- Preparation method and application of propyne aryl ether compound
-
The invention particularly relates to a method for preparing propyne aryl ether compounds from aryl phenol, halogenated propyne and derivatives of the halogenated propyne, and belongs to the technical field of preparation of the propyne aryl ether compoun
- -
-
Paragraph 0065-0066
(2021/08/28)
-
- Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes
-
Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.
- Lasányi, Dániel,Tolnai, Gergely L.
-
supporting information
p. 10057 - 10062
(2019/12/24)
-
- Waste-minimised copper-catalysed azide-alkyne cycloaddition in Polarclean as a reusable and safe reaction medium
-
Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide-alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium. The process is very efficient, affording in 24 out of the 26 tested cases the desired triazole in quantitative yields. Product isolation is also very convenient, since the triazoles either precipitate or form a separate liquid phase, without the need to perform chromatographic separations. Moreover, since the metal catalyst is retained in the Polarclean/water phase, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without an apparent loss in efficiency. This methodology is associated with very limited waste production, as evidenced by calculated E-factors in the range 2.6-3.7.
- Luciani, Lorenzo,Goff, Emily,Lanari, Daniela,Santoro, Stefano,Vaccaro, Luigi
-
supporting information
p. 183 - 187
(2018/01/17)
-
- Synthesis of Tricyclic Isoxazoles via Sequential [3+2] Dipolar Cycloaddition and Palladium-Catalyzed Intramolecular Arylation Reactions
-
An efficient synthetic route to tricyclic isoxazoles via sequential copper-catalyzed 1,3-dipolar cycloaddition and palladium-catalyzed intramolecular arylation of isoxazoles is described. Based on these reactions, a convenient one-pot synthesis of the tri
- Guo, Dong-Cai,Zhang, Chao,Li, Fei,Zhang, Fenghua,Yu, Fang,He, Yu-Peng
-
p. 1356 - 1370
(2017/03/11)
-
- NOVEL PYRDAZINONE HERBICIDES
-
Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides wherein R1, R2, G and W are as defined in the disclosure, and A is
- -
-
Page/Page column 54
(2017/05/17)
-
- Aryl radical cyclization with alkyne followed by tandem carboxylation in methyl 4-tert-butylbenzoate-mediated electrochemical reduction of 2-(2-propynyloxy)bromobenzenes in?the presence of carbon dioxide
-
Constant current electrolysis of 2-(2-propynyloxy)bromobenzenes in DMF using an undivided cell equipped with a Pt cathode and an Mg anode in the presence of carbon dioxide and an electron transfer mediator, methyl 4-tert-butylbenzoate, resulted in aryl ra
- Katayama, Asahi,Senboku, Hisanori,Hara, Shoji
-
p. 4626 - 4636
(2016/07/18)
-
- Synergistic steric effects in the development of a palladium-catalyzed alkyne carbohalogenation: Stereodivergent synthesis of vinyl halides
-
We report our finding that by exploiting the synergistic steric effects between substrate and catalyst, an intramolecular Pd-catalyzed alkyne carbohalogenation can be achieved. This operationally simple method uses the bulky Pd/ Q-Phos combination and all
- Le, Christine M.,Menzies, Perry J. C.,Petrone, David A.,Lautens, Mark
-
supporting information
p. 254 - 257
(2015/02/19)
-
- Synthesis of Potential Bioactive Novel 7-[2-Hydroxy-3-(1,2,3-triazol-1-yl) propyloxy]-3-alkyl-4-methylcoumarins
-
A series of 50 novel 7-[2-hydroxy-3-(1,2,3-triazol-1-yl)propyloxy]-3-alkyl-4-methylcoumarins had been designed and synthesized in good to excellent yields via Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction "click chemistry" of 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarins with variety of acetylene derivatives. In turn, the precursor compound, that is, 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarin, was synthesized by condensation of epichlorohydrin with 7-hydroxy-3-alkyl-4-methylcoumarins followed by opening of the epoxide ring in the resulted 7-epoxymethoxy-3-alkyl-4-methylcoumarins with sodium azide. All the synthesized compounds were unambiguously identified on the basis of their spectral data analyses (IR, 1H-NMR, 13C-NMR spectra, and HRMS).
