- Iridium-Catalyzed Cycloisomerization of Alkynoic Acids: Synthesis of Unsaturated Lactones
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The iridium-catalyzed cycloisomerization of various alkynoic acids was successfully developed, and a series of five-, six-, and especially seven-membered unsaturated lactones were constructed with moderate yields and excellent regioselectivities (up to 68
- Huang, Yi,Zhang, Xianghe,Dong, Xiu-Qin,Zhang, Xumu
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supporting information
p. 782 - 788
(2020/01/08)
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- INHIBITORS OF OPLOPHORUS LUCIFERASE-DERIVED BIOLUMINESCENT COMPLEXES
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Compounds that may selectively inhibit Oplophorus luciferase-derived bioluminescent complexes, e.g., NanoBiT? bioluminescent complex, are disclosed as well as compositions and kits comprising the compounds, and methods of using the compounds. The compounds are of formula (I) wherein R1-R4 and p and q are as defined in the claims.
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Paragraph 00175-00176; 00186; 00190-00191; 00250-00251
(2019/12/25)
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- Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts
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Alkynoic acids derived from salicylic acid and analogues undergo arylative cyclization with arenediazonium salts promoted by gold in the absence of external ligands. The reaction is thermally induced and proceeds even in the absence of light. A difference in regioselectivity has been found compared with that observed in the cycloisomerization process of the same type of compounds.
- Carrillo-Arcos, Ulises A.,Porcel, Susana
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p. 1837 - 1842
(2018/03/23)
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- Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
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A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).
- Zhao, Chun-Yang,Li, Kun,Pang, Yu,Li, Jia-Qing,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
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p. 1919 - 1925
(2018/03/28)
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- LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism
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Oxytocin (OT) and its receptor (OT-R) are implicated in the etiology of autism spectrum disorders (ASD), and OT-R is a potential target for therapeutic intervention. Very few nonpeptide oxytocin agonists have currently been reported. Their molecular and in vivo pharmacology remain to be clarified, and none of them has been shown to be efficient in improving social interaction in animal models relevant to ASD. In an attempt to rationalize the design of centrally active nonpeptide full agonists, we studied in a systematic way the structural determinants of the affinity and efficacy of representative ligands of the V1a and V2 vasopressin receptor subtypes (V1a-R and V2-R) and of the oxytocin receptor. Our results confirm the subtlety of the structure-affinity and structure-efficacy relationships around vasopressin/oxytocin receptor ligands and lead however to the first nonpeptide OT receptor agonist active in a mouse model of ASD after peripheral ip administration.
- Frantz, Marie-Céline,Pellissier, Lucie P.,Pflimlin, Elsa,Loison, Stéphanie,Gandiá, Jorge,Marsol, Claire,Durroux, Thierry,Mouillac, Bernard,Becker, Jér?me A. J.,Le Merrer, Julie,Valencia, Christel,Villa, Pascal,Bonnet, Dominique,Hibert, Marcel
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p. 8670 - 8692
(2018/10/05)
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- Visible Light Mediated Aryl Migration by Homolytic C?N Cleavage of Aryl Amines
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The photocatalytic preparation of aminoalkylated heteroarenes from haloalkylamides via a 1,4-aryl migration from nitrogen to carbon, conceptually analogous to a radical Smiles rearrangement, is reported. This method enables the substitution of amino group
- Alpers, Dirk,Cole, Kevin P.,Stephenson, Corey R. J.
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supporting information
p. 12167 - 12170
(2018/09/11)
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- Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O2: a facile protocol to selectively synthesize 2- and 3-vinylindoles
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A novel palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes using molecular oxygen as the terminal oxidant through β-carbon elimination of aminopalladation intermediates is disclosed. The reaction opens up an effective way to obtain a series of 2- and 3-vinylindoles which are important synthetic intermediates in many natural indole derivatives.
- Cao, Bo,Simaan, Marwan,Marek, Ilan,Wei, Yin,Shi, Min
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supporting information
p. 216 - 219
(2016/12/27)
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- Palladium-catalyzed cyclization of alkynoic acids to form vinyl dioxanones bearing a quaternary allylic carbon
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A palladium-catalyzed intramolecular reaction of carboxylic acids and alkynes in a novel cyclization manner was developed. This unique cyclization efficiently provided a wide range of complex ring systems-vinyl dioxanones bearing a quaternary allylic carbon. Mechanistic studies suggest an allenyl carboxylate as an intermediate.
- Ogiwara, Yohei,Sato, Kazuya,Sakai, Norio
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supporting information
p. 5296 - 5299
(2017/11/06)
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- BENZENE SULFONAMIDE-BASED INHIBITORS OF SPHINGOSINE KINASE
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A novel class of sphingosine kinase (SK) inhibitor compounds are disclosed which are useful in the treatment of cancer and other proliferative cell conditions. The compounds are benzene sulfonamides with a chemical structure according to formula (I).
