614-75-5Relevant academic research and scientific papers
Preparation method of benzofuranone (by machine translation)
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Paragraph 0008; 0010; 0012; 0014; 0016; 0018, (2020/05/05)
To the preparation method . o-hydroxyacetophenone as a starting material, firstly undergoes Willgerodt - Kindler reaction to obtain phenylacetic acid, and then undergoes intramolecular esterification to obtain the final product benzofuranone, the reaction yield is higher, more efficiently . and compared with the traditional synthesis method, the reaction yield is higher, operation is easy. (by machine translation)
Synthetic method of benzofuranone
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Paragraph 0057; 0059; 0063-0064, (2020/06/16)
The invention provides a synthetic method of benzofuranone. According to the method, o-cresol which is relatively easy to obtain is used as an initial raw material, and the target product benzofuranone is prepared through four-step reaction; and the whole preparation process is mild in condition, high in yield, easy to operate, small in environmental pollution and suitable for large-scale industrial production.
Method for synthesizing benzofuranone by taking O-chlorotoluene as raw material
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, (2020/06/16)
The invention provides a method for synthesizing benzofuranone by taking o-chlorotoluene as a raw material. According to the method, the target product benzofuranone is prepared by taking the easily-available o-chlorotoluene as the initial raw material, and the whole preparation process is mild in condition, high in yield and suitable for large-scale industrial production.
Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents
Hu, Yuheng,Wang, Bing,Yang, Jie,Liu, Teng,Sun, Jie,Wang, Xiaojing
, p. 15 - 30 (2018/10/31)
A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs) formation inhibitory. Most compounds exhibited significant antioxidant and AGEs formation inhibitory activities. Anti-diabetic activity studies showed that compounds 11 and 17 were equipotent to the standard drug glibenclamide in vivo. According to the experimental results, the target compound 35 can be used as a lead compound for the development of new anti-diabetic drugs. The whole experiment showed that anti-diabetic activity is prevalent in 3-arylcoumarins, which added a new natural skeleton to the development of anti-diabetic active drugs.
Benzofuran -2 - (3 H) - ketone
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Paragraph 0030; 0041; 0036; 0037; 0042; 0043; 0048; 0049, (2019/07/04)
The invention discloses a benzofuran - 2 - (3 H) - one of the preparation method, is divided into two steps: (1) preparation of O-hydroxy acetic acid: in acidic conditions or under alkaline conditions, the cyclohexyl - 2 - enone, glyoxalic acid, solvent in the reactor reaction, after the completion of the reaction, the solvent is recovered, by the re-crystallization O-hydroxy acetic acid pure product; (2) benzofuran - 2 - (3 H) - ketone preparation: the belt water trap is added into the reactor in step (1) preparation of ortho-hydroxy acetic acid, then adding solid catalyst and solvent, heating reflux reaction, to no longer have a water drop, cooling to room temperature, filter, to filter the solid catalyst, pressure reducing and recovering the solvent, by recrystallization to obtain benzofuran - 2 - (3 H) - one. In the invention of the cheap raw material, the main material cyclohex - 2 - enone by cyclohexanone in the non-water system and be prepared by chlorine chloride 2 - [...], again obtained by eliminating the; a commercialization of the glyoxylic acid 50% aqueous solution, synthetic route of this invention short and simple operation, high yield, low cost, three waste is greatly reduced.
Design and synthesis of novel senkyunolide analogues as neuroprotective agents
Fang, Yuanying,Wang, Rikang,Wang, Qi,Sun, Yongbing,Xie, Saisai,Yang, Zunhua,Li, Min,Jin, Yi,Yang, Shilin
, p. 668 - 672 (2018/01/27)
A class of senkyunolide analogues bearing benzofuranone fragment were designed, synthesized and evaluated for their neuroprotective effect in models of oxygen glucose deprivation (OGD) and oxidative stress. All tested compounds showed neuroprotection profile based on the cell viability assay. In particular, derivatives 1f–1i possessing furoxan-based nitric oxide releasing functionality exhibited significant biological activities in OGD models. More importantly, compound 1g containing short linker with furoxan displayed the most potent neuroprotection at the concentration of 100 μM (cell survival up to 145.2%). Besides, 1g also showed the middle level neuroprotective effect in model of oxidative stress.