- Arya, Anu,Kumar, Vinod,Mathur, Divya,Singh, Sukhdev,Brahma, Raju,Singh, Rajpal,Singh, Seema,Sharma,Parmar, Virinder S.,Prasad, Ashok K.
-
-
- Novel One-Pot Synthetic Method for Propargyl Alcohol Derivatives from Allyl Alcohol Derivatives
-
An efficient one-pot procedure for the synthesis of propargyl alcohol derivatives from allyl alcohol derivatives has been developed. The key to this transformation from a C-C double bond to a C-C triple bond is that hydrogen bromide elimination from 1,2-dibromoalkanes that contain a neighboring oxygen functional group is promoted by the inductive electron-withdrawing effect of the oxygen functional group. In the one-pot reaction, tetrabutylammonium hydroxide was the best base, and the addition of molecular sieves 13X also promoted the reaction.
- Kutsumura, Noriki,Inagaki, Mai,Kiriseko, Akito,Saito, Takao
-
p. 1844 - 1850
(2015/06/30)
-
- Synthesis and biological evaluation of 4-(1,2,3-triazol-1-yl)coumarin derivatives as potential antitumor agents
-
In this research, a series of 4-(1,2,3-triazol-1-yl)coumarin conjugates were synthesized and their anticancer activities were evaluated in vitro against three human cancer cell lines, including human breast carcinoma MCF-7 cell, colon carcinoma SW480 cell and lung carcinoma A549 cell. To increase the biological potency, structural optimization campaign was conducted focusing on the C-4 position of 1,2,3-triazole and the C-6, C-7 positions of coumarin. In addition, to further evaluate the role of 1,2,3-triazole and coumarin for antiproliferative activity, 9 compounds possessing 4-(piperazin-1-yl)coumarin framework and 3 derivatives baring quinoline core were also synthesized. By MTT assay in vitro, most of the compounds display attractive antitumor activities, especially 23. Further flow cytometry assays demonstrate that compound 23 exerts the antiproliferative role through arresting G2/M cell-cycle and inducing apoptosis.
- Zhang, Wenjuan,Li, Zhi,Zhou, Meng,Wu, Feng,Hou, Xueyan,Luo, Hao,Liu, Hao,Han, Xuan,Yan, Guoyi,Ding, Zhenyu,Li, Rui
-
supporting information
p. 799 - 807
(2014/02/14)
-
- Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: Divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles
-
The controllable synthesis of 3-methylene-2,3-dihydrobenzofurans 2 and 3-methylene-2,3-dihydroindoles 5 has been developed through Rh-catalyzed intramolecular annulation of aromatic rings with azavinyl carbenes. This journal is
- Tang, Xiang-Ying,Zhang, Yong-Sheng,He, Lv,Wei, Yin,Shi, Min
-
supporting information
p. 133 - 136
(2015/01/09)
-
- A facile synthesis of 3-substituted benzofurans and indoles through a palladium-catalyzed domino carbopalladation/CH-activation/isomerization process
-
Novel benzofurans 7 and indoles 8 have been prepared from 3 and 4 by a Pd-catalyzed mono-component three-fold domino carbopalladation/CH-activation/ isomerization process and from 12 and 5 to give 8 by a two-component fourfold domino Sonogashira/carbopall
- Tietze, Lutz F.,Hungerland, Tim,Ammermann, Jonas,Eichhorst, Christoph,Reichmann, Sven O.,Stalke, Dietmar
-
p. 1537 - 1555
(2014/01/17)
-
- ICl-mediated intramolecular twofold iodoarylation of diynes and diynyl diethers and amines: Synthesis of bis(2 H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety
-
Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an al
- Mo, Juntae,Choi, Wonseok,Min, Jiae,Kim, Cheol-Eui,Eom, Dahan,Kim, Sung Hong,Lee, Phil Ho
-
p. 11382 - 11388
(2013/12/04)
-
- PYRROLO SULFONAMIDE COMPOUNDS FOR MODULATION OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORGAMMA, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASES
-
The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administrating these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides pyrrolo sulfonamide compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof.
