- Oxidative nucleophilic substitution of hydrogen in nitrobenzene with 2-phenylpropionitrile carbanion and potassium permanganate oxidant
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The carbanion of 2-phenylpropionitrile adds to nitrobenzene in the p-position in liquid ammonia to give the relative stable σH-adduct which is oxidised with KMnO4 to 2-phenyl-2-(4-nitrophenyl)propionitrile; the relationships of rates of various reactions in these systems are estimated.
- Makosza, Mieczyslaw,Stalinski, Krzysztof,Klepka, Cezary
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Read Online
- Nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O: Observation of unexpected regioselectivity
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We describe the nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O to afford a variety of α-amino-α,β-unsaturated esters with high regioselectivities. The selective α-carboxylation of ynamides with this catalytic protocol is unexpected in view of the electronic bias of ynamides and is in sharp contrast to our previous study in which a stoichiometric amount of Ni(0) was used to form a β-carboxylated product exclusively. We revealed that this unexpected C-C bond formation was induced by the combination of Zn and MgBr2.
- Doi, Ryohei,Abdullah, Iman,Taniguchi, Takahisa,Saito, Nozomi,Sato, Yoshihiro
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Read Online
- Reversible addition of carbon nucleophiles to some nitrogen-substituted η6-arenetricarbonylchromium(0) compounds
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A study has been made of the nucleophilic addition/oxidation reactions of η6-1-methyl-1,2,3,4-tetrahydroquinolinetricarbonylchromium(0) (1), η6-1-methylindolinetricarbonylchromium(0) (2), and η6-2-N,N-dimethylaminotoluenetricarbonylchromium(0) (3) with the nucleophiles 2-lithio-2-methyl-propionitrile (A), 2-lithio-acetonitrile (B) and 2-lithio-2-methyl-1,3-dithiane (C).The regioselectivity in the addition of stabilized nucleophiles is time- and temperature-dependent, indicating the onset of thermodynamic control in prolonged/high temperature reactions.The addition is reversible, as indicated by crossover experiments with benzene-Cr(CO)3, the rate for dissociation of the C-C bond being strongly dependent on both the structure of the intermediate η5-cyclohexadienyltricarbonylchromium anions as well as the structure of the nucleophile.The regioselectivity of the addition/oxidation reaction can be optimized by an appropriate choice of reaction for each of the compounds 1, 2 and 3.
- Ohlsson, Bengt,Ullenius, Christina
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Read Online
- Synthesis of indolines by copper-mediated intramolecular aromatic C-H amination
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A Cu(OAc)2-mediated intramolecular aromatic C-H amination proceeds with the aid of a picolinamide-type bidentate coordination group to deliver the corresponding indolines in good yields. The reaction occurs smoothly even under noble-metal-free conditions, and in some cases the use of an MnO2 terminal oxidant renders the process catalytic in Cu. The mild oxidation aptitude of Cu(OAc)2 and/or MnO2 accommodates the formation of electron-rich thiophene-and indole-fused indoline analogues. The Cu-based system can provide an effective approach to various indolines of potent interest in pharmaceutical and medicinal chemistry.
- Takamatsu, Kazutaka,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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Read Online
- Palladium-Catalyzed Distal m-C-H Functionalization of Arylacetic Acid Derivatives
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Herein, we present m-C-H olefination on derivatives of phenylacetic acids by tethering with a simple nitrile-based template through palladium catalysis. Notably, the versatility of the method is evaluated with a wide range of phenylacetic acid derivatives for obtaining the meta-olefination products in fair to excellent yields with outstanding selectivities under mild conditions. Significantly, the present strategy is successfully exemplified for the synthesis of drugs/natural product analogues (naproxen, ibuprofen, paracetamol, and cholesterol).
- Srinivas, Dasari,Satyanarayana, Gedu
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supporting information
p. 7353 - 7358
(2021/10/01)
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- Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
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Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
- Utsumi, Tatsuki,Noda, Kenta,Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 3583 - 3588
(2020/08/05)
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- Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions
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The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.
