- p-TsOH mediated solvent and metal catalyst free synthesis of nitriles from aldehydes via Schmidt reaction
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A new and efficient protocol for the conversion of aldehyde into nitriles by modified Schmidt reaction. The reaction is carried out under solvent free condition using sodium azide as a source of nitrogen and catalysed by p-toluene sulphonic acid in presence of silica surface with no side product. This transformation gives good to excellent yield for numerous aromatic, aliphatic and heterocyclic nitriles using very simple reagent. This method has avoided the use of transition metal catalyst, toxic cyanide, hazardous solvent and offers a greener, simple and environment friendly procedure.
- Mitra, Bijeta,Pariyar, Gyan Chandra,Singha, Rabindranath,Ghosh, Pranab
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supporting information
p. 2298 - 2301
(2017/05/19)
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- FeCl3-silica: A green approach for the synthesis of nitriles from oximes
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A green and suitable protocol for the conversion of aldoximes into nitriles is described. The transformation is carried out under solvent-free conditions using FeCl3-silica medium. The protocol offers a green, single-step facile procedure with the use of less toxic metal salt to isolate nitriles in good to excellent yields.
- Ghosh, Pranab,Pariyar, Gyan Chandra,Saha, Bittu,Subba, Raju
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supporting information
p. 685 - 691
(2016/06/08)
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- Fe3O4-nanoparticles catalyzed an efficient synthesis of nitriles from aldehydes
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Fe3O4-CTAB NPs have been applied as a competent catalyst for one-pot synthesis of nitriles directly from aldehydes. The present investigation describes the synthesis of nitriles by combination of aromatic/aliphatic/heterocyclic aldehydes and hydroxylamine hydrochloride in the presence of iron oxide nanocatalyst in DMF under reflux condition. Fe3O4-CTAB NPs were prepared by reported method and characterized by FE-SEM, TEM, and XRD analysis. The amount of Fe in Fe3O4-CTAB was quantified by Atomic Absorption Spectroscopy (AAS). The protocol endow with excellent yield of products along with simple reaction set up and economically adept alternative approach.
- Ghosh, Pranab,Saha, Bittu,Pariyar, Gyan Chandra,Tamang, Abiral,Subba, Raju
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supporting information
p. 3618 - 3621
(2016/07/21)
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- FeCl3 mediated one-pot route to nitriles
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A new and convenient protocol for the transformation of aldehydes into nitriles using hydroxylamine hydrochloride by iron III chloride is presented. The protocol offers a very simple, cost efficient, and environmentally benign procedure with good to excellent yield of nitrile.
- Ghosh, Pranab,Subba, Raju
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supporting information
p. 4885 - 4887
(2013/08/28)
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- Chemoselective Schmidt reaction mediated by triflic acid: Selective synthesis of nitriles from aldehydes
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An excellent utility of Schmidt reaction of aldehydes to access corresponding nitriles in an instantaneous reaction is demonstrated. The reaction of aldehydes with NaN3 and TfOH furnishes the corresponding nitriles in near quantitative yields and tolerates a variety of electron-withdrawing and electron-donating substituents on the substrates. Formanilides, a common side product in Schmidt reaction, is not observed in this reaction. Besides these advantages, the salient feature of this reaction is that it exhibits a remarkable chemoselectivity, as acid and ketone functionalities are well tolerated under the reaction conditions. The reaction is easily scalable, high yielding, and nearly instantaneous.
- Rokade, Balaji V.,Prabhu, Kandikere Ramaiah
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experimental part
p. 5364 - 5370
(2012/09/07)
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- A general and convenient route to oxazolyl ligands
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A diverse range of chiral and achiral oxazolyl ligands, which have many applications including catalysis and luminescent devices, are synthesized simply in three steps from readily available and inexpensive phenol and amino alcohol starting materials. The method can be applied to ligands with electron-donating/-withdrawing and sterically demanding/undemanding substituents, and can conveniently be scaled up to >25 g of product.
- Aspinall, Helen C.,Beckingham, Oliver,Farrar, Michael D.,Greeves, Nicholas,Thomas, Christopher D.
