20973-67-5Relevant academic research and scientific papers
CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence
Ye, Yuxuan,Kim, Seoung-Tae,Jeong, Jinhoon,Baik, Mu-Hyun,Buchwald, Stephen L.
, p. 3901 - 3909 (2019)
Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)indoles, as coupling partners. N- or C3-alkylated indoles are prepared with high levels of regio- and enantioselectivity using a copper hydride catalyst. The regioselectivity is governed by the use of either DTBM-SEGPHOS or Ph-BPE as the supporting ligand. Density functional theory (DFT) calculations are conducted to elucidate the origin of the ligand-controlled regiodivergence.
Synthesis and anti-inflammatory activity of indole glucosinolates
Vo, Quan V.,Trenerry, Craige,Rochfort, Simone,Wadeson, Jenny,Leyton, Carolina,Hughes, Andrew B.
, p. 856 - 864 (2014)
The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassici
TFA-catalysed tandem double cyclisation: A one-pot, metal-free routes for novel indolo-imidazo[1,2-a]pyridine derivatives
Ganesher, Asha,Panda, Gautam
supporting information, (2019/11/11)
A transition-metal free, one-pot tandem synthetic routes for novel indole and imidazo[1,2-a]pyridine derivative hybrids have been established. An efficient three-component reaction was designed with incorporation of two sequential Groebke–Blackburn–Bienay
Synthetic process of aromatic acetaldehyde compound
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Paragraph 0063; 0064; 0065; 0066, (2017/11/30)
The invention provides a synthetic process of an aromatic acetaldehyde compound; the synthetic method includes forming a mixed solution via starting material A with N,N-dimethylformamide dimethyl acetal; continuously feeding the mixed solution into a continuous reactor to carry out enamination reaction to obtain enamide B, and discharging the enamide B from the continuous reactor during enamination reaction; preparing aromatic acetaldehyde compound C with the enamide B, wherein the starting material A has a structural formula shown as formula (1), the enamide B has a structural formula shown as formula (2), and the aromatic acetaldehyde compound C has a structural formula shown as formula (3). By continuously feeding the mixed solution of reaction materials into the reactor to carry out enamination reaction, enamination reaction is continuously performed; continuous production of aromatic acetaldehyde compounds is achieved, reaction time is shortened, and reaction efficiency is improved.
Enamine compound synthesis method and aromatic aldehydes synthetic method of the compound (by machine translation)
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Paragraph 0064; 0065; 0066; 0067; 0068, (2017/12/09)
The invention provides a method for synthesis of a enamine compound and aromatic aldehydes synthetic method of the compound. Enamine compound of synthetic method comprises the starting raw materials with A N, N - dimethyl formamide dimethyl acetal to form a mixed solution; and the mixed solution is continuously fed into the continuous reactor in the alkene amination reaction to obtain the enamine compound B, and alkene amination reaction in continuous enamine compound discharged from the continuous reactor in B; A starting material of formula (1) shown in the structural formula of, enamine compound B formula (2) shown in the structural formula. The reaction of the raw material of the mixed solution and continuously fed into the reactor by way of the alkene amination reaction alkene amination reaction of continuous, then also the continuous production of aromatic aldehyde compound, shortens the reaction time, the reaction efficiency is improved. The continuous reaction method can be stopped at any time according to the actual conditions the reaction or the termination of the reaction, after-treatment can also be based on the need to batch processing or merging processing, is convenient and simple. (by machine translation)
Green catalytic synthesis method nitrobenzaldehyde (by machine translation)
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Paragraph 0022-0024, (2017/02/28)
The invention discloses a method for green-catalytically synthesizing nitrobenzaldehyde. With nitrotoluene as a raw material, the nitrotoluene is firstly reacted with DMF and DMFA to generate N,N-dimethylnitrostyrylamine, and then the N,N-dimethylnitrostyrylamine is oxidized to generate the nitrobenzaldehyde with hydrogen peroxide as a green oxidizing agent and a metal Schiff base as a catalyst. The method is green, environmental-protective, low in cost, mild in reaction conditions and increased in yield when being compared with a method in the prior art.
Facile, environmentally friendly synthesis of benzaldehyde and phenylacetaldehyde analogs from readily available toluene derivatives
Dai, Liyan,Yu, Jie,Chen, Yingqi,Yu, Shichao
scheme or table, p. 3078 - 3084 (2011/09/14)
A facile environmentally friendly synthesis of bezaldehyde and phenylacetaldehyde analogs from readily available toluene derivatives is described. Oxidation of the styrylamines by H2O2 H2O2 affords benzaldehydes in moderate yields, while the hydrolysis of styrylamines afforded phenylacetaldehyde analogs in good yields. Copyright
(1,2,3-Triazol-4-yl)benzenamines: Synthesis and activity against VEGF receptors 1 and 2
Kiselyov, Alexander S.,Semenova, Marina,Semenov, Victor V.
scheme or table, p. 1344 - 1348 (2009/11/30)
Derivatives of (1,2,3-triazol-4-yl)benzenamines are described as potent and ATP-competitive inhibitors of vascular endothelial growth factor receptors I and II (VEGFR-1/2). A number of compounds exhibited VEGFR-2 and VEGFR-1 inhibitory activity comparable
Nitropyrazoles: XII. Transformations of the 4-methyl group in 1,4-dimethyl-3,5-dinitropyrazole and cyclization of the transformation products
Zaitsev,Dalinger,Starosotnikov,Kachala,Strelenko,Shkineva,Shevelev
, p. 1507 - 1515 (2007/10/03)
A preparative procedure for the synthesis of 1,4-dimethyl-3,5- dinitropyrazole by nitration of 1,4-dimethylpyrazole was developed. The reaction of 1,4-dimethyl-3,5-dinitropyrazole with dimethoxymethyl-(dimethyl)amine (N,N-dimethylformamide dimethyl acetal) gave (E)-N,N-dimethyl-2-(1-methyl-3,5- dinitropyrazol-4-yl)ethenylamine. Acid hydrolysis of the latter afforded (1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde, and the reaction with sodium nitrite in hydrochloric acid led to formation of 2-hydroxymino-2-(1-methyl-3,5- dinitropyrazol-4-yl)acetaldehyde. The corresponding O-methyloxime and phenylhydrazone reacted with K2CO3 to give 6-methyl-4-nitropyrazolo[4,3-d]isoxazole-3-carbaldehyde O-methyloxime and 1-methyl-3-nitro-4-(2-phenyl-2H-1,2,3-triazol-4-yl)pyrazol-5-ol, respectively. Treatment of (1-methyl-3,5-dinitropyrazol-4-yl)-acetaldehyde with benzenediazonium chloride gave (1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde phenylhydrazone which underwent intramolecular cyclization with replacement of the 5-nitro group by the action of K2CO3 in acetonitrile; in the reaction with K2CO3 in ethanol, the 5-nitro group was replaced by ethoxy.
Synthesis of deuterium labelled desulfoglucosinolates as internal standards for LC-MS analysis
Robertson, Avril A. B.,Botting, Nigel P.
, p. 13269 - 13284 (2007/10/03)
The syntheses of three deuterium labelled desulfoglucosinolates are described. These are the phenethyl, 1- methoxyindolyl and 4-methoxyindolyl derivatives. The compounds were prepared as internal standards for use in the quantitative LC-MS analysis of glu