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Paragraph 00137
(2016/03/13)
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- Iron-catalyzed N -arylsulfonamide formation through directly using nitroarenes as nitrogen sources
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One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.
- Zhang, Weixi,Xie, Junyao,Rao, Bin,Luo, Meiming
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p. 3504 - 3511
(2015/04/14)
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- Oxidative cyclization of alkenoic acids promoted by AgOAc
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Alkenoic acids derived from salicylic acid and analogues undergo an unexpected oxidative cyclization process triggered by AgOAc leading to 4H-benzo[d][1,3]dioxin-4-ones. The process is affected by the substitution on the aryl and the allyl units.
- Carrillo-Arcos, Ulises A.,Rojas-Ocampo, Jonathan,Porcel, Susana
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p. 479 - 483
(2016/01/09)
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- The effect of hydrogen bond on Br?nsted acid-catalyzed intramolecular hydroamination of unfunctionalized olefins
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The catalytic activity of benzoic acid could be increased by introducing a hydrogen bond donor group at the ortho-position. Preliminary DFT calculation indicated that the activation of CC double bond was realized by the action of both the carboxyl group and the hydrogen bond donor. The amino group was brought to the activated CC bond by the interaction between the carboxyl oxygen and amino proton. This interaction also increased the nucleophilicity of the amino group. Thus, in the presence of 20 mol % of 2-(trifluoromethanesulfonamido)benzoic acid, intramolecular hydroamination of unfunctionalized olefins gave the corresponding products in up to 95% isolated yields.
- Li, Ting-Ting,Liu, Gong-Qing,Wang, Yu-Mei,Cui, Bin,Sun, Hui,Li, Yue-Ming
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supporting information
p. 7003 - 7009
(2015/08/19)
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- Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions
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An iridium-catalyzed direct C-H amidation of weakly coordinating substrates, in particular of those bearing ester and ketone groups, under very mild conditions has been developed. The observed high reaction efficiency was achieved by the combined use of acetic acid and lithium carbonate as additives. Copyright
- Kim, Jinwoo,Chang, Sukbok
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p. 2203 - 2207
(2014/03/21)
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- Silver(I) and gold(I)-promoted synthesis of alkylidene lactones and 2H-chromenes from salicylic and anthranilic acid derivatives
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Ag(I) and Au(I) efficiently catalyze the cycloisomerization of terminal alkynoic acids into methylene seven-membered ring lactones. Depending on the metal, divergent reaction pathways were found for non terminal alkynoic acids. While Ag(I) led to lactones, Au(I) led to 2H-chromenes coming from the hydroarylation of the alkyne.
- Nolla-Saltiel, Roberto,Robles-Marín, Elvis,Porcel, Susana
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p. 4484 - 4488
(2014/08/05)
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- Theoretical studies, synthesis, and biological activity of 1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4- carbonitrile (C9) as a non-peptide antagonist of the arginine vasopressin V1a and V2 receptors
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In this work, the synthesis of 1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5- tetrahydro-1H-1-benzazepine-4-carbonitrile (C9) and the study of its biological activity as a new putative antagonist of vasopressin receptors are described. The chemical identific
- Contreras-Romo, M. Citlalli,Correa-Basurto, Jose,Padilla-Martinez, Itzia,Martinez-Archundia, Marlet,Martinez-Ramos, Federico,Slusarz, Magdalena J.,Lopez-Perez, Gilberto,Quintanar-Stephano, Andres
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p. 1581 - 1590
(2014/03/21)
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- The ant-pro reverse-turn motif. Structural features and conformational characteristics
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This article details the characteristic conformational features of the Ant-Pro reverse turn - a folded pseudo β-turn motif that displays a closed nine-membered-ring hydrogen-bonded network involving just two amino acid residues, namely anthranilic acid (A
- Thorat, Vijaykumar H.,Ingole, Tukaram S.,Vijayadas, Kuruppanthara N.,Nair, Roshna V.,Kale, Sangram S.,Ramesh, Veera V.E.,Davis, Hilda C.,Prabhakaran, Panchami,Gonnade, Rajesh G.,Gawade, Rupesh L.,Puranik, Vedavati G.,Rajamohanan, Pattuparambil R.,Sanjayan, Gangadhar J.
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p. 3529 - 3542
(2013/07/19)
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- Stereoselective synthesis of fluorinated 2,3-dihydroquinolin-4(1 H)-ones via a one-pot multistep transformation
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A new organocatalytic one-pot multistep transformation via Knoevenagel condensation/aza-Michael addition/electrophilic fluorination has been developed. Simple starting materials were used under mild conditions to construct fluorinated 2,3-dihydroquinolin-
- Li, Feng,Nie, Jing,Wu, Jun-Wei,Zheng, Yan,Ma, Jun-An
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experimental part
p. 2398 - 2406
(2012/05/20)
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- ANTI-RSV COMPOUNDS
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The present invention relates to anti-RSV compounds of Formula (I) and methods for use of the compounds in the treatment and prevention of RSV infection.
