- Substitution vs. addition. Regioselective electro-bromination of benzofuran
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Regioselective electro-bromination of benzofuran (2) was achieved successfully by an adequate choice of solvents and bromide salts to afford 5-bromobenzofuran (1), 5,7-dibromobenzofuran (3), and 2,3-dibromo-2,3-dihydrobenzofuran (4), respectively. Upon electrolysis of benzofuran (2) in AcOH/H2O (100/1) containing NH4Br, substitution at the C(5)-position of benzofuran (2) proceeded smoothly to afford 5-bromobenzofuran (1). After passage of totally 4 F/mol of electricity in a similar medium, 5,7-dibromobenzofuran (3) was obtained as a sole product. On the other hand, electrolysis of benzofuran (2) in CH2Cl2/H2O (1/1) and/or AcOH/H2O (10/1) in the presence of either NaBr or NH4Br afforded 2,3-dibromo-2,3-dihydrobenzofuran (4), exclusively.
- Tanaka, Hideo,Kawakami, Yusuke,Kuroboshi, Manabu,Torii, Sigeru
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Read Online
- Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening
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The generation of metal carbenoids via ring opening of cyclopropenes by transition metals offers a simple entry into highly reactive intermediates. Herein, we describe a diastereoselective intermolecular rhodium-catalyzed cyclopropanation of heterocycles and alkenes using cyclopropenes as carbene precursors with a low loading of a commercially available rhodium catalyst. The reported method is scalable and could be performed with catalyst loadings as low as 0.2 mol %, with no impact to the reaction yield or selectivity.
- Jeyaseelan, Rubaishan,Lautens, Mark,Ross, Rachel J.
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supporting information
(2020/06/29)
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- REACTIVE MESOGEN, LIQUID CRYSTAL COMPOSITION AND LIQUID CRYSTAL DISPLAY COMPRISING THE SAME
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The invention relates to a reactive mesogen, a liquid crystal composition and a liquid crystal display comprising the same. The reactive mesogen is represented by a chemical formula 1, wherein, X1 andX2 independently are hydrogen or halogen, Y is -O-, -S-
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Paragraph 0108; 0109; 0114; 0115; 0116
(2019/01/24)
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- Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles
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A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.
- Saxena, Paridhi,Maida, Neha,Kapur, Manmohan
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supporting information
p. 11187 - 11190
(2019/09/30)
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- Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C?H Activation with Silyldimesitylborane
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Direct dimesitylborylation of benzofuran derivatives by a C?H activation catalyzed by an iridium(I)/N-heterocyclic carbene (NHC) complex in the presence of Ph2MeSi-BMes2 afforded the corresponding dimesitylborylation products in good to high yield with excellent regioselectivity. This method provides a straightforward route to donor–(π-spacer)–acceptor systems with intriguing solvatochromic luminescence properties.
- Shishido, Ryosuke,Sasaki, Ikuo,Seki, Tomohiro,Ishiyama, Tatsuo,Ito, Hajime
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supporting information
p. 12924 - 12928
(2019/11/05)
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- Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N′-Acyl Arylhydrazines
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A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N′-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.
- Cao, Jun,Chen, Zi-Li,Li, Shu-Min,Zhu, Gao-Feng,Yang, Yuan-Yong,Wang, Cong,Chen, Wen-Zhang,Wang, Jian-Ta,Zhang, Ji-Quan,Tang, Lei
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supporting information
p. 2774 - 2779
(2018/06/21)
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- PYRAZOLE DERIVATIVES AS MALT1 INHIBITORS
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Disclosed are compounds, compositions and methods for treating of diseases, syndromes, conditions, and disorders that are affected by the modulation of MALT1. Such compounds are represented by Formula (I) as follows: wherein R1, R2, R3, R4, R5, R6, R5, G1, and G2 are defined herein.
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- 5-bromo-benzofuran preparation method
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The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 5-bromobenzofuran. The preparation method of 5-bromobenzofuran comprises the following steps: p-bromophenol and 2-bromoacetaldehyde dimethyl aceta
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Paragraph 0022; 0024
(2017/04/06)
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- Visible light-induced monofluoromethylenation of heteroarenes with ethyl bromofluoroacetate
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Visible light-induced monofluoromethylenation of benzofurans and benzothiophenes with ethyl bromofluoroacetate was developed. This method provided a convenient access to novel α-fluoro-α-heteroarylesters under mild reaction conditions.
