- Homogeneous and Gas–Liquid Catellani-Type Reaction Enabled by Continuous-Flow Chemistry
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A practical homogeneous and gas-liquid palladium-catalyzed Catellani-type reaction using a continuous-flow platform is described. The implementation of continuous-flow technology allowed the acceleration of the transformation and, for the first time, expansion of the chemical space to gaseous olefins (i.e., ethylene, propylene and 3,3,3-trifluoropropene), thus providing a safe and practical approach to sterically hindered ortho-disubstituted styrenes and vinyl arenes. The complete control over the stoichiometry of gaseous reagents through flow technology proved essential for directing the selectivity of the Catellani reaction to the desired products.
- Casnati, Alessandra,Gemoets, Hannes P. L.,Motti, Elena,Della Ca', Nicola,No?l, Timothy
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- Discovery of 5-{2-[5-Chloro-2-(5-ethoxyquinoline-8-sulfonamido)phenyl]ethynyl}-4-methoxypyridine-2-carboxylic Acid, a Highly Selective in Vivo Useable Chemical Probe to Dissect MCT4 Biology
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Due to increased lactate production during glucose metabolism, tumor cells heavily rely on efficient lactate transport to avoid intracellular lactate accumulation and acidification. Monocarboxylate transporter 4 (MCT4/SLC16A3) is a lactate transporter that plays a central role in tumor pH modulation. The discovery and optimization of a novel class of MCT4 inhibitors (hit 9a), identified by a cellular screening in MDA-MB-231, is described. Direct target interaction of the optimized compound 18n with the cytosolic domain of MCT4 was shown after solubilization of the GFP-tagged transporter by fluorescence cross-correlation spectroscopy and microscopic studies. In vitro treatment with 18n resulted in lactate efflux inhibition and reduction of cellular viability in MCT4 high expressing cells. Moreover, pharmacokinetic properties of 18n allowed assessment of lactate modulation and antitumor activity in a mouse tumor model. Thus, 18n represents a valuable tool for investigating selective MCT4 inhibition and its effect on tumor biology.
- Heinrich, Timo,Sala-Hojman, Ada,Ferretti, Roberta,Petersson, Carl,Minguzzi, Stefano,Gondela, Andrzej,Ramaswamy, Shivapriya,Bartosik, Anna,Czauderna, Frank,Crowley, Lindsey,Wahra, Pamela,Schilke, Heike,B?pple, Pia,Dudek, ?ukasz,Le?, Marcin,Niedziejko, Paulina,Olech, Kamila,Pawlik, Henryk,W?oszczak, ?ukasz,Zuchowicz, Karol,Suarez Alvarez, Jose Ramon,Martyka, Justyna,Sitek, Ewa,Mikulski, Maciej,Szcz??niak, Joanna,J?ckel, Sven,Krier, Mireille,Król, Marcin,Wegener, Ansgar,Ga??zowski, Micha?,Nowak, Mateusz,Becker, Frank,Herhaus, Christian
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p. 11904 - 11933
(2021/09/02)
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- SMALL MOLECULE INHIBITORS OF A PROTEIN COMPLEX
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Compositions and methods for treating thrombosis, inflammation, and atherosclerosis by administration of a compound that binds to KRIT1 to inhibit binding with HEG1.
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- Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes
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A mild, metal-free, atmospheric oxygen-mediated radical hydrothiolation of alkenes (and alkyne) is reported. A variety of sulfur containing motifs including alkanethiols, thiophenols and thioacids undergo an atmospheric oxygen-mediated radical hydrothiolation reaction with a plethora of alkenes in good yield with excellent functional group compatibility, typically with short reaction times to furnish a range of functionalized products. Biomolecules proved tolerant to the conditions and the procedure is robust and easily executable requiring no specialized equipment. Concise mechanistic studies confirm the process proceeds through radical intermediates in a thiol-ene reaction manifold. The methodology offers an efficient “green” approach for thiol-ene mediated “click” ligation and a milder alternative to thermally initiated hydrothiolation processes.
- McCourt, Ruairí O.,Scanlan, Eoin M.
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supporting information
p. 15804 - 15810
(2020/10/26)
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- Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons
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Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.
- Hemric, Brett N.,Chen, Andy W.,Wang, Qiu
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p. 1468 - 1488
(2019/01/25)
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- A Sequential Acyl Thiol-Ene and Thiolactonization Approach for the Synthesis of δ-Thiolactones
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A novel strategy for the synthesis of δ-thiolactones from inexpensive and readily available ?-unsaturated esters has been developed. This strategy incorporates a radical acyl thiol-ene reaction as the key C-S bond forming step. Cyclization is achieved via a Steglich-type thiolactonization of 5-mercaptopentanoic acids. We report the facile and scalable synthesis of δ-thiolactones in moderate to good yield under mild reaction conditions with tolerance for a range of functional groups.
- McCourt, Ruairí O.,Scanlan, Eoin M.
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supporting information
p. 3460 - 3464
(2019/05/10)
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- Iodine(III)-Mediated Electrochemical Trifluoroethoxylactonisation: Rational Reaction Optimisation and Prediction of Mediator Activity
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A new electrochemical iodine(III)-mediated cyclisation reaction for the synthesis of 4-(2,2,2-trifluoroethoxy)isochroman-1-ones is presented. Based on this reaction design of experiments and multivariate linear regression analysis were used to demonstrate
- M?ckel, Robert,Babaoglu, Emre,Hilt, Gerhard
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supporting information
p. 15781 - 15785
(2018/10/09)
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- Pd-Catalyzed Vinylation of Aryl Halides with Inexpensive Organosilicon Reagents Under Mild Conditions
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Pd-catalyzed Hiyama vinylation reaction of non-activated aryl chlorides and bromides under mild conditions was developed. The use of efficient vinyl donors and electron-rich sterically hindered phosphine ligands was critical for the success of the reaction. The products of this transformation can be used for Am/Cm separation, an important challenge in nuclear fuel reprocessing. The substituent effect on Am/Cm separating selectivity was also achieved, which could contribute to the development of new chromatographic materials for the separation of Am and Cm.
- Yang, Chu-Ting,Han, Jun,Liu, Jun,Li, Yi,Zhang, Fan,Yu, Hai-Zhu,Hu, Sheng,Wang, Xiaolin
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supporting information
p. 10324 - 10328
(2018/07/31)
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- Revisiting the Quinoxalinedione Scaffold in the Construction of New Ligands for the Ionotropic Glutamate Receptors
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More than two decades ago, the quinoxalinedione scaffold was shown to act as an α-amino acid bioisoster. Following extensive structure-activity relationship (SAR) studