Month: April 2022

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 Complexation between decamethyl-3,3′-bis(dipyrrolylmethene) and zinc(II), copper(II), and cobalt(II) acetates, published in 2009-01-31, which mentions a compound: 2199-44-2, Name is Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, Molecular C9H13NO2, Reference of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

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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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Halogen compounds of ferrocene》. Authors are Nesmeyanov, A. N.; Perevalova, E. G.; Nesmeyanova, O. A..The article about the compound:Bromoferrocenecas:1273-73-0,SMILESS:Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25).Formula: C10BrFe. Through the article, more information about this compound (cas:1273-73-0) is conveyed.

Iodine and ferrocene in organic medium yields a complex containing 20 atoms of iodine per mole of ferrocene, a black solid with green luster, decompose 170-2°; crystallization from Me2CO yields a complex with 6 atoms of iodine per mol., black, decompose 125-30°. The former complex in H2O yields the ferricinium cation color, while the latter complex is unattacked by H2O. Na2S2O3 removes iodine, from the complexes. Br and ferrocene give a brown complex, which is flammable when dry. Heating ferrocene with Br in CCl4 yields pentabromocyclopentane, m. 103-4°; Cl decomposes ferrocene at room temperature but at -30° in CHCl3 it yields a complex with 26% Cl. Ferrocenylmercury chloride in hot xylene treated with iodine gave a green precipitate of a complex of ferrocenylmercury chloride with 4 atoms of iodine; aqueous Na2S2O3 converts this to bisferrocenylmercury. Much iodine converts the complex and replaces Hg by iodine and the precipitate turns black, yielding 64% iodoferrocene after treatment with Na2S2O3. Iodoferrocene is yellow-orange, m. 44-5°, is volatile with steam and can be crystallized from MeOH at -10°. Its iodine is inert; heated to 100° it yields ferrocene and some C; it fails to form RMgI with Mg. Bisferrocenylmercury with excess Br in CHCl3 gave after 0.5 hr. refluxing, followed by treatment with Na2S2O3, a low yield of bromoferrocene, yellow, m. 30-1° (from MeOH). Treatment of bis(chloromercury)ferrocene with I or Br gave the corresponding diiodo- and dibromoferrocenes. The former, 25%, was not pure even after chromatographic purification; it was a red liquid, d20 2.286, d36 2.262, nD26 1.682. Dibromoferrocene, red liquid, absorption maximum 438 mμ. Bromoferrocene has an absolute maximum at 437; diiodoferrocene 438; iodoferrocene 435 mμ.

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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 Synthesis of cyanopyrroles, published in 1999-01-31, which mentions a compound: 2199-44-2, mainly applied to cyanopyrrole preparation; pyrrolenitrile preparation; oximinocyanoacetate diketone Knorr reductive condensation, Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

Regioselective synthesis of α-cyanopyrroles (vs. α-alkoxycarbonylpyrroles) using oximinocyanoacetate esters in a Knorr-type reductive condensation with β-diketones can be directed by the presence of water. Thus, HON:C(CN)CO2Me was reacted with CH2Ac2 in hot AcOH in the presence of Zn dust to give exclusively 3,5-dimethylpyrrole-2-carbonitrile when the AcOH was wet. Whereas, in glacial AcOH, only Me 3,5-dimethylpyrrole-2-carboxylate was isolated in ∼40% yield.

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Electric Literature of C13H15F3N2O. 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: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, is researched, Molecular C13H15F3N2O, CAS is 1428537-19-2, about Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes.

Transition-metal-catalyzed dicarbofunctionalization of alkenes involving intramol. Heck cyclization followed by intermol. cross-coupling has emerged as a powerful engine for building heterocycles with sterically congested quaternary carbon centers. However, only exo-cyclization/cross-coupling products can be obtained; endo-selective cyclization/cross-coupling has not been reported yet and still poses a formidable challenge. We herein report the first example of catalyst-controlled dicarbofunctionalization of alkenes for the regiodivergent synthesis of five- and six-membered benzo-fused lactams bearing all-carbon quaternary centers. Using a chiral Pyrox- or Phox-type bidentate ligand, 5-exo cyclization/cross-couplings proceed favorably to produce indole-2-ones in good yields with excellent regioselectivity and enantioselectivities (up to 98% ee). When C6-carboxylic acid-modified 2,2′-bipyridine was used as the ligand, 3,4-dihydroquinolin-2-ones were obtained in good yields through 6-endo-selective cyclization/cross-coupling processes. This transformation is modular and tolerant of a variety of functional groups. The ligand rather than the substrate structures precisely dictates the regioselectivity pattern. Moreover, the synthetic value of this regiodivergent protocol was demonstrated by the preparation of biol. relevant mols. and structural scaffolds.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some reactions of halogen derivatives of ferrocene. Ferrocenylamine. Ferrocenyl acetate》. Authors are Nesmeyanov, A. N.; Sazonova, V. A.; Drozd, 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).Name: Bromoferrocene. Through the article, more information about this compound (cas:1273-73-0) is conveyed.

cf. C.A. 50, 2558a; 54, 6673h. Refluxing 0.3 g. bromoferrocene (I) with 1 g. Cu(OAc)2 in 30 ml. 50% EtOH 15 min. gave 90% ferrocenyl acetate, m. 64.5-6.5° (EtOH); hydrolysis and treatment with BzCl gave ferrocenyl benzoate, m. 108.5-9.5°. Ferrocenyl acetate was similarly prepared in 84% yield from chloroferrocene. Heating 0.6 g. I with 1.5 g. Cu phthalimide 2 hrs. at 135-40° gave after extraction with Et2O 64% N-ferrocenylphthalimide, m. 156-7° (EtOH); chloroferrocene gave a 53% yield. Refluxing the imide with N2H4.H2O in EtOH under N 40 min. gave after an aqueous treatment 82% ferrocenylamine, m. 153-5°, which with Ac2O in pyridine at room temperature gave 82% N-acetylferrocenylamine, m. 169-71°. Heating I with Cu(CN)2 2 hrs. at 140° gave 84% ferrocenecarbonitrile, m. 105.5-6.5°; the yield was 42% when the reaction was run 3 hrs. in pyridine with chloroferrocene and when a small amount of the nitrile was originally present in the reaction mixture