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supporting information; experimental part
p. 5120 - 5123
(2011/10/19)
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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 68
(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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- 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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- Use of chromans
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The invention relates to the use of 2-[4-({[(2R)-8-isopropoxy-chroman-2-yl]-methyl}amino)butyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide, its physiologically acceptable salts, hydrates and/or solvates, in particular its hydrochloride, for the production o
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- Synthesis and analgesic activity of some 1-benzofurans, 1-benzothiophenes and indoles
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3-Unsubstituted 1-benzofurans 1e and 1f, 3-methyl-1-benzofurans 1a-1d, and 3-amino-1-benzofurans 2a-21, as well as 3-amino-1-benzothiophenes 3a, 3b and 3-aminoindoles 4a-4f, 11a, and 11b were prepared and tested as analgesics. The 3-amino-1-benzofurans 2 were prepared from the corresponding 2-hydroxybenzonitriles 5 and phenacyl bromides 6 via intermediates 7. Similar treatment of 2-sulfanylbenzonitrile (8) provided 3-amino-1-benzothiophenes 3. Appropriately substituted 2-aminobenzonitriles 9 then provided N-substituted 3-aminoindoles 4. 1-(Ethoxycarbonyl)indoles 4e and 4f were successfully deprotected giving indoles 11a and 11b, respectively.
- Radl, Stanislav,Hezky, Petr,Urbankova, Jitka,Vachal, Petr,Krejci, Ivan
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p. 280 - 296
(2007/10/03)
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- Desazadesmethyldesferrithiocin analogues as orally effective iron chelators
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Further structure-activity studies of desferrithiocin analogues are carried out. (S)-Desazadesmethyldesferrithiocin, 2-(2-hydroxyphenyl)-Δ2- thiazoline-4(S)-carboxylic acid, serves as the principal framework in the current paper. Desazadesmethyldesferrithiocin can be structurally altered with facility, and data are already available on its iron-clearing properties and toxicity parameters. Four different kinds of structural modifications of this framework are undertaken: introduction of hydroxy, carboxy, or methoxy groups on the aromatic ring; alteration of the thiazoline ring; increasing the distance between the ligand donor atoms; and benz-fusion of the aromatic rings. The structural modifications described are shown to have a tremendous impact on both the iron clearance and toxicity profiles of the desazadesmethyldesferrithiocin molecule. All of the compounds are assessed in a bile-duct-cannulated rodent model to determine iron clearance efficiency. Ligands which demonstrate an efficiency of greater than 2% are carried forward to the iron-overloaded primate for iron-clearing measurements. Ligands with efficiencies greater than 3% in the primate are then evaluated in a formal toxicity study in rodents. On the basis of the results of the present work, 2-(2,4-dihydroxyphenyl)-Δ2-thiazoline-4(S)-carboxylic acid is a promising candidate for clinical evaluation.
- Bergeron, Raymond J.,Wiegand, Jan,Weimar, William R.,Vinson, J. R. Timothy,Bussenius, J?rg,Yao, Guo Wei,McManis, James S.
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- 8,2'-DIHYDROXYFLAVONE FROM PRIMULA PULVERULENTA
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A novel flavone, isolated from the farinose exudate of Primula pulverulenta, was identified as 8,2'-dihydroxyflavone.This is the first naturally occurring flavone, in which ring A is oxygenated only at C-8.The structure was deduced from spectral comparisons with the structurally related flavones: 5,2'-, 3,2'- and 2',3'-dihydroxyflavone and confirmed by total synthesis.The spectral properties of other flavones oxygenation with a simple pattern are discussed in relation to 8,2'-dihydroxyflavone.Key Word Index - Primula pulverulenta; Primulaceae; farinose excretion; 8,2'-dihydroxyflavone; 8,2'-dimethoxyflavone.
- Wollenweber, Eckhard,Mann, Karin,Iinuma, Munekazu,Tanaka, Toshiyuki,Mizuno, Mizuo
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p. 1483 - 1486
(2007/10/02)
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- 7-Substituted Benzothiophenes and 1,2-Benzisothiazoles. Part 1. Hydroxy- or Methoxy-derivatives
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Readily available 2-hydroxy-3-methoxybenzaldehyde (orthovanilin) is converted, via terminal rearrangement (Newman-Kwart) of the O-aryl-NN-dimethylthiocarbamate, into 2-mercapto-3-methoxybenzaldehyde (3).This thiol undergoes base-catalysed condensation wit
- Rahman, Loay K. A.,Scrowston, Richard M.
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p. 2973 - 2978
(2007/10/02)
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