- Chan, Kaai-Tung,Che, Chi-Ming,Du, Lili,Liu, Yungen,Phillips, David Lee,To, Wai-Pong,Tong, Glenna So Ming,Wu, Liang-Liang,Yu, Daohong
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p. 6370 - 6382
(2020/07/15)
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- Synthesis of Tertiary Benzylic Nitriles via Nickel-Catalyzed Markovnikov Hydrocyanation of α-Substituted Styrenes
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The Markovnikov hydrocyanation of α-substituted styrenes enables the synthesis of tertiary benzylic nitriles under nickel catalysis. The Lewis-acid-free transformation features an unprecedented functional groups tolerance, including the-OH and-NH2 groups. A broad range of tertiary benzylic nitriles were obtained in good to excellent yields. In addition, an asymmetric version of this reaction was preliminarily investigated.
- Xing, Yidan,Yu, Rongrong,Fang, Xianjie
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p. 1008 - 1012
(2020/02/04)
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- Cobalt-catalyzed C[sbnd]H activation/C[sbnd]O formation: Synthesis of benzofuranones
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Herein, C[sbnd]H activation/C[sbnd]O formation reaction using novel cobalt catalytic system is reported. This reaction was given benzofuranones in moderate to excellent yields at room-temperature under air reaction conditions. The introduced strategy is efficient and low-cost method to synthesized benzofuranones from α,α-disubstitution acetic acid.
- Hajipour, Abdol R.,Khorsandi, Zahra
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- Asmic Isocyanide-Nitrile Isomerization-Alkylations
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Anisylsulfanylmethylisocyanide, Asmic, is a versatile building block whose alkylations provide a range of substituted isocyanides. The anisylsulfanyl group plays a critical role in the sequenced deprotonation-alkylation and the subsequent sulfanyl-lithium exchange. Complexation of the anisylsulfanyl group to BuLi in the presence of TMEDA affords a lithiated isocyanide whose alkylations generate trisubstituted isocyanides. In the absence of TMEDA, BuLi triggers cyanide expulsion to afford a transient carbene; reorientation of cyanide with attack at the carbene affords a lithiated nitrile whose alkylations afford quaternary nitriles. The complexation-induced isocyanide-nitrile rearrangement is exceptionally facile, occurring within 5 min at –78 °C. Detailed mechanistic and computational analyses identify the importance of chelation in the bifurcating mechanism: internal chelation favors cyanide extrusion to form a carbene whereas chelating agents favor arylsulfanyl-lithium exchange to generate a lithiated isocyanide. The combined experimental and computational analyses reveal a new mechanism for isocyanide-nitrile isomerization which provides valuable insight for rapidly assembling substituted isocyanides.
- Alwedi, Embarek,Lujan-Montelongo, J. Armando,Cortés-Mejía, Rodrigo,del Campo, Jorge M.,Altundas, Bilal,Fleming, Fraser F.
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supporting information
p. 4644 - 4648
(2019/07/31)
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- OXIDATIVE CONVERSION OF ALIPHATIC ALDEHYDES TO NITRILES USING OXOAMMONIUM SALT
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The present invention relates to an oxidative transformation method of aliphatic benzaldehydes to nitriles using NH_4OAc through oxoammonium salts. By using stoichiometric amounts of oxoammonium salts to establish optimal reaction conditions associated with the oxidative conversion of aliphatic benzaldehydes to nitriles, high yields of nitrile can be selectively obtained, and the oxoammonium salts used can be oxidized and reused in a simple method.COPYRIGHT KIPO 2020
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Paragraph 0055-0063; 0136-0142
(2019/12/10)
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- Synthesis of Nitrile-Bearing Quaternary Centers by an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy
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The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers by a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.
- Alazet, Sébastien,West, Michael S.,Patel, Purvish,Rousseaux, Sophie A. L.
