4265-27-4Relevant academic research and scientific papers
Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate
Liu, Juyan,Tian, Miaomiao,Li, Ankun,Ji, Liangshuo,Qiu, Di,Zhao, Xia
supporting information, (2021/02/01)
A Br?nsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF3-substituted benzofuran derivatives were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation procedure of 1-methoxy-2-(arylethynyl)benzenes were also realized by engaging FeCl3 as the catalyst.
Palladium complexes with an annellated mesoionic carbene (MIC) ligand: Catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives
Bera, Jitendra K.,Daw, Prosenjit,Reshi, Noor U Din,Tyagi, Akshi
supporting information, p. 15238 - 15248 (2020/11/18)
Two Pd(ii) complexes (1 and 2) featuring a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand have been synthesized and structurally characterized. Both complexes effectively catalyze the one-pot synthesis of benzofuran starting from phenylacetylene and 2-iodophenol under mild conditions. Complex 1 is found to be an excellent catalyst for the straightforward access to a library of benzofuran, indole, isocoumarin and isoquinolone derivatives by the reaction of terminal alkynes with 2-iodo derivates of phenol, N-methyl aniline, benzoic acid and N-methyl benzamide, respectively. The general utility of the catalytic method is demonstrated using a variety of diversely substituted terminal alkynes and the corresponding desired products are obtained in good to excellent yields. On the basis of control experiments, a two-cycle mechanism is proposed which involves the Sonogashira coupling of 2-iodo derivatives with alkynes and the subsequent cyclization of the corresponding 2-alkynyl compounds.
PALLADIUM ACYCLIC DIAMINOCARBENE COMPLEXES AS PRECATALYSTS FOR HIYAMA COUPLING AND THE TANDEM ONE-POT FLUORIDE FREE HIYAMA COUPLING/CYCLIZATION FOR THE SYNTHESIS OF BIOLOGICALLY RELEVANT
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Paragraph 0108; 0109; 0114-0115, (2020/05/06)
The present invention provides Acyclic diaminocarbene complex of formula (I): Wherein, M is palladium; X is monoanionic ligand selected from Cl, Br or I; Where R1 is different from R2; R1 is selected from the group consisting of alkyl or aryl, each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms; R2 is selected from the group consisting of alkyl, or aryl each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms. The said palladium diamino carbine complex of the present invention are particularly useful as catalyst from Hiyama cross-coupling reaction.
A 2 - substituted benzofuran compound of the catalytic synthesis method
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Paragraph 0016; 0017; 0018, (2019/05/22)
The invention discloses a 2 - substituted benzofuran compound of the catalytic synthesis method, comprises the following steps: normal temperature and pressure, the 2 - alkynyl substituted phenol dissolved in acetonitrile, wherein the 2 - alkynyl substituted phenol with acetonitrile molar volume ratio of 1: 1mmol/mL, to obtain 2 - alkynyl substituted phenol acetonitrile solution; and then to the acetonitrile solution in adding cuprous chloride and cesium carbonate, wherein the cuprous chloride and cesium carbonate of respectively the molar consumption of 2 - alkynyl-substituted phenol mole amount of 5%; after, room temperature stirring 6 hours, produced by the reaction of 2 - substituted benzofuran compound. The invention 2 - substituted benzofuran compound of the catalytic method for synthesis of low cost, high yield, its preparation 1 g of 2 - substituted benzofuran compounds required the cost of the catalyst the prior by iridium catalyst is a catalyst of the synthetic method has lowered 2 orders of magnitude, to improve the yield of the 88.5 - 95.8%.
Preparation method of amiodarone hydrochloride
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Paragraph 0013; 0019-0026, (2019/08/12)
The invention relates to a preparation method of amiodarone hydrochloride. According to the preparation method, synthesis of intermediate 2-butylbenzofuran is realized under effect of a catalyst, a cocatalyst, and an acid binding agent, through Sonogashira coupling cyclization reaction of 2-iodo phenol and 1-acetylene in an organic solvent at a 2-iodo phenol to 1-acetylene molar ratio of 1:09-1.3,wherein reaction temperature ranges from 30 to 60 DEG C, and reaction time ranges from 12 to 38h. Compared with the prior art, the advantages are that: operation is simplified; operation convenienceand product stability are improved; controlling of the ratio of the catalyst to the materials is capable of increasing the purities and yields of intermediates; no column chromatography purifying is needed; cost is reduced; production efficiency is increased at the same time; and convenience is provided for industrial large scale production.