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Page/Page column 45
(2011/02/24)
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- Asymmetric synthesis of 2-Aryl-2,3-dihydro-4-quinolones via bifunctional thiourea-mediated intramolecular cyclization
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A novel asymmetric preparation of optically enriched 2-aryl-2,3- dihydroquinolin-4(1H)-ones has been developed. By installing a sulfonyl group on the nitrogen of the anilines and an ester function on the unsaturated ketones, an intramolecular organocataly
- Liu, Xiaoqian,Lu, Yixin
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supporting information; experimental part
p. 5592 - 5595
(2011/02/26)
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- VASOPRESSIN V1A ANTAGONISTS
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The present invention concerns compounds inter alia according to general formula 1a. Compounds according to the invention are vasopressin V 1a receptor antagonists. Pharmaceutical compositions of the compounds are useful as treatment of dysmenorrhoea.
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Page/Page column 32
(2008/06/13)
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- COMPOUNDS AND METHODS FOR TREATING DYSLIPIDEMIA
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Compounds of formula I wherein n, m, p, q, Y, R1 R2, R3, R4, R5, and R6 are as defined herein and their pharmaceutical compositions and methods of use are disclosed as useful for treating artherosclerosis and its sequelae.
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Page/Page column 37
(2008/06/13)
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- A new synthetic route to YM087, an arginine vasopressin antagonist
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A new synthesis of N-{4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl} biphenyl-2-carboxamide monohydrochloride (1, YM087) via new imidazobenzazepine intermediates is described. This method remarkably improves the overall yiel
- Tsunoda, Takashi,Tanaka, Akihiro,Mase, Toshiyasu,Sakamoto, Shuichi
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p. 1113 - 1122
(2007/10/03)
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- A formal synthesis of martinelline via a combination of two types of radical reactions
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A formal synthesis of martinelline has been accomplished via two types of radical reactions as the key steps. These are the radical addition-cyclization- elimination of an oxime ether carrying an unsaturated ester and a C-C bond formation through a radica
- Takeda, Yoshifumi,Nakabayashi, Toshiki,Shirai, Atsushi,Fukumoto, Daisuke,Kiguchi, Toshiko,Naito, Takeaki
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p. 3481 - 3484
(2007/10/03)
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- BENZAZEPINE DERIVATIVES, PROCESS FOR THE PREPARATION OF THE SAME AND USES THEREOF
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Compounds of the general formula (I): or salts thereof, which exhibit CCR5 antagonism and exert preventive and therapeutic effects against HIV infections: wherein R1 is a 5- to 6-membered aromatic ring which bears a substituent represented by the general formula: R-Z1-X-Z2- (wherein R1 is hydrogen or optionally substituted hydrocarbyl; X is optionally substituted alkylene; and Z1 and Z2 are each a heteroatom) and may be further substituted, with R being optionally bonded to the aromatic ring to form another ring; Y is optionally substituted imino; and R2 and R3 are each optionally substituted aliphatic hydrocarbyl or an optionally substituted hetero-alicyclic group.
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- Bismuth(III) chloride-catalyzed intramolecular hetero-Diels-Alder reactions: A novel synthesis of hexahydrodibenzo[b,h][1,6]naphthyridines
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BiCl3 efficiently catalyzed the intramolecular hetero-Diels-Alder reactions of aldimines generated in situ from aromatic amines and the N-allyl derivative of o-aminobenzaldehyde in refluxing acetonitrile to afford a novel class of hexahydrodibe
- Sabitha, Gowravaram,Venkata Reddy,Maruthi,Yadav
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p. 1573 - 1575
(2007/10/03)
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- Solid phase synthesis of sulfonamides using a carbamate linker
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A method for the synthesis of sulfonamides on a solid support by immobilizing amines through the nitrogen atom using a carbamate linkage is described.
- Raju,Kogan, Timothy P.
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p. 3373 - 3376
(2007/10/03)
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- Use of halomethyl resins to immobilize amines: An efficient method for synthesis of sulfonamides and amides on a solid support
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Methods for the synthesis of chloromethyl and bromomethyl equivalents of Wang's resin are described. To explore the utility of this acid clearable resin, amines were immobilized through the nitrogen atom, further functionalized, and then cleaved under acid conditions.
- Raju,Kogan, Timothy P.
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p. 4965 - 4968
(2007/10/03)
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- Acid-catalysed Cyclisation of o-Sulphonamido Ketene Dithioacetal S-Oxides: A Novel Synthesis of the Indole Ring System
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Treatment of o-sulphonamido aryl ketene dithioacetal S-oxides with hydrochloric acid in the presence of hydrogen sulphide gives 2-methylthioindoles.
- Hewson, Alan T.,Hughes, Kevin,Richardson, Steward K.,Sharpe, David A.,Wadsworth, Alan H.
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p. 1565 - 1569
(2007/10/02)
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