784-98-5Relevant academic research and scientific papers
A new and efficient method for the synthesis of 3-(2-nitrophenyl)pyruvic acid derivatives and indoles based on the Reissert reaction
Mamedov, Vakhid A.,Mamedova, Vera L.,Syakaev, Victor V.,Khikmatova, Gul'naz Z.,Korshin, Dmitry E.,Kushatov, Temur A.,Latypov, Shamil K.
, p. 3923 - 3925 (2018/10/02)
The formation of 3-(2-nitrophenyl)pyruvic acid and its amide and ester derivatives – key compounds for the Reissert indole synthesis – was achieved under various reaction conditions via the acid catalyzed hydrolysis of 5-(2-nitrobenzyliden)-2,2-dimethyl-1,3-oxazolidin-4-one, which is readily available from 3-(2-nitrophenyl)oxirane-2-carboxamide. A new and highly efficient method for the synthesis of indole-2-carboxylic acid derivatives via the intramolecular reductive cyclization of o-nitrophenylpyruvic acid and its amide and ester derivatives was developed using Na2S2O4 in dioxane/water at reflux.
Reductive acid-catalyzed rearrangement of 3-(2-nitrobenzyl)quinoxalin-2(1Н)-ones in the presence of Na2S2O4 – effective method for the synthesis of 2-(indol-2-yl)benzimidazoles
Mamedov, Vakhid A.,Khafizova, Elena A.,Syakaev, Victor V.,Bazanova, Olga B.,Zamaletdinova, Anastasiya I.,Rizvanov, Il’dar Kh.,Latypov, Shamil K.,Sinyashin, Oleg G.
, p. 1033 - 1044 (2017/11/16)
[Figure not available: see fulltext.] An effective one-step method is proposed for the synthesis of 2-(indol-2-yl)benzimidazoles from 3-(2-nitrobenzyl)quinoxalin-2(1Н)-ones without using metal catalysts and reagents. This method is based on the Mamedov rearrangement of 3-(2-aminobenzyl)quinoxalin-2(1Н)-ones, formed in situ by the action of Na2S2O4, giving 2-(indol-2-yl)benzimidazoles as the products.
A Pd/C reduction method adopting water as a solvent for preparing indole-2-carboxylic acid
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Paragraph 0009; 0011; 0013; 0015, (2017/04/26)
The invention relates to a Pd/C reduction method adopting water as a solvent for preparing indole-2-carboxylic acid. Ethyl 2-nitrophenyl pyruvate is subjected to hydrogenation reduction cyclization in a high-pressure reaction kettle by adopting water as the solvent and adopting Pd/C as a catalyst, the Pd/C is recovered by filtering, and a filtrate is subjected to distillation, acidity adjustment and crystallization to obtain the indole-2-carboxylic acid. The catalyst is easily available and low in cost and can be repeatedly used. According to the method, the raw material can be easily recovered, post-treatment operation is simple, environment pollution is low, reaction operation safety is high, a reaction yield is high, and product quality is good, thus facilitating industrialization.
Synthetic method of indole-2-formic acid
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Paragraph 0027; 0028, (2016/10/17)
The invention discloses a synthetic method of indole-2-formic acid. According to the synthetic method, o-nitrotoluene and diethyl oxalate are used as raw materials; after an o-nitrotoluene pyruvic acid ethyl acetate solution is prepared, a silver chloride-manganese dioxide-titanium dioxide-calcium carbonate mixed catalyst is added under an alkaline condition, and is used for catalyzing to synthesize the indole-2-formic acid. The invention further discloses components of a mixed catalyst and a preparation method: calcium carbonate is used as a carrier, and silver chloride and manganese dioxide are used as active components, wherein the silver chloride accounts for 12 percent to 17 percent of the total mass of the catalyst, the manganese dioxide accounts for 5 percent to 9 percent of the total mass of the catalyst, titanium dioxide accounts for 1 percent to 2.5 percent of the total mass of the catalyst, and the balance is the calcium carbonate; the synthetic method belongs to the field of organic synthetic chemistry. The indole-2-formic acid is synthesized by adopting a mixed catalyst catalytic hydrogenation reaction; the raw materials of the catalyst are easy to obtain and the preparation method is simple and convenient; meanwhile, the catalytic efficiency is high and the yield of the indole-2-formic acid is high; the synthetic method is efficient and environmentally friendly and has extremely high economic benefits, and industrialized popularization is facilitated.