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supporting information
p. 10300 - 10304
(2019/07/04)
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- Surprising and Highly Efficient Use of Methylmagnesium Chloride as a Non-Nucleophilic Base in the Deprotonation and Alkylation of sp3 Centres Adjacent to Nitriles
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Methylmagnesium chloride (MeMgCl) is a key reagent in research and industry typically as a nucleophile. In this article we develop the use of MeMgCl as a non-nucleophilic base in conjunction with catalytic amounts of an amine mediator. Specifically, we use the base to deprotonate α to a variety of nitriles in alkylation reactions, applying it to the synthesis of a wide variety of tertiary and quaternary nitriles, including examples where we successively and successfully added three different substituents on the carbon α to the nitrile. This method is generally applicable, high yielding and much greener than existing methods, and it has considerable advantages for industrial application.
- Gbadebo, Omolola,Smith, Dennis,Harnett, Ger,Donegan, Gregory,O'Leary, Patrick
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p. 7037 - 7045
(2019/01/04)
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- Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate
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An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.
- Kim, Myeong Jin,Mun, Junyoung,Kim, Jinho
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supporting information
p. 4695 - 4698
(2017/11/17)
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- Synthetic method of fexofenadine intermediate
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The invention provides a synthetic method of a fexofenadine intermediate 2-[4-[4-[4-(hydroxybenzhydryl)-1-piperidyl]-butyryl]phenyl]-2- methylmethacrylate. The method comprises the following steps: methylation of phenylacetonitrile which is used as a raw material, basic hydrolysis, weinreb amidation reaction, Friedel-crafts reaction, acid hydrolysis, esterification and condensation. The method has the following advantages: raw materials and auxiliary materials are cheap and easily available; yield is high; cost is low; there is no meta-isomer; and the method is suitable for industrial production.
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Paragraph 0010; 0032; 0033; 0034; 0035; 0036
(2017/02/28)
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- Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes
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1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield. (Figure presented.).
- Bucher, Janina,Wurm, Thomas,Taschinski, Svenja,Sachs, Eleni,Ascough, David,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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supporting information
p. 225 - 233
(2017/02/05)
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- Five-membered urea link and coumarin derivative or its pharmaceutically acceptable salts and use
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The invention relates to a small molecule medicament based on PI3K (Phosphatidyl Inositol 3-kinase)/mTOR (Mammalian Target of Rapamycin) double targets, belongs to the technical field of chemical medicines, and in particular relates to a five-membered urea ring-coumarin derivative or a pharmaceutical salt and an application thereof. A compound claimed by the invention has a structure shown as formula I described in the specification, and pharmacological experiments show that the compound has excellent inhibitory activity in a plurality of tumor cell strains.
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Paragraph 0065; 0081; 0082
(2016/10/07)
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- Access to nitriles from aldehydes mediated by an oxoammonium salt
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A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.
- Kelly, Christopher B.,Lambert, Kyle M.,Mercadante, Michael A.,Ovian, John M.,Bailey, William F.,Leadbeater, Nicholas E.
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p. 4241 - 4245
(2015/04/14)
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- METHOD FOR PRODUCING NITRILE COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing a nitrile compound capable of obtaining a nitrile compound in a short time and at a low temperature, while maintaining a high yield. SOLUTION: There is provided a method for producing a nitrile compound using a compound having a hydroxymethylene group as a raw material. The nitrile compound is obtained by mixing and reacting an aliphatic compound or an aromatic compound having a hydroxymethylene group with a N-nitrosyl compound, an oxidant, an iodinating agent and ammonia water. COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0041-0044; 0047; 0051
(2016/11/17)
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- OXADIAZOLE COMPOUNDS
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The present invention relates to a compound of formula (I) or (II) or a stereoisomer, enantiomer, racemic, or tautomer thereof, (I) (II) wherein R1,R2,R3,L1,L2,L3,L4,L5 and n, have the same meaning as that defined in the claims and the description. The present invention also relates to compositions, in particular pharmaceuticals, comprising such compounds, and to uses of such compounds and compositions for the prevention and/or treatment of metabolic disorders and/or neurodegenerative diseases, and/or protein misfolding disorders.
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Page/Page column 142; 143
(2015/11/11)
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- Palladium(II)-catalyzed directed trifluoromethylthiolation of unactivated C(sp3)-H bonds
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The synthesis of trifluoromethylthiolated aliphatic acid derivatives by Pd-catalyzed C(sp3)-H bond functionalization was developed. Using a bidentate directing group, the direct and selective introduction of a SCF3 moiety was possible on a range of amides with remarkable selectivity for C(sp3)-centers with an electrophilic SCF3 source and pivalic acid as an additive. This work constitutes an example of the unactivated C(sp3)-SCF3 bond formation by C-H activation offering a new access to relevant molecules.