CuI catalyzed domino coupling–cyclization of 2-iodo-phenols and 1-alkynes to the synthesis of 2-substituted benzo[b]furans/furo-pyridines
Chen, Ze-Pin,Zhou, Yi,Shui, Meng-Zhu,Liu, Feng
supporting information, p. 133 - 136 (2018/12/11)
CuI/proline-catalyzed coupling reaction of 2-iodo-phenols with terminal alkynes and the following cyclization process is carried out successively in DMSO at 80 °C. Under this tandem process, 2-substituted benzo[b]furans/furo-pyridines were synthesized in good to excellent yields with a great diversity.
Heterogeneous Nickel-Catalyzed Cross-Coupling between Aryl Chlorides and Alkyllithiums Using a Polystyrene-Cross-Linking Bisphosphine Ligand
Yamazaki, Yuki,Arima, Nozomi,Iwai, Tomohiro,Sawamura, Masaya
supporting information, p. 2250 - 2254 (2019/03/21)
A polystyrene-cross-linking bisphosphine ligand PS-DPPBz was used for Ni-catalyzed cross-coupling with organolithiums. A bench-stable precatalyst [NiCl2(PS-DPPBz)] enabled efficient coupling reactions between aryl chlorides and alkyllithiums. The heterogeneous Ni system showed good reusability. (Figure presented.).
Indium(III)-Catalyzed Synthesis of Benzo[ b]furans by Intramolecular Hydroalkoxylation of ortho-Alkynylphenols: Scope and Mechanistic Insights
Alonso-Mara?ón, Lorena,Martínez, M. Montserrat,Sarandeses, Luis A.,Gómez-Bengoa, Enrique,Pérez Sestelo, José
, p. 7970 - 7980 (2018/06/22)
Indium(III) halides catalyze the hydroalkoxylation reaction of ortho-alkynylphenols to afford benzo[b]furans in good yields. The reaction proceeds with 5-endo-dig regioselectivity with a variety of phenols functionalized at the arene and alkyne moieties in high yields using InI3 (5 mol %) in DCE. Experimental and computational studies support a mechanism based on the indium(III) π-Lewis acid activation of the alkyne followed by nucleophilic addition of the phenol and final protodemetalation to afford the corresponding benzo[b]furan. DFT calculations suggest that dimer In2I6 is the catalytic species through a novel double coordination with the alkyne and the hydroxyl group.
Preparation method of amiodarone hydrochloride intermittent
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Paragraph 0019; 0055; 0058; 0064; 0067; 0072; 0075, (2019/01/13)
The invention belongs to the field of medicine synthesis, and relates to a preparation method of an amiodarone hydrochloride intermittent. The method is characterized by including the following stepsthat 1, under an alkaline condition, in the presence of a phase transfer catalyst, a compound 1 and a compound 2 are subjected to nucleophilic substitution reaction to obtain a compound 3; 2, under analkaline condition, the compound 3 is hydrolyzed to generate a compound 4; 3, the compound 4 is subjected to intramolecular aldol condensation, decarboxylation and dehydration to obtain a compound 5;4, a compound 6 and thionyl chloride are subjected to heating reaction to obtain a compound 7; 5, under the presence of lewis acid, the compound 5 and the compound 7 are subjected to friede-crafts acylation reaction to obtain a compound 8; 6, under the presence of lewis acid, the compound 8 is subjected to demethylation to generate a compound 9, namely the amiodarone hydrochloride intermittent 2-butyl-3-(4-hydroxybenzoyl)benzofuran. The preparation method of the amiodarone hydrochloride intermittent has the advantages of being short in reaction time, high in product purity and high in yield,and the amiodarone hydrochloride intermittent is suitable for large-scale industrial production.
Preparation method of amiodarone hydrochloride intermediate 2-butylbenzofuran
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Paragraph 0050; 0051; 0057, (2018/11/03)
The invention relates to a preparation method of an amiodarone hydrochloride intermediate 2-butylbenzofuran. The preparation method comprises the following steps: A, with methyl 2-(2-aldehydephenoxy)hexanoate as a reaction substrate, under the action of potassium carbonate and potassium iodide, reacting in an organic solvent until a raw material disappears; B, adding water and an organic solvent into a reaction solution obtained in the step A, thoroughly stirring for extracting, separating out an organic phase, drying and then concentrating under reduced pressure to obtain yellow transparent liquid 2-butylbenzofuran. The 2-butylbenzofuran prepared by the preparation method is high in purity; the operation is simple; use of cumbersome column chromatography is avoided; the preparation methodis suitable for large-scale industrial production.
