 110-11°, of di-Me 2,2′-dichloroferrocenedicarboxylates in 48% yield. The reaction of III with BuLi at -78° followed by quenching with H2O gave 36% IV and 37% IV, whereas lithiation at room temperature gave 99% IV. Treating III with PhLi also afforded small amount of V. Lithiation at the 2-position is favored in the case of the Cl compound whereas Br-Li exchange is favored in the case of the Br compound I lithiated with BuLi and treated with HgBr2 gave bis(2-chloroferrocenyl)mercury (VI), m. 219-20°. Similarly bis(2,1′-dichloroferrocenyl)mercury was prepared Attempted capture of ferrocyne by heating VI in tetracyclone ended in failure, the product being IV.

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Product Details of 2199-44-2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Electrophilic substitution of pyrroles with acyl chlorides. Author is Treibs, Alfred; Kreuzer, Franz H..

Pyrrole derivatives are readily substituted in the α and β positions by oxalyl chloride to give glyoxylic acid derivatives In the same way, pyrroles are substituted by trichloroacetyl chloride, in the absence of a catalyst, to give 2-trichloroacetylpyrroles, which afford pyrrolecarboxylic acids on treatment with alkali.

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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 Photophysical properties of a C6 hydrocarbon-linked porphyrin dimer.Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

The porphyrin dimer I and its Zn complex were prepared Fluorescence quantum yields and excited singlet and triplet state lifetimes, recorded for the dimers and the corresponding monomer species, suggest that the dimeric porphyrins exist in solution in both open and closed conformations. The open conformations retain photophys. properties similar to those of the monomerics but the closed conformations do not fluoresce.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com