- Xiong, Heng-Ying,Besset, Tatiana,Cahard, Dominique,Pannecoucke, Xavier
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p. 4204 - 4212
(2015/05/05)
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- Synergistic effect of a bis(proazaphosphatrane) in mild palladium-catalyzed direct α-arylations of nitriles with aryl chlorides
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The effect of a bis(proazaphosphatrane) ligand on the palladium-catalyzed direct α-arylation of nitriles with various aryl chlorides under mild conditions is reported. Comparisons of the catalytic properties of this ligand with those of three related mono(proazaphosphatrane)s under the same reaction conditions revealed that bis(proazaphosphatrane) displayed a synergistically enhanced activity. In the presence of the bis(proazaphosphatrane) ligand, ethyl cyanoacetate and primary as well as secondary nitriles were efficiently coupled with a wide variety of aryl chlorides that contained electron-rich, electron-poor, and electron-neutral groups.
- Han Kim, So,Jang, Wonseok,Kim, Min,Verkade, John G.,Kim, Youngjo
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p. 6025 - 6029
(2015/03/30)
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- Palladium-catalyzed carbonylative α-arylation to β-ketonitriles
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A carbonylative α-arylation process employing unactivated nitriles for the first time is described. The reaction tolerates a range of (hetero)aryl iodides and several nitrile coupling partners. No prefunctionalization of the nitriles is necessary and the resulting β-ketonitriles are obtained in good to excellent yields. The methodology also allows for a convenient 13C-labelling of the generated carbonyl moiety. Three COmponent α-arylation: A carbonylative α-arylation process employing nitriles for the first time is described (see scheme). The reaction tolerates a range of (hetero)aryl iodides and several nitrile coupling partners. No prefunctionalization of the nitriles is necessary and the resulting β-ketonitriles are obtained in good to excellent yields. In addition, the methodology allows for a 13C-labelling of the generated carbonyl moiety.
- Schranck, Johannes,Burhardt, Mia,Bornschein, Christoph,Neumann, Helfried,Skrydstrup, Troels,Beller, Matthias
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supporting information
p. 9534 - 9538
(2014/08/18)
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- SPIRO-SUBSTITUTED OXINDOLE DERIVATIVES HAVING AMPK ACTIVITY
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The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.
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Page/Page column 112
(2015/01/07)
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- OLEFIN SUBSTITUTED OXINDOLES HAVING AMPK ACTIVITY
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The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.
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Page/Page column 107
(2015/01/07)
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- Simple one-pot conversion of alcohols into nitriles
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Various benzylic and primary alcohols were efficiently converted into the corresponding nitriles in good yields at room temperature by treatment with tert-butyl hypochlorite, diiodine, or 1,3-diiodo-5,5-dimethylhydantoin in the presence of (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (TEMPO), followed by treatment with diiodine and aqueous ammonia. The nitriles were obtained in good yields and high purities simply by extraction of the reaction mixture with chloroform and subsequent removal of the solvent.
- Shimojo, Hiroyuki,Moriyama, Katsuhiko,Togo, Hideo
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p. 2155 - 2164
(2013/08/23)
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- SUBSTITUTED TETRAHYDROISOQUINOLINE COMPOUNDS AS FACTOR XIA INHIBITORS
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The present invention provides compounds of Formula (I): or stereoisomers, pharmaceutically acceptable salts thereof, wherein all of the variables are as defined herein. These compounds are inhibitors of factor XIa and/or plasma kallikrein which may be used as medicaments.
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Paragraph 00352
(2013/04/25)
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- FURANOPYRIDINE CANNABINOID COMPOUNDS AND RELATED METHODS OF USE
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Furanopyridine cannabinoid analog compounds of the formula (I) are disclosed. The compounds are useful to modify the activity of CB 1 and CB2 receptors and treat conditions mediated by these receptors.
