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135-77-3Relevant articles and documents
Development of a catalytic aromatic decarboxylation reaction
Dickstein, Joshua S.,Mulrooney, Carol A.,O'Brien, Erin M.,Morgan, Barbara J.,Kozlowski, Marisa C.
, p. 2441 - 2444 (2007)
A palladium-catalyzed aromatic decarboxylation reaction has been developed. With electron-rich aromatic adds, the reaction proceeds efficiently under fairly mild conditions in good yields. The method was useful with complex functionalized substrates containing hindered carboxylic adds.
Syntheses of benzophenone-xanthone hybrid polyketides and their antibacterial activities
Kodama, Takeshi,Ito, Takuya,Dibwe, Dya Fita,Woo, So-Yeun,Morita, Hiroyuki
, p. 2397 - 2400 (2017)
Muchimangins are benzophenone-xanthone hybrid polyketides produced by Securidaca longepedunculata. However, their biological activities have not been fully investigated, since they are minor constituents in this plant. To evaluate the possibility of muchimangins as antibacterial agent candidates, five muchimangin analogs were synthesized from 2,4,5-trimethoxydiphenyl methanol and the corresponding xanthones, by utilizing p-toluenesulfonic acid monohydrate for the Br?nsted acid-catalysis. The antibacterial assays against Gram-positive bacteria, Staphylococcus aureus and Bacillus subtilis, and Gram-negative bacteria, Klebsiella pneumoniae and Escherichia coli, revealed that the muchimangin analogs (±)-1,3,6,8-tetrahydroxy-4-(phenyl-(2′,4′,5′-trimethoxyphenyl)methyl)-xanthone (1), (±)-1,3,6-trihydroxy-4-(phenyl-(2′,4′,5′-trimethoxyphenyl)methyl)-xanthone (2), and (±)-1,3-dihydroxy-4-(phenyl-(2′,4′,5′-trimethoxyphenyl)methyl)-xanthone (3) showed significant activities against S. aureus, with MIC values of 10.0, 10.0, and 25.0?μM, respectively. Analogs (±)-1 and (±)-2 also exhibited antibacterial activities against B. subtilis, with MIC values of 50.0 and 12.5?μM, respectively. Furthermore, (+)-3 enhanced the antibacterial activity against S. aureus, with a MIC value of 10?μM.
Synthetic method of medical intermediate 1,2,4-trimethoxybenzene
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Paragraph 0008-0029, (2018/07/30)
The invention discloses a synthetic method of medical intermediate 1,2,4-trimethoxybenzene. According to the synthetic method of medical intermediate 1,2,4-trimethoxybenzene, 1,2,4-triacetoxybenzene,methanol, potassium hydroxide, dimethyl sulphate, potassium carbonate, 2-aminoterephthalic acid, zirconium tetrachloride, and terephthalaldehyde are taken as main raw materials; 2-aminoterephthalic acid and zirconium tetrachloride ultrasound-assisted synthesis of a nanometer catalyst is adopted so as to realize free adsorption and desorption of reactant molecules and product molecules, realize diffusion, and at the same time achieve relatively high selectivity on products; Schiff base modification reaction with terephthalaldehyde is adopted to increase the catalytic activity of the catalyst onorganic molecule 1,2,4-trimethoxybenzene, reduce the energy barrier of the intermediate synthesis reaction system, and accelerate reaction speed. In intermediate synthesis process, the pH value of anobtained mixed solution and the dropwise adding speed of dimethyl sulphate are controlled strictly, dichloromethane is adopted for a plurality of extraction purification, so that product yield is increased greatly, production cost is reduced, production time is shortened, and excellent catalytic effect on synthesis reaction of 1,2,4-trimethoxybenzene is achieved.
A ligand-free, powerful, and practical method for methoxylation of unactivated aryl bromides by use of the CuCl/HCOOMe/MeONa/MeOH system
Guo, Ying,Ji, Si-Zhe,Chen, Cheng,Liu, Hong-Wei,Zhao, Jian-Hong,Zheng, Yu-Lin,Ji, Ya-Fei
, p. 8651 - 8664 (2015/03/05)
A ligand-free, powerful, and practical method for mono and polymethoxylation of unactivated aryl bromides has been developed; CuCl was used as catalyst, HCOOMe as cocatalyst, and methanolic MeONa as both nucleophile and solvent. This eco-friendly procedure is characterized by operational simplicity, inexpensive substrates (unactivated mono to polybromoarenes), full conversion, and direct recovery of pure MeOH.
Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes
Mudududdla, Ramesh,Sharma, Rohit,Abbat, Sheenu,Bharatam, Prasad V.,Vishwakarma, Ram A.,Bharate, Sandip B.
supporting information, p. 12076 - 12079 (2015/02/19)
A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C-C bond cleavage followed by intermolecular [4+2]-Diels-Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist. This journal is
Magnesium oxide as a heterogeneous and recyclable base for the N-methylation of indole and O-methylation of phenol using dimethyl carbonate as a green methylating agent
Gadge, Sandip T.,Mishra, Ashish,Gajengi, Aravind L.,Shahi, Nileshkumar V.,Bhanage, Bhalchandra M.
, p. 50271 - 50276 (2014/12/10)
This work reports a mild efficient and sustainable protocol for N-methylation of indole and O-methylation of phenol using dimethylcarbonate as an environmentally safe, non-toxic, biodegradable and green methylating agent under microwave conditions. Magnesium oxide (MgO) has been employed as a heterogeneous and recyclable base for clean N-methylation of indole and O-methylation of phenol with dimethylcarbonate. Basic properties of the fresh and recycled MgO were measured by temperature programmed desorption (CO2-TPD) analysis. The CO2-TPD runs suggested that both strong and moderately basic sites are present on the oxide, while only the moderately basic sites are responsible for the N-and O-methylation of indole and phenol, respectively, using DMC as a methylating agent. The CO2-TPD analysis showed that the basic sites on fresh and recycled MgO were comparable. The MgO was isolated by simple filtration and recycled efficiently without loss in activity and selectivity.
Mild aromatic palladium-catalyzed protodecarboxylation: Kinetic assessment of the decarboxylative palladation and the protodepalladation steps
Dickstein, Joshua S.,Curto, John M.,Gutierrez, Osvaldo,Mulrooney, Carol A.,Kozlowski, Marisa C.
, p. 4744 - 4761 (2013/07/11)
Mechanism studies of a mild palladium-catalyzed decarboxylation of aromatic carboxylic acids are described. In particular, reaction orders and activation parameters for the two stages of the transformation were determined. These studies guided development of a catalytic system capable of turnover. Further evidence reinforces that the second stage, protonation of the arylpalladium intermediate, is the rate-determining step of the reaction. The first step, decarboxylative palladation, is proposed to occur through an intramolecular electrophilic palladation pathway, which is supported by computational and mechanism studies. In contrast to the reverse reaction (C-H insertion), the data support an electrophilic aromatic substitution mechanism involving a stepwise intramolecular protonation sequence for the protodepalladation portion of the reaction.
Pd-catalyzed cross-coupling of aryl carboxylic acids with propiophenones through a combination of decarboxylation and dehydrogenation
Zhou, Jun,Wu, Ge,Zhang, Min,Jie, Xiaoming,Su, Weiping
supporting information; experimental part, p. 8032 - 8036 (2012/08/13)
A palladium-catalyzed cross-coupling reaction of aryl carboxylic acids with saturated propiophenones through a combination of decarboxylation and dehydrogenation to form Heck-type products was reported. In a glove box, a 25 mL tube equipped with a stir bar was charged with Pd(OAc)2, PCy3, propiophenone, 2-nitrobenzoic acid, Ag2CO3 and nBu4NOAc HOAc. Then, the mixture was heated under nitrogen at 90°C in DMF for 24 h. After cooling down, the crude reaction mixture was analyzed by GC with n-dodecane as an internal standard to obtain 3a in 75% GC yield. Relatively weak bases, such as carboxylate salts, facilitated this reaction and the effect of the bases was a function of their solubility, while strong bases, such as K3PO4 and K2CO3 shut down the reaction completely. The simultaneous use of carboxylate salts and equimolar carboxylic acids significantly improved the yield of 3a, although the use of acetic acid alone was ineffective for the reaction.
Biaryl crosslinkers. I. Crosslinking of a bisazidobiaryl with poly(3-hexylthiophene)
Lohani, Jaya,Balakrishnan,Gaur, Manoj,Raghunathan,Eswaran
, p. 549 - 554 (2011/10/03)
A new biaryl-based bisazide has been used to crosslink poly(3- hexylthiophene), a conducting polymer useful for organic electronics. Crosslinking was monitored using infrared spectroscopy and film morphology was studied using scanning electron microscopy. Hole mobility studies of the devices prepared from pristine and crosslinked polymer show an increase in hole mobility of one order of magnitude for the latter devices.
Chemistry of renieramycins. Part 9: Stereocontrolled total synthesis of (±)-renieramycin G
Yokoya, Masashi,Shinada-Fujino, Kimiko,Saito, Naoki
body text, p. 2446 - 2449 (2011/05/16)
A 25-step stereocontrolled total synthesis of (±)-renieramycin G (1g) from readily available 2-hydroxy-3-methyl-4,5-dimethoxybenzaldehyde (3) is described. This synthesis features the concise construction of the pentacyclic framework using the stereoselective Pictet-Spengler type cyclization reaction of lactam (14) with ethyl diethoxyacetate, followed by the base-catalyzed isomerization of the C-1 stereo center.