- -
-
Page/Page column 60
(2012/11/06)
-
- Hybrid system of metal/Bronsted acid relay catalysis for the intramolecular double hydroarylation and cationic cyclization of diyne diethers and diamines
-
We have developed a hybrid system of metal/Bronsted acid relay catalysis for the intramolecular double hydroarylation and cationic cyclization of diyne diethers and diamines to give 4,4′-bi(2H-chromene), bi(2H-quinoline), and dioxafluoranthenes starting f
- Mo, Juntae,Eom, Dahan,Lee, Euichul,Lee, Phil Ho
-
supporting information; experimental part
p. 3684 - 3687
(2012/08/28)
-
- Influence of the acetylenic substituent on the intramolecular carbolithiation of alkynes
-
The intramolecular carbolithiation of a series of propargylic ethers has been performed to evaluate the influence of the terminal substituent on the efficiency and the stereochemical outcome of the cyclization. Our results show that only 5-exo-dig cyclizations are observed, and dihydrobenzofurans are obtained exclusively. Depending on the nature of the terminal substituent, two cases can be considered. If the terminal substituent carried by the acetylenic carbon atom is itself a carbon atom, the cyclization can occur provided the terminal propargylic position bears a coordinating element and is at least disubstituted. When the cyclization occurs, it follows an anti-carbolithiation pathway and thus leads to the E isomer of the exocyclic double bond. Only in one case (Ph) was a mixture of the E and Z isomers of the resulting olefin recovered. The cyclization can also take place if the alkyne is directly substituted by S or Si, provided the cyclization conditions are tuned. In the case of the trimethylsilyl substituent, a syn-carbolithiation was observed. If the double bond is recovered, in most cases, in the exocyclic position, the products can aromatize directly for SPh-substituted substrate 24. Furthermore, in the two latter cases, when alkylation of the vinyllithium intermediate is performed, isomerization of the double bond seems instantaneous. Copyright
- Girard, Anne-Lise,Lhermet, Rudy,Fressigne, Catherine,Durandetti, Muriel,Maddaluno, Jacques
-
experimental part
p. 2895 - 2905
(2012/06/29)
-
- NOVEL LACTAM COMPOUND
-
The present invention provides a novel lactam compound, a sugar transport enhancement agent containing this compound as an active ingredient, an agent for the prevention and/or treatment of diabetes mellitus, diabetic peripheral neuropathy, diabetic nephr
- -
-
Page/Page column 13-14
(2010/11/29)
-
- Dual inhibitors of adipocyte fatty acid binding protein and keratinocyte fatty acid binding protein
-
Compounds that are dual aP2/k-FABP inhibitors are provided having the formula wherein A, B, X, Y, R1, R2 and R3 are as described herein. A method is also provided for treating diabetes and related diseases, especially Type II diabetes, employing dual aP2/k-FABP inhibitors alone or in combination with at least one other antidiabetic agent such as metformin, glyburide, troglitazone and/or insulin.
- -
-
-
- 2-aminoethyl-benzofuran derivatives, preparation thereof and therapeutical use thereof
-
PCT No. PCT/FR97/00383 Sec. 371 Date Aug. 31, 1998 Sec. 102(e) Date Aug. 31, 1998 PCT Filed Mar. 5, 1997 PCT Pub. No. WO97/32870 PCT Pub. Date Sep. 12, 1997Compounds of formula (I), wherein A is a hydrogen atom or a hydroxyl group; B is a hydrogen atom or
- -
-
-
- A convenient preparation of salicylaldehydes from 2-methylbenzofurans by ozonolysis
-
A convenient and effective transformation of 2-methylbenzofuran (B) to salicylaldehyde (C) was achieved by ozonolysis of B in CH2Cl2 at -78°C followed by alkaline hydrolysis.
- Ishii,Ohia,Nashioka,Hayashida,Harayama
-
p. 1166 - 1168
(2007/10/02)
-
- 16-Substituted polyunsaturated hexadecanoic fatty acids
-
Sixteen carbon atom carboxylic acids having 16-phenoxy or 16-phenylthio substituents, and 0, 1, or 4 triple bonds, methods of preparing them, and pharmaceutical preparations containing them. These compounds are useful as lipoxygenase inhibitors.
- -
-
-