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Page/Page column 19
(2011/04/13)
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- FURANOPYRIMIDINE CANNABINOID COMPOUNDS AND RELATED METHODS OF USE
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Furanopyrimidine cannabinoid analog compounds of the formula I are disclosed. The compounds are useful to modify the activity of CB 1 and CB2 receptors and treat conditions mediated by these receptors.
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Page/Page column 20
(2011/04/13)
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- Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates
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Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright
- Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei
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supporting information; experimental part
p. 4470 - 4474
(2011/06/24)
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- Generation of iminyl copper species from α-azido carbonyl compounds and their catalytic C-C bond cleavage under an oxygen atmosphere
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Figure presented A copper-catalyzed reaction of α-azidocarbonyl compounds under an oxygen atmosphere is reported where nitriles are formed via C-C bond cleavage of a transient iminyl copper intermediate. The transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from α-azidocarbonyl compounds and their C-C bond cleavage, where molecular oxygen (1 atm) is a prerequisite to achieve the catalytic process and one of the oxygen atoms of O2 was found to be incorporated into the β-carbon fragment as a carboxylic acid.
- Chiba, Shunsuke,Zhang, Line,Ang, Gim Yean,Hui, Benjamin Wei-Qiang
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supporting information; experimental part
p. 2052 - 2055
(2010/07/04)
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- Lithium naphthalenide-induced reductive alkylation and addition of aryl-and heteroaryl-substituted dialkylacetonitriles
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Lithium naphthalenide (LN)-induced reductive alkylation/addition reactions of aryl-, pyridyl-, and 2-thienyl-substituted dialkylacetonitriles have been investigated. Upon treatment with LN in THF at -40°C, both aryl and pyridyl precursors could undergo the reductive decyanation smoothly, and the in situ generated carbanions could be readily trapped by alkyl halides, ketones, aldehydes, or even oxygen to afford a wide range of functionalized aromatic derivatives bearing a newly established quaternary carbon. To effect the desired reductive alkylation of 2-thienyldialkylacetonitriles, a much lower temperature such as -100°C was required. Also with these substrates, an interesting ring-opening/S-alkylation process was observed when the reductive alkylation were performed at -78°C to give 1-alkylsulfanyl-1,3,4-trienes. A mechanistic discussion is given for this observation.
- Tsao, Jing-Po,Tsai, Ting-Yueh,Chen, I-Chia,Liu, Hsing-Jang,Zhu, Jia-Liang,Tsao, Sheng-Wei
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scheme or table
p. 4242 - 4250
(2011/02/25)
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- Pyrimidine Classical Cannabinoid Compounds and Related Methods of Use
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Disclosed are compounds of the formula I: wherein R1, R2, V, W, X, Y and Z can be as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors.
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Page/Page column 6
(2009/12/05)
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- Pyrimidine Non-Classical Cannabinoid Compounds and Related Methods of Use
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Disclosed are compounds of the formula I: wherein R1, R2, V, W, X, Y and Z can be as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors.
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Page/Page column 6
(2009/12/05)
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- Pyridine Classical Cannabinoid Compounds and Related Methods of Use
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Disclosed are compounds of the formula I: wherein R1, R2, V, W, X, Y and Z can be as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors.
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Page/Page column 6
(2009/12/05)
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- Pyridine Non-Classical Cannabinoid Compounds and Related Methods of Use
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wherein R1, R2, V, W, X, Y and Z can be as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors.
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Page/Page column 8
(2009/12/05)
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- TRP-M8 RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS
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Tetrahydroisoquinoline compounds of formula (I), and compositions containing them, for the treatment of acute, inflammatory and neurophatic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neurophatic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintened pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.
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Page/Page column 66
(2009/07/17)
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- Understanding the differential performance of Rh2(esp) 2 as a catalyst for C-H amination
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(Chemical Equation Presented) Catalytic amination of saturated C-H bondsis performed efficiently with the use of Rh2(esp)2. Efforts to identify pathways for catalyst degradation and/or arrest have revealed a singleelectron oxidation event that gives rise to a red-colored, mixed-valence dimer, [Rh2(esp)2]+. This species is fortuitously reduced by carboxylic acid, a byproductgenerated in the reaction cycle with each turnover of the diacyloxyiodi ne oxidant. These findings have led to the conclusion that the high performance of Rh2(esp)2 is due in part to the superior kinetic stability of its one-electron oxidized form relative to other dimeric Rh complexes.