Methylglucoside phenylpyruvic acid Antidiabetes enolic type (by machine translation)
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Paragraph 0071, (2016/10/31)
PROBLEM TO BE SOLVED: pharmaceutical, especially sugar normal agent, in other words, for antiobestic, before the diabetes, or diabetes, Antiobesic and/or of a mammal having X syndrome sugar is lowered to a normal value to be used as a medicine, phenylpyruvic acid and its derivatives methylglucoside antidiabetes enolic type. SOLUTION: the compound of the present invention, useful for managing hypoglycaemia, in other words, by balancing hypoglycaemia physical condition; a balanced sugar, especially of human diabete balanced helps keep the blood sugar level; by sthenia gulucose taken by cells, by lowering the value of sugar helps and, hence, to improve the recovery or tolerance; optimizing a sugar response; tolerance. Selected drawing: no (by machine translation)
SYNTHESIS OF INDOLES FROM ACETOACETIC ESTERS
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, (2021/05/29)
The present invention relates to a synthesizing method of indole using acetoacetic ester and, more specifically, to a synthesizing method of indole which induces reduction of a nitro group into an amine group and aromatic cyclization with a ketone group through hydrogenation using a metal catalyst in a 2-nitrobenzyl ketone compound, after synthesizing the 2-nitrobenzyl ketone compound through deacetylation using a manganese (III) / cobalt (II) catalyst in a 2-nitrobenzyl acetone compound obtained by adding an acetoacetic ester compound in a 2-nitrobenzyl bromide compound.COPYRIGHT KIPO 2016
Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations
Ju, Yeming,Miao, Di,Yu, Ruiyang,Koo, Sangho
, p. 2588 - 2599 (2015/04/21)
One pot syntheses of furan, thiophene, and pyrrole were accomplished by oxidative deacetylation using Mn(iii)/Co(ii) catalysts and the Paal-Knorr reaction from 1,5-dicarbonyl compounds, which are prepared from the conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds. The oxidative deacetylation and reductive cyclization of β-ketoesters derived from ethyl acetoacetate and o-nitrobenzyl bromides efficiently produced diversely substituted indoles. This journal is
Preparation of optically enriched 3-hydroxy-3,4-dihydroquinolin-2(1H)-ones by heterogeneous catalytic cascade reaction over supported platinum catalyst
Szollosi, Gyoergy,Makra, Zsolt,Kovacs, Lenke,Fueloep, Ferenc,Bartok, Mihaly
, p. 1623 - 1629 (2013/07/04)
The development of a novel heterogeneous catalytic asymmetric cascade reaction for the synthesis of tetrahydroquinolines from 2-nitrophenylpyruvates is reported. Optically enriched 3-hydroxy-3,4-dihydroquinolin-2(1H)-ones are prepared by enantioselective hydrogenation of the activated keto group over a Cinchona alkaloid-modified Pt catalyst, reduction of the nitro group and spontaneous cyclization cascade. Acceleration of the enantioselective hydrogenation of the activated keto group over the catalyst modified by Cinchona alkaloids ensured high tetrahydroquinolinone selectivities. The scope of the reaction was checked using twelve substrates. Both yields and enantioselectivities were significantly influenced by the nature and position of the substituents on the phenyl ring. Substituents adjacent to the nitro group considerably increased the product yield, due to their effect on the nitro group′s reduction rate; however, had only a limited effect on enantioselectivities. Copyright
Asymmetric 1,3-dipolar cycloadditions of 2-diazocyclohexane-1,3-diones and alkyl diazopyruvates
Mueller, Paul,Chappellet, Sabrina
, p. 1010 - 1021 (2007/10/03)
The 1,3-dipolar cycloaddition reactions of 2-diazocyclohexane-1,3-dione (7a; Table 1) and of alkyl diazopyruvates (11a-e; Table 3) to 2,3-dihydrofuran and other enol ethers have been investigated in the presence of chiral transition metal catalysts. With RhII catalysts, the cycloadditions were not enantioselective, but those catalyzed by [RuIICl 2(1a)] and [RuIICl2(1b)] proceeded with enantioselectivities of up to 58% and 74% ee, respectively, when diazopyruvates 11 were used as substrates. The phenyliodonium ylide 7c yielded the adduct 8a in lower yield and poorer selectivity than the corresponding diazo precursor 7a (Table2) upon decomposition with [Ru(pybox)] catalysts. This suggests that ylide decomposition by RuII catalysts, contrary to that of the corresponding diazo precursors, does not lead to Ru-carbene complexes as reactive intermediates. Our method represents the first reproducible, enantioselective 1,3-cycloaddition of these types of substrates.
Unexpected formation of quinolone derivatives in Reissert indole synthesis
Suzuki,Gyoutoku,Yokoo,Shinba,Sato,Yamada,Murakami
, p. 1196 - 1198 (2007/10/03)
The Reissert indole synthesis was found to unexpectedly give 3-hydroxy-1,2,3,4-tetrahydro-2-quinolone derivative 4, sometimes in a high ratio with the expected ethyl indole-2-carboxylate derivatives 3 in a low ratio, depending on the conditions of the catalytic reduction of the intermediate 2-nitrophenylpyruvate 2. This reactivity is characteristic in the preparation of 7-substituted indoles.
