- Lewis Acid-Mediated Cyanation of Phenols Using N-Cyano-N-phenyl-p-toluenesulfonamide
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Lewis acid-mediated cyanation of phenol derivatives with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) has been developed. The reaction proceeded efficiently with high regioselectivity to produce aromatic nitriles in moderate to excellent yields, which provides a direct and practical access to valuable products. (Figure presented.).
- Zhang, Wu,Li, Tao,Wang, Qingli,Zhao, Wanxiang
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supporting information
p. 4914 - 4918
(2019/11/03)
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- Chromatography-free entry to substituted salicylonitriles: Mitsunobu-triggered domino reactions of salicylaldoximes
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A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the
- Whiting, Ellis,Lanning, Maryanna E.,Scheenstra, Jacob A.,Fletcher, Steven
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p. 1229 - 1234
(2015/01/30)
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- Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles
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The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.
- Nimnual, Phongprapan,Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
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supporting information
p. 8657 - 8667
(2015/09/15)
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- HCV PROTEASE INHIBITORS
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The present invention discloses a compound of general formula (I); A is O, S, CH, NH or NR', when O links with Z3, Z1 is N or CRZ1, Z2 is CRZ2, when Z1 links with O, Z2 is CH, Z3 is C-Ar; Ra, Rb, Rc and Rd independently is H, OH, halogen or -Y1-Rm; A1 is NH or CH2; R1' is alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl; A2 is N, O or linking bond; R1 is hydrogen, or, R1 linking covalently with R3 forms C5-C9 saturated or unsaturated hydrocarbon chain substituted by O or N; R3 is alkyl, cycloalkyl, heterocycloalkyl, alkyl substituted by cycloalky etc; R4 is alkoxy-CO, alkyl-NHCO, (alkyl)2NCO, or formyl substituted by aryl, cycloalkyl, heterocycloalkyl.
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Paragraph 0041
(2014/06/24)
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- HCV Protease Inhibitors
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A compound of general formula (I); A is O, S, CH, NH or NR′, when O links with Z3, Z1 is N or CRZ1, Z2 is CRZ2, when Z1 links with O, Z2 is CH, Z3 is C—Ar; Ra, Rb, Rc and Rd independently is H, OH, halogen or —Y1—Rm; A1 is NH or CH2; R1′ is alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl; A2 is N, O or linking bond; R1 is hydrogen, or, R1 linking covalently with R3 forms C5-C9 saturated or unsaturated hydrocarbon chain substituted by O or N; R3 is alkyl, cycloalkyl, heterocycloalkyl, alkyl substituted by cycloalkyl etc; R4 is alkoxy-CO, alkyl-NHCO, (alkyl)2NCO, or formyl substituted by aryl, cycloalkyl, heterocycloalkyl.
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Paragraph 0105; 0107-0109
(2014/06/24)
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- Facile one-pot transformation of phenols into o-cyanophenols
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The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.
- Nakai, Yuhta,Moriyama, Katsuhiko,Togo, Hideo
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p. 6077 - 6083
(2015/03/30)
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- A catalytic route to ampakines and their derivatives
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A catalytic domino reaction that efficiently provides access to an important class of heterocycles, the ampakines, is reported. Our approach is based on the cobalt-catalyzed hydroformylation of dihydrooxazines and allows for the facile synthesis of the pharmaceutically interesting compound CX-614 and related substances.
- Mulzer, Michael,Coates, Geoffrey W.
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supporting information; experimental part
p. 1426 - 1428
(2011/05/04)
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- BENZOFUROPYRIMIDINONES AS PROTEIN KINASE INHIBITORS
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A compound according to formula I: or a pharmaceutically acceptable salt thereof; wherein R1, R2, R3a, R3b, R3c and R3d are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.
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Page/Page column 202-203
(2009/08/14)
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- Synthesis and biological evaluation of 2-(3′,4′,5′-trimethoxybenzoyl)-3-N,N-dimethylamino benzo[b]furan derivatives as inhibitors of tubulin polymerization
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Molecules that target microtubules have an important role in the treatment of cancer. A new class of inhibitors of tubulin polymerization based on the 2-(3,4,5-trimethoxybenzoyl)-2-dimethylamino-benzo[b]furan molecular skeleton was synthesized and evaluat
- Romagnoli, Romeo,Baraldi, Pier Giovanni,Sarkar, Taradas,Carrion, Maria Dora,Cruz-Lopez, Olga,Lopez Cara, Carlota,Tolomeo, Manlio,Grimaudo, Stefania,Di Cristina, Antonietta,Pipitone, Maria Rosaria,Balzarini, Jan,Gambari, Roberto,Ilaria, Lampronti,Saletti, Roberto,Brancale, Andrea,Hamel, Ernest
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body text
p. 8419 - 8426
(2009/04/11)
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- CARBAMOYL-TYPE BENZOFURAN DERIVATIVES
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The present invention provides a carbamoyl-type benzofuran derivative of the formula [1]: wherein Ring Z is a group of the formula: etc.; A is a single bond, and the like; Y is a cycloalkanediyl group, etc.; R4 and R5 are the same or different and each is an optionally substituted lower alkyl group, etc.; R1 is a halogen atom, etc.; Ring B of the formula: is an optionally substituted benzene ring; and R3 is a hydrogen atom, etc., or a pharmaceutically acceptable salt thereof, which is useful as an FXa inhibitor.