- Zalatan, David N.,Bois, J. Du
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supporting information; experimental part
p. 7558 - 7559
(2009/10/17)
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- Metalated nitriles: Organolithium, -magnesium? and -copper exchange of α-halonitriles
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(Chemical Equation Presented) α-Halonitriles react with alkyllithium, organomagnesium, and lithium dimethylcuprate reagents generating reactive, metalated nitriles. The rapid halogen-metal exchange with alkyllithium and Grignard reagents allows selective exchange in the presence of reactive carbonyl electrophiles, including aldehydes, providing a high-yielding alkylation protocol. Lithiated and magnesiated nitriles react with propargyl bromide by SN2 displacement whereas organocopper nitriles react by S N2′ displacement, correlating with the formation of a C-metalated nitrile.
- Fleming, Fraser F.,Zhang, Zhiyu,Liu, Wang,Knochel, Paul
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p. 2200 - 2205
(2007/10/03)
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- FEXOFENADINE POLYMORPHS AND PROCESSES OF PREPARING THE SAME
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Anhydrous crystalline fexofenadine hydrochloride Form C, crystalline fexofenadine acetate monohydrate Form D, crystalline fexofenadine acetate dihydrate Form E and crystalline fexofenadine free base monohydrate Form F, processes of preparing the same, pharmaceutical compositions thereof, therapeutic uses thereof and methods of treatment therewith.
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Page/Page column 23
(2008/06/13)
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- PROCESS FOR PRODUCING DIHYDROISOQUINOLINE ZWITTERIONS
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This invention relates to a preparation of zwitterionic sulfates of substituted or unsubstituted 3, 4-dihydroisoquinoline.
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Page/Page column 15
(2008/06/13)
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- Method to inhibit ethylene responses in plants
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The present invention generally relates to methods of inhibiting ethylene responses in plants and plant materials, and particularly relates to methods of inhibiting various ethylene responses including plant maturation and degradation, by exposing plants to cyclopropene derivatives and compositions thereof wherein: 1) at least one substituent on the cyclopropene ring contains a carbocyclic or heterocyclic ring, or 2) . a substituent contains silicon, sulfur, phosphorous, or boron, or 3) least one substituent contains from one to four non-hydrogen atoms and at least one substituent contains more than four non-hydrogen atoms.
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Page/Page column 9
(2010/02/11)
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- Process for the synthesis of intermediates useful for the synthesis of tubulin inhibitors
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The invention is a process for the preparation of compounds of the Formula I: where R1, R2, R3, R4 and R5 are defined in the specification, which are intermediates useful for the preparation of tubulin inhibitors which are useful in the treatment of cancer.
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- A convenient ring formation of 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans from phenols and 2-aryl-2,2-dialkylacetaldehydes
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A new and simple route for the preparation of 3-aryl-2,2-dialkyl-2,3- dihydrobenzofurans from phenols is described. In the presence of an acid catalyst phenols react with 2-aryl-2,2-dialkylacetaldehydes, prepared in good yield from 2-arylacetonitriles in 2 steps, to give 3-aryl-2,2-dialkyl-2,3- dihydrobenzofurans. Electron-donating substituents were required on the phenols in order to give 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans in good yield.
- Yamashita, Makoto,Ono, Yujirou,Tawada, Hiroyuki
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p. 2843 - 2849
(2007/10/03)
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- A General Method for the Direct α-Arylation of Nitriles with Aryl Chlorides
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The long-standing challenge of developing a general method for the title methodology is met for a broad range of aryl chlorides through the use of bicyclic P(iBuNCH2CH2)3N (1) as a bulky electron-rich ligand for palladium (see scheme, dba = dibenzylideneacetone).
- You, Jingsong,Verkade, John G.