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HPLC of Formula: 530-66-5. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: quinoliniumhydrogensulphate, is researched, Molecular C9H9NO4S, CAS is 530-66-5, about Quenching of the luminescence in complexes with hydrogen bonding Model systems of aromatic hydrocarbons-nitrogenous heterocycle salts. Author is Krasheninnikov, A. A..

Luminescence quenching constants for systems containing acid salts of heterocyclic bases (pyridine, quinoline, acridine) and aromatic hydrocarbons (phenanthrene, anthracene, naphthacene) indicated that charge-transfer complex formation occurred and that quenching resulted from electron transfer from the aromatic hydrocarbon to the heterocyclic cation.

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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).Safety of Bromoferrocene. 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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Luebbe, Claus; Van Pee, Karl Heinz; Salcher, Olga; Lingens, Franz published an article about the compound: 2-(7-Bromo-1H-indol-3-yl)acetic acid( cas:63352-97-6,SMILESS:O=C(O)CC1=CNC2=C1C=CC=C2Br ).Recommanded Product: 2-(7-Bromo-1H-indol-3-yl)acetic acid. 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:63352-97-6) through the article.

P. pyrrocinia ATCC 15958 and a mutant strain (ACN) of P. aureofaciens ATCC 15926 possess a mechanism for the degradation of the tryptophan side chain. Indole, indole-3-carboxylic acid, indole-3-acetic acid, the corresponding compounds chlorinated or brominated at position 7, indole-3-pyruvate, and 7-chloroindole-3-pyruvate were isolated from bacterial cultures. The chlorinated indole derivatives were isolated after the addition of 7-chloro-DL-tryptophan to cultures of P. pyrrocinia whereas their bromo analogs were found in the culture medium of the mutant strain ACN of P. aureofaciens, grown in the presence of NaBr. Enzymic studies show that tryptophan is transaminated to indole-3-pyruvate, which is transformed to indole-3-acetaldehyde. Dehydrogenation of indole-3-acetaldehyde leads to indole-3-acetic acid, which is further metabolized to indole-3-carboxaldehyde and converted by dehydrogenation to indole-3-carboxylic acid. Indole is formed by the spontaneous decarboxylation of indole-3-carboxylic acid.

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Product Details of 1273-73-0. 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: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about Dye regeneration and charge recombination in dye-sensitized solar cells with ferrocene derivatives as redox mediators. Author is Daeneke, Torben; Mozer, Attila J.; Kwon, Tae-Hyuk; Duffy, Noel W.; Holmes, Andrew B.; Bach, Udo; Spiccia, Leone.

Ferrocene compounds are promising redox shuttles for application in dye-sensitized solar cells (DSCs). Chem. modification of the cyclopentadienyl rings is easily achievable affording almost unlimited variation of the redox properties. This allows fine-tuning of the driving force for dye-regeneration and optimization of the energy conversion efficiency of DSCs. Herein, six ferrocene derivatives have been chosen for investigation which cover the large redox potential range of 0.85 V, by virtue of simple alkylation and halogenation of the cyclopentadienyl ring, and enable improved matching of the energy levels of the sensitizer and the electrolyte. Although the focus of this work was to examine the effect of the redox potential on charge transfer processes, DSCs were fabricated which achieved high energy conversion efficiencies of over 5%. Charge transfer reactions were studied to reveal the dependence of the dye regeneration rate, recombination losses and recombination pathways on the reaction driving force. An increase in redox potential led to a higher efficiency due to higher open circuit potentials until a threshold is reached. At this threshold, the driving force for dye regeneration (18 kJ mol-1, ΔE = 0.19 V) becomes too small for efficient device operation, leading to rapid recombination between the oxidized dye and electrons in the TiO2 conduction band. As a result of this work guidelines can be formulated to aid the selection of redox couples for a particular sensitizer in order to maximize the utilization of incident solar energy.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《A new pyrrole synthesis》. Authors are Fischer, Hans; Fink, Emmy.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.

Mutual reduction of isonitrosoacetoacetic ester or isonitrosobutyryl-acetic ester and AcCH2CH(OEt)2 (I) in the presence of Zn dust yielded 2-methyl-5-carbethoxypyrrole (II), m. 100°, subliming at 90° at 20 mm. On treatment with HCN and HCl in ether, II was converted to 2-methyl-5-carbethoxy-3-pyrrolecarboxaldehyde, m. 119°. I, heated with glacial AcOH for 1/2 h., yielded triacetylbenzene (III), m. 161°. In cold glacial AcOH, III was formed in only minimal amounts from I, but in considerable amounts from the Na salt of formylacetone. Acetylacetone was condensed with isonitrosoacetoacetic ester to form 2,4-dimethyl-3-acetyl-5-carbethoxypyrrole, and as a side-product, 2,4-dimethyl-5-carbethoxypyrrole, m. 123°. Glycine was condensed with AcCH2CHO, or with I, or with the Na salt of formylacetone, to yield a product, not yet isolated, giving a pos. Ehrlich reaction for pyrrole. These syntheses may be of physiol. importance in the formation of blood pigments.

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