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Page/Page column 67
(2008/06/13)
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- NOVEL BENZOFURAN DERIVATIVE, MEDICINAL COMPOSITION CONTAINING THE SAME, AND USES OF THESE
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[From equivalent EP1710233A1] The present invention provides compounds represented by general formula (I): or pharmaceutical acceptable salts thereof, wherein R1 is hydrogen or lower alkyl; R2 is lower alkyl, halo-lower alkyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, arylalkenyl, aryloxy-lower alkyl, heteroaryl, heteroaryl-lower alkyl, etc; R3, R4, R5 and R6 are each hydrogen, halogen, cyano, lower alkyl, halo-lower alkyl, lower alkoxy, hydroxy, aryl, etc; provided that at least one of R3, R4, R5 and R6 is other than hydrogen. Compound (I) of the present invention shows a potent adenosine A2A receptor antagonistic activity, and are useful for treating or preventing a disease mediated by adenosine A2A receptors such as motor function disorders, depression, anxiety disorders, cognitive function disorders, cerebral ischemia disorders, restless legs syndrome and the like.
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Page/Page column 22
(2008/06/13)
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- COMPOUNDS WITH MIXED PDE-INHIBITORY AND β-ADRENERGIC ANTAGONIST OR PARTIAL AGONIST ACTIVITY FOR TREATMENT OF HEART FAILURE
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This invention provides compounds that possess inhibitory activity against β--adrenergic receptors and phosphodiesterase PDE, including phosphodiesterase 3 (PDE3 ). This invention further provides pharmaceutical compositions comprising such -compounds; methods of using such compounds for treating cardiovascular disease, stroke, epilepsy, ophthalmic disorder or migraine; and methods of preparing pharmaceutical compositions and compounds that possess inhibitory activity against ?-adrenergic receptors and PDE.
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- BENZOFURAN DERIVATIVE
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The present invention provides a benzofuran derivative of the formula [1]: wherein x is a group of the formula: -N="or" -CH=; Y is an optionally substituted amino group, an optionally substituted cycloalkyl group or an optionally substituted saturated heterocyclic group; A is a single bond, a carbon chain optionally having a double bond within or at the end(s) of the chain, or an oxygen atom; R1 is a hydrogen atom or a halogen atom; Ring B is an optionally substituted benzene ring; and R3 is a hydrogen atom, or a pharmaceutically acceptable salt thereof, which is useful as a medicament, especially as an activated blood coagulation factor X inhibitor.
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- On the magnitude and specificity of medium effects in enzyme-like catalysts for proton transfer
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Medium effects are normally studied by comparing the rates of reactions in different solvents. However, medium effects at the active site of enzymes differ dramatically from bulk solvents, both in their diversity (the presence of more than one type of "so
- Hollfelder,Kirby,Tawfik
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p. 5866 - 5874
(2007/10/03)
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- The role of the hydrogen bonding in cycloadditions of benzonitrile oxide with cyanophenols
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The reactivity of aromatic nitriles in cycloadditions with benzonitrile oxide is remarkably enhanced by the ortho-hydroxy substituent. Semiempirical PM3 calculations are in agreement with a hydrogen bonding effect.
- Corsaro, Antonino,Buemi, Giuseppe,Chiacchio, Ugo,Perrini, Giancarlo,Pistara, Venerando,Romeo, Roberto
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p. 7885 - 7892
(2007/10/03)
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- TEMPLATE HOUBEN-HOESCH REACTION ON METAL PHENOLATES. SYNTHESIS OF AROMATIC KETONES, NITRILES AND AMIDES. CRYSTAL STRUCTURE OF DICHLORO-BORON
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The crystal structure of dichloro-boron (6dx) establishes for the first time the coordination mechanism of the ortho-selective reaction of metal phenolates and nitriles.Crystal data: chemical formula C9H7BCl5NO2; a = 11.743(2), b = 13.390(2), c = 8.765(3) Angstroem, β = 99.71(2) deg; space group P21/n.Variously substituted aromatic ketones, nitriles and amides have been obtained in a "one-pot" reaction.
- Bigi, Franca,Maggi, Raimondo,Sartori, Giovanni,Casnati, Giuseppe,Bocelli, Gabriele
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p. 283 - 289
(2007/10/02)
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- Pyridine derivatives
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The invention concerns novel, pharmaceutically useful 1,3-dioxane alkenoic acid derivatives of the formula I containing a pyridyl moiety at position 4 of the dioxane ring and in which the groups at positions 2, 4 and 5 have cis-relative stereochemistry, X is hydrogen, alkoxy or hydroxy, Y is vinylene, n is 1 or 2, A1 is alkylene, the substituents R1 and R2 at position 2 of the dioxane ring have a variety of values defined hereinafter, and R4 is hydroxy, a physiologically acceptable alcohol residue or alkanesulphonamido, and the pharmaceutically acceptable salts thereof. The invention also includes processes for the manufacture and use of the acid derivatives as well as pharmaceutical compositions for therapeutic use in one or more of a variety of diseases such as ischaemic heart disease, cerebrovascular disease, asthmatic disease and/or inflammatory disease.
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- EXLUSIVE ORTHO CYANATION AND ALKYLTHIOCARBONYLATION OF ANILINES AND PHENOLS USING BORON TRICHLORIDE
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Use of boron trichloride with or without an aditional Lewis acid makes possible a one-step synthesis of 2-cyano and 2-alkylthiocarbonyl anilines and phenols.
- Adachi, Makoto,Sugasawa, Tsutomu
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