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p. 5051 - 5053
(2007/10/03)
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- P(i-BuNCH2CH2)3N: An efficient ligand for the direct α-arylation of nitriles with aryl bromides
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A new catalyst system for the synthesis of α-aryl-substituted nitriles is reported. The bicyclic triaminophosphine P(i-BuNCH 2CH2)3N (1b) serves as an efficient and versatile ligand for the palladium-catalyzed direct α-arylation of nitriles with aryl bromides. Using ligand 1b, ethyl cyanoacetate and primary as well as secondary nitriles are efficiently coupled with a wide variety of aryl bromides possessing electron-rich, electron-poor, electron-neutral, and sterically hindered groups.
- You, Jingsong,Verkade, John G.
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p. 8003 - 8007
(2007/10/03)
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- Intermediates useful for the preparation of antihistaminic piperidine derivatives
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The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula whereinW represents —C(=O)— or —CH(OH)—;R1 represents hydrogen or hydroxy;R2 represents hydrogen;R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2;n is an integer of from 1 to 5;m is an integer 0 or 1;R3 is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched each of A is hydrogen or hydroxy; andpharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1 and R2 are taken together to form a second bond between the carbon atoms bearing R1 and R2 or where R1 represented hydroxy, m is an integer 0.
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Page column 41-42
(2008/06/13)
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- Isoquinoline derivatives
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Compounds of formula (I) wherein: R1represents a substituent selected from: a hydrogen or halogen atom; a hydroxy, cyano, nitro, trifluoromethyl, trifluoromethoxy, trifluoromethanesulfonyloxy, pentafluoroethyl, C1-4alkyl, C1-4alkoxy, arylC1-4alkoxy, C1-4alkylthio, C1-4alkoxyC1-4alkyl, C3-6cycloalkylC1-4alkoxy, C1-4alkanoyl, C1-4alkoxycarbonyl, C1-4alkylsulfonyl, C1-4alkylsulfonyloxy, C1-4alkylsulfonylC1-4alkyl, arylsulfonyl, arylsulfonyloxy, arylsulfonylC1-4alkyl, C1-4alkylsulfonamido, C1-4alkylamido, C1-4alkylsulfonamidoC1-4alkyl, C1-4alkylamidoC1-4alkyl, arylsulfonamido, arylcarboxamido, arylsulfonamidoC1-4alkyl, arylcarboxamidoC1-4alkyl, aroyl, aroylC1-4alkyl, or arylC1-4alkanoyl group; a group R5OCO(CH2)p, R5(CON(R6)(CH2)p, R5R6NCO(CH2)p or R5R6NSO2(CH2)p where each of R5and R6independently represents a hydrogen atom or a C1-4alkyl group or R5R6forms part of a C3-6azacycloalkane or C3-6(2-oxo)azacycloalkane ring and p represents zero or an integer from 1 to 4; or a group Ar3—Z, wherein Ar3represents an optionally substituted phenyl ring or an optionally substituted 5- or 6-membered aromatic heterocyclic ring and Z representsa bond, O, S, or Ch2; R2 represents a hydrogen atom or a C1-4alkyl group; R3 and R4 each independently represent a C1-4alkyl group, q is 1 or 2; A represents a group of the formula (a), (b), (c), or (d).
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- Delivery systems for cyclopropenes
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The present invention relates to new delivery systems for cyclopropenes in which the cyclopropene, either free or encapsulated within a molecular encapsulation agent is incorporated into produce packaging materials.
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- Delivery systems for cyclopropenes
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The present invention relates to new delivery systems for cyclopropenes in which the cyclopropene, either free or encapsulated within a molecular encapsulation agent is incorporated into produce packaging materials.
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- Intermediates useful for the preparation of antihistaminic piperidine derivatives
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The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula wherein W represents —C(═O)— or —CH(OH)—; R1represents hydrogen or hydroxy; R2represents hydrogen; R1and R2taken together form a second bond between the carbon atoms bearing R1and R2; n is an integer of from 1 to 5; m is an integer 0 or 1; R3is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; each of A is hydrogen or hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1and R2are taken together to form a second bond between the carbon atoms bearing R1and R2or where R1represented hydroxy, m is an integer 0.
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