Xi:Irritant;
83-34-1Relevant articles and documents
Vapor phase methylation of indole over nanocrystalline Cd1-xCrxFe2O4 (x = 0, 0.25, 0.5, 0.75 and 1.0) ferrospinels
Kadian,Siwach,Gupta,Duhan
, p. 1474 - 1478 (2016)
Vapor phase methylation of indole has been carried out over nanocrystalline Cd1-xCrxFe2O4 (x = 0, 0.25, 0.5, 0.75 and 1.0) ferrospinels in a fixed bed down-flow reactor. Catalyst characterization was performed by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy with EDX, BET surface area and temperature programmed ammonia-desorption method. Product selectivity is shown to be strongly influenced by acidic properties of the catalyst. A maximum yield of 64.29 % of 3-methyl indole with 91.46 % selectivity at 70.3 % indole conversion was obtained under optimized reaction conditions.
CITORELLAMINE, A NEW BROMOINDOLE DERIVATIVE FROM POLYCITORELLA MARIAE
Roll, Deborah M.,Ireland, Chris M.
, p. 4303 - 4306 (1985)
The structure of citorellamine, isolated from the tunicate Polycitorella mariae, has been deduced from spectroscopic analyses and chemical transformations.
A remarkable mechanistic dichotomy in the acid-catalysed decomposition of the N- And C-adducts of indolide anions with 1,3,5-trinitrobenzene
Sepulcri, Patricia,Goumont, Regis,Terrier, Francois,Buncel, Erwin
, p. 2241 - 2243 (1996)
Decomposition of the N- and C-adducts of indolide anions with 1,3,5-trinitrobenzene is subject to specific acid-catalysis in the former case and general-acid-catalysis in the latter through an SEAr process.
Catalytic signal amplification using a heck reaction. An example in the fluorescence sensing of Cu(II)
Wu, Qiaoyin,Anslyn, Eric V.
, p. 14682 - 14683 (2004)
Catalytic signal enhancement using an organometallic reaction is demonstrated. The reactivity of a Heck cross-coupling reaction that creates a fluorophore is modulated by the addition of a polyazacyclam inhibitor. The inhibitor will complex with Cu(II), which restores the activity of the Pd(II). The addition of Cu(II) therefore leads to the generation of fluorescence, thereby creating a very sensitive assay for Cu(II). The rate of the Heck reaction is followed by monitoring emission as a function of time. The rate is proportional to the Cu(II) concentration and correlates to the affinity of the inhibitor to various metals. This strategy represents a general technique that can be exploited with other catalytic organometallic reactions. Copyright
Synthesis of 3-methylindole from glycerol cyclization with aniline over CuCr/Al2O3 catalysts modified by alkali earth oxides
Chen, Yu,Xu, Chenghua,Liu, Chuanqi,Li, Xue,Liu, Jianying,Cao, Yang,Yang, Jie
, p. 263 - 270 (2013)
In the present work, CuCr catalysts supported on γ-Al 2O3 are prepared and modified with alkali earth elements by impregnation, characterized by N2 adsorption-desorption, XRD, H2-TPR (temperature-programmed reduction by H2), CO 2-TPD and NH3-TPD (temperature-programmed desorption of NH3 or CO2), and applied in the synthesis of 3-methylindole (3-MI) with a N-heterocycle from glycerol and aniline in the fixed-bed reactor. The results show that the introduction of alkali earth elements into the CuCr/Al2O3 catalyst can improve the yield of target 3-MI in the order of Mg 2O3 gives rise to a high 3-MI yield of 39.09% and 65.17% in N2 as a carrier gas and 20%H2-N2 mixture gas, respectively. According to catalysts characterization and catalytic tests, the reaction pathway of glycerol cyclization with aniline is proposed, the formation of 3-MI and 3H-indol-3-yl methanol is hypothesized to be through the aniline cyclization with 2,3-hydroxypropanal from glycerol dehydrogenation over Cu0 centers and basic sites. The acidic sites mainly play a role on activating aniline, which interacts with glycerol to form 3-MI or quinoline through cyclization and dehydration.
Ring-methylation of pyrrole and indole using supercritical methanol
Kishida, Nobuhiro,Kamitanaka, Takashi,Fusayasu, Masafumi,Sunamura, Takashi,Matsuda, Tomoko,Osawa, Tsutomu,Harada, Tadao
, p. 5059 - 5064 (2010)
The ring-methylation of pyrrole or indole using supercritical methanol proceeded at 623 K without the further addition of catalysts. Pyrrole produced a mixture of unreacted pyrrole and mono-, di-, tri-, and tetra-methylpyrroles at the reaction time of 8 h. On the other hand, indole was selectively methylated at the C3 position to afford 3-methylindole in 79% yield at the reaction time of 5 h. The ring-methylation of indole using supercritical methanol was claimed to proceed via (1H-indol-3-yl)methanol. The conversion of indole to (1H-indol-3-yl)methanol would be achieved by the electrophilic aromatic substitution between the indol-1-ide (indole anion) and H2C +-OH. The (1H-indol-3-yl)methanol must be reduced to 3-methylindole in the presence of supercritical methanol.
A new efficient approach to 3-methylindole: Vapor-phase synthesis from aniline and glycerol over Cu-based catalyst
Sun, Wei,Liu, Dong-Yan,Zhu, Hai-Yan,Shi, Lei,Sun, Qi
, p. 147 - 150 (2010)
A novel efficient method for vapor-phase synthesis of 3-methylindole from aniline and glycerol has been developed over Cu-based catalysts. The catalysts were characterized by BET, XRD, H2-TPR and NH3-TPD techniques. The results indicated that Cu/SiO2-Al2O 3 catalyst exhibited high activity. The yield of 3-methylindole could be up to 40% when the Cu loading was 5.41 wt% and the reaction temperature was 240 °C. Moreover, the catalyst could be reused without obvious loss of the yield even after reaction time of 46 h. Copper-based catalyst with good dispersion and large amount of weak acid sites was favorable for producing 3-methylindole. A possible reaction pathway for the catalytic synthesis of 3-methylindole was proposed.
Efficient synthesis of 3-methylindole using biomass-derived glycerol and aniline over ZnO and CeO2 modified Ag/SBA-15 catalysts
Gao, Yining,Lin, Shuyi,Qu, Yi,Shi, Lei
, (2020)
An efficient mesoporous catalyst of Ag/SBA-15 modified with ZnO and CeO2 was successfully constructed with the purpose of efficiently synthesizing 3-methylindole by biomass-derived glycerol and aniline, which up to 62% yield and 75% selectivity for 3-methylindole were achieved when Ag loading was 1.00 mmol/g?1, ZnO or CeO2 content was 1.00 or 0.05 mmol/g?1, respectively. And only 3% yield decreased when the catalyst was circulated five times. The characterizations researches on N2 physical adsorption, Fourier transform infrared (FT-IR), scanning electron microscopy and energy-dispersive X-ray spectroscopy (SEM-EDX), temperature programmed reduction of hydrogen (H2-TPR), X-ray diffraction (XRD), transmission electron microscopy (TEM), temperature programmed desorption (TPD) of NH3 and CO2, thermogravimetric and differential thermal analysis (TG-DTA) indicated that adding the promoter of ZnO to Ag/SBA-15 increased the dispersion of the silver particles significantly and controlled the aggregation of Ag nanoparticles during the reaction remarkably because doping ZnO greatly increased the polarity of the composite carrier SBA–15–ZnO and brought about the interaction between Ag and carrier enhanced. CeO2 could promote the reduction of Ag2O and suppress the formation of carbon deposition effectively. In addition, doping ZnO and CeO2 increased the number of the weak-acid centers of the SBA-15 supported Ag-based catalyst observably, thereby the catalyst of Ag/SBA-15-ZnO-–ZnO–CeO2 acquired a good selectivity. Moreover, the reaction pathway for 3-methylindole synthesis by biomass-derived glycerol and aniline was probed in depth and a reasonable route was proposed.
Highly selective synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K2O
Cui, Yan-Xi,Sun, Li-Dong,Sun, Qi,Shi, Lei
, p. 1127 - 1129 (2013)
The vapor-phase synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K2O was investigated. The catalysts were characterized by X-ray diffraction (XRD) and the temperature-programmed desorption of ammonia (NH3-TPD). The effect of the reaction temperature on the activity and selectivity of Cu/NaY-K2O catalyst was also investigated. The results indicated that the addition of K2O to Cu/NaY increased the selectivity of the catalyst remarkably because the amount of middle-strong acid sites decreased clearly. The decrease of the reaction temperature was beneficial for the increase of 3-methylindole selectivity. Over Cu/NaY-K2O, the selectivity of 3-methylindole reached 75% and the yield of the target product was up to 47% at 220 C. A probable catalytic mechanism for the synthesis of 3-methylindole from glycerol and aniline was proposed.
Biotransformation of Indole to 3-Methylindole by Lysinibacillus xylanilyticus Strain MA
Arora, Pankaj Kumar,Dhar, Kartik,Veloz García, Rafael Alejandro,Sharma, Ashutosh
, (2015)
An indole-biotransforming strain MA was identified as Lysinibacillus xylanilyticus on the basis of the 16S rRNA gene sequencing. It transforms indole completely from the broth culture in the presence of an additional carbon source (i.e., sodium succinate). Gas-chromatography-mass spectrometry identified indole-3-acetamide, indole-3-acetic acid, and 3-methylindole as transformation products. Tryptophan-2-monooxygenase activity was detected in the crude extracts of indole-induced cells of strain MA, which confirms the formation of indole-3-acetamide from tryptophan in the degradation pathway of indole. On the basis of identified metabolites and enzyme assay, we have proposed a new transformation pathway for indole degradation. Indole was first transformed to indole-3-acetamide via tryptophan. Indole-3-acetamide was then transformed to indole-3-acetic acid that was decarboxylated to 3-methylindole. This is the first report of a 3-methylindole synthesis via the degradation pathway of indole.