Directed ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalation
Miah, M. A. Jalil,Sibi, Mukund P.,Chattopadhyay,Familoni, Oluwole B.,Snieckus, Victor
, p. 440 - 446 (2017/12/15)
The directed ortho-lithiation reactions of O-aryl N,N-dialkylcarbamates as well as O-1-naphthyl and O-2-naphthyl N,N-dialkylcarbamates with sec-butyllithium/tetramethylethylenediamine (sBuLi/TMEDA) followed by quenching with various electrophiles afford a range of polysubstituted aromatic compounds. If the solutions of the ortho-lithiated carbamates are warmed to room temperature without the addition of external electrophiles, salicylamide and 1- and 2-hydroxynaphthamide derivatives are formed through anionic ortho-Fries rearrangements. The relative stabilities and reactivities of different O-aryl N,N-dialkylcarbamates were investigated. The lateral metalation of 2-tolyl carbamates with lithium diisopropylamide (LDA) provides a route to benzo[b]furan-2(3H)-ones. Previously reported results are used in a comparison of seven O-based directed metalation groups in reactions with several electrophiles. The described methodology is useful for the preparation of 1,2,3-substituted aromatic compounds.
Synthetic method of benzofuran-2(3H)-one
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Paragraph 0020, (2017/05/25)
The invention discloses a synthetic method of benzofuran-2(3H)-one. The method comprises the following steps: hydrolyzing o-clorophenylacetic acid by using a sodium hydroxide solution under the catalysis of a catalyst to generate sodium 2-hydroxyphenylacetate, adding hydrochloric acid to acidify the above obtained reaction solution, cooling for crystallizing the above obtained acidification product, filtering obtained crystals to obtain sodium chloride-containing 2-hydroxyphenylacetic acid, and carrying out a lactonization reaction in a water carrying agent under the catalysis of iron sulfate to generate benzofuran-2(3H)-one. The method has the advantages of simplicity, easiness in implementation, good economic property, high yield, realization of operation simplification, 2-hydroxyphenylacetic acid loss avoiding and yield increase due to omission of the 2-hydroxyphenylacetic acid purifying process by carrying out the lactonization reaction on sodium chloride-containing crude 2-hydroxyphenylacetic acid directly used as a raw material, and realization of small corrosion to a reaction device, difficult in product carbonization, small catalysis use amount, no complex post-treatment, production cost saving and reduction of generation of three wastes due to iron sulfate being a neutral substance.
NEW INSIGTHS on the KINETICS and MECHANISM of the ELECTROCHEMICAL OXIDATION of DICLOFENAC in NEUTRAL AQUEOUS MEDIUM
Cid-Cerón,Guzmán-Hernández,Ramírez-Silva,Galano,Romero-Romo,Palomar-Pardavé
, p. 92 - 98 (2016/06/01)
The diclofenac (DCF) electrochemical oxidation mechanism was studied through: linear voltammetry (LV), chronoamperometry (CA) sampled-current voltammetry (SCV), potentiostatic coulometry (PC) cyclic voltammetry (CV) under stagnant conditions and linear voltammetry under forced convection conditions (FCLV) over a carbon paste electrode (CPE) from an aqueous medium containing 0.1 M phosphate buffer at pH 7. It was found that the DCF electrochemical oxidation involves an EC mechanism, where the electrochemical reaction is carried out through a one electron-exchange while the chemical reaction involves breaking up the DCF through the nitrogen atom, thereby generating the fragments 2,6 dichloroaniline and 2-(2hydroxyprop-2-enyl)phenol. Reverting the potential scan in the cathodic direction at different scan rates and regardless of its rate, after the oxidation peak, it was found that it was possible to reduce only 38% of the DCF oxidized. The spectrophotometric study carried out during different macro-electrolysis periods allowed observing that the current decrease of the oxidation peak coupled to the DCF absorption (at 270 nm), together with the development of a new spectrophotometric absorption maximum (450 nm), all confirm the EC mechanism proposed. With the use of several experimental techniques (CA, LV and FCLV) and theoretical ones using the Stokes-Einstein approach, the DCF diffusion coefficient was determined, this being in average 8.1 × 10-6 cm2 s-1.
Photogenerated α,n-didehydrotoluenes from chlorophenylacetic acids at physiological pH
Ravelli, Davide,Protti, Stefano,Fagnoni, Maurizio
supporting information, p. 852 - 858 (2015/03/05)
Aromatic diradicals are recognized as promising intermediates for DNA cleavage, but their formation has thus far been limited to the Bergman and Myers-Saito cycloaromatizations. We report here the phototriggered generation of all isomers of the potential DNA-cleaving α,n-didehydrotoluene diradicals at physiological pH, accomplished by the irradiation of chlorophenylacetic acids under mild conditions. The desired diradicals were formed upon photolysis of the chosen aromatic in aqueous phosphate buffer solution (pH = 7.3), with the consecutive elimination of biologically compatible chloride ion and carbon dioxide. Theoretical simulations reveal that the efficient decarboxylation of the primarily generated phenyl cations involves a previously not known diradical structure.