- Yu, Wei,Xu, Xiu-Hua,Qing, Feng-Ling
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p. 6564 - 6567
(2016/08/09)
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- Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals
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An efficient and environmentally benign heterogeneous catalytic process for the synthesis of 2,3-unsubstituted benzo[b]furans has been established via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals. By utilizing tin-exchanged H-β zeolite (Sn-β) as catalyst, a wide range of functionalized 2,3-unsubstituted benzo[b]furans could be prepared in good to excellent yields. The Sn-β zeolite catalyst also exhibited excellent shape selectivity on the cyclization of meta-substituted 2-aryloxyacetaldehyde acetals, and 6-substituted isomers were preferably formed up to 97% regio-selectivity. Moreover, Sn-β zeolite could be easily recovered and reused without any noticeable activity loss.
- Sun, Nan,Huang, Peng,Wang, Yifan,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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p. 4835 - 4841
(2015/07/27)
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- HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
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Page/Page column 15-16
(2012/11/08)
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- AZABENZIMIDAZOLES AS FATTY ACID SYNTHASE INHIBITORS
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This invention relates to the use of azabenzimidazole derivatives for the modulation, notably the inhibition of the activity or function of fatty acid synthase (FAS). Suitably, the present invention relates to the use of azabenzimidazoles in the treatment of cancer.
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Page/Page column 52
(2011/06/23)
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- PREPARATION OF BENZOFURANS AND USE THEREOF AS SYNTHETIC INTERMEDIATES
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The present invention provides several synthetic methods for preparing N-(2-butylbenzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide, a compound of formula (3), an intermediate in the preparation of Dronedarone. The present invention further provides a process for preparing Dronedarone, comprising the steps of converting 2-butyl-5-bis(methanesulfon)-amidobenzofuran of formula (3) to Dronedarone, wherein the 2-butyl-5-bis(methanesulfon)-amidobenzofuran of formula (3) is prepared by the processes of the present invention.
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Page/Page column 38
(2011/09/15)
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- CONDENSED HETEROCYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I) wherein R1, A, B, D, E, G, Q, Ar, n, m, and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 98
(2010/04/03)
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- 4'-AMINO CYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): formula (I) wherein Cy is selected from formula (Il) and wherein R1, R2, R3, Q, G, Ar, m, n and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 116
(2010/04/06)
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- Synthesis of piperazino-substituted benzo[b]furans as potential CNS agents
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The synthesis of a series of substituted benzofurans is reported. Selected compounds have been shown to bind strongly and with high selectivity to the serotonin receptor 5-HT2A in the presence of the receptor 5-HT 7 in vitro.
- Klenc, Jeff,Strekowski, Lucjan
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experimental part
p. 249 - 252
(2011/06/10)
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- 3' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein Q, R1, R4, m and Ar are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 133
(2009/04/25)
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- A new efficient method for the total synthesis of linear furocoumarins
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A new efficient method for the synthesis of linear furocoumarins by a Nef reaction and intramolecular cyclocondensation in one pot results in the construction of a benzofuran ring. This method provides a new strategy to furnish the benzofuran framework easily, and also allows the convenient synthesis of furocoumarin derivatives with different substituents on the coumarin ring by a subsequent Pechmann reaction. This strategy has also been applied to the preparation of four additional benzofuran derivatives. Georg Thieme Verlag Stuttgart.
- Zhang, Bang-Le,Wang, Fang-Dao,Yue, Jian-Min
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p. 567 - 570
(2007/10/03)
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- Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists
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The present invention provides serotonergic aminoalkylbenzofurans of Formula (I): where R, R1, R2, R3, R4, R4′, R5, R5′, and R12 are as described in the specification.
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Page/Page column 21
(2010/11/08)
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- THIADIAZOLES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of Formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and ischemia reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of Formula (IA).
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Page/Page column 209
(2010/02/12)
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- ISOTHIAZOLE DIOXIDES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of the formula (IA): and the pharmaceutically acceptable salts and solvates thereof. D and E are different groups wherein one is N and the other is CR50. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of formula IA.
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Page/Page column 203
(2010/02/13)
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- An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans
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Twelve substituted benzofurans were synthesized from their corresponding substituted 1-allyl-2-allyloxybenzenes using ruthenium-mediated C- and O-allyl isomerization followed by ring-closing metathesis.
- Van Otterlo, Willem A.L.,Morgans, Garreth L.,Madeley, Lee G.,Kuzvidza, Samuel,Moleele, Simon S.,Thornton, Natalie,De Koning, Charles B.
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p. 7746 - 7755
(2007/10/03)
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- AZOLIDINONE-VINYL FUSED-BENZENE DERIVATIVES
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The present invention is related to azolidinedione-vinyl fused-benzene derivatives of formula (I) for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, graft rejection or lung injuries. Formula (I), wherein A, X, Y, Z, R1 , R2 and n are as described in the description.
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- THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).
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Page 239-240
(2008/06/13)
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- 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
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There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.
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- 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
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There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.
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- SEROTONERGIC BENZOFURANS
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The present invention provides serotonergic benzofurans of Formula (I): where A, R, R, R, R, and R are as described in the specification.
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Page/Page column 16
(2010/02/04)
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- BENZOFURYLPIPERAZINES AND BENZOFURYLHOMOPIPERAZINES: SEROTONIN AGONISTS
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The present invention provides serotonergic benzofurylpiperazines of Formula I: where: A is a piperazine of formula: and R, R1, R2, R3, R4, R5, R5', R6, R6', R7, R7', R8, and R8' are as described in the specification.
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- The synthesis and transition temperatures of 2-(4-alkyl- and 4-alkoxy-phenyl)-5-cyano-1-benzofurans and related diaryl-1-benzofurans - An assessment of how deviations from linearity and conformational effects in a core unit affect mesogenicity
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The synthesis and transition temperatures are reported for several 2-(4-alkyl- and 4-alkoxy-phenyl)-5-cyano-1-benzofurans, 2-(4′-alkylbiphenyl-4-yl)-5-cyano- and 5-(4′-alkylbiphenyl-4-yl)-2-cyano-1-benzofurans, and for compounds with other combinations of terminal alkyl and cyano groups in 2,5-disubstituted-1-benzofurans containing two phenyl units, some isolated examples of related cyclohexane systems are also presented. The mesogenic behaviour of these compounds and several intermediates (e.g. amides, acids and esters) is discussed and the transition temperatures are rationalised on the following basis (a) 1-benzofuran is a superior core unit to benzene, (b) 2,5-disubstitution in 1-benzofuran gives a bent core which adversely affects mesogenicity, to an extent which depends on its position in the core, (c) antiparallel associations in terminal cyano compounds can eliminate the disadvantage of a bent core structure, (d) 2-aryl-1-benzofurans have negligible inter-annular twist but 5-aryl-1-benzofurans have similar inter-annular twist to that in biphenyls.
- Friedman,Toyne,Goodby,Hird
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p. 2759 - 2772
(2007/10/03)
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- PYRROLO-PYRIDINE DERIVATIVES
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Compounds of formula I are ligands for dopamine receptor subtypes within the body and are therefore useful in the treatment and/or prevention of disorders of the dopamine system, in particular schizophrenia. STR1 wherein Q is STR2
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- One-step transformation of 2- or 3-(1-hydroxyalkyl) -2,3-dihydrobenzofurans to the acylbenzofurans with N-bromosuccinimide
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The one-step transformation of 2- or 3-(1-hydroxyalkyl)-2, 3-dihydrobenzofurans (1 or 2) to the 2- or 3-acylbenzofurans (5 or 6) with N-bromosuccinimide was performed with good yields. The reaction is characterized to take place via the continuous bromina
- Suzuki, Hideaki,Tsutsui, Hideyuki,Kano, Atsuyuki,Katoh, Satoru,Morita, Tadashi,Matsuda, Kiyoshi,Iibuchi, Norihiro,Ogawa, Masashi
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p. 1657 - 1661
(2007/10/03)
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- Potent and selective non-benzodioxole-containing endothelin-A receptor antagonists
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The benzodioxole ((methylenedioxy)benzene) group is present in a number of endothelin (ET) receptor antagonists thus far reported. As part of our own endothelin antagonist program we have developed (2R*,3R*,4S*)-1-(N,N- dibutylacetamido)-4-(1,3-benzodioxol-5-yl)-2-(4-methoxyphenyl)pyrrolidine-3- carboxylic acid (A-127722). This is a potent antagonist, binding to the ET(A) and ET(B) receptor subtypes with affinities (IC50) of 0.4 and 520 nM, respectively, and also contains the aforementioned benzodioxole. While this compound was seemingly optimized at its N-terminus, no effort had been directed toward understanding the contributions to binding affinity or receptor subtype selectivity conferred by the benzodioxole. Substitution by 1- or 2-naphthyl yielded weak antagonists. Oxygenated benzenes, such as p- anisyl, were potent compounds with IC50s in the low-nanomolar range. Simple deletion of either of the two oxygen atoms (dihydrobenzofurans) yielded extremely potent agents, possessing subnanomolar affinity for the ET(A) receptor. Additionally, the compounds showed enhanced selectivity, binding to the ET(B) receptor subtype in the micromolar range. This paper describes the development of this novel class of compounds.
- Tasker, Andrew S.,Sorensen, Bryan K.,Jae, Hwan-Soo,Winn, Martin,Von Geldern, Thomas W.,Dixon, Douglas B.,Chiou, William J.,Dayton, Brian D.,Calzadila, Samuel,Hernandez, Lisa,Marsh, Kennan C.,WuWong, J. Ruth,Opgenorth, Terry J.
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p. 322 - 330
(2007/10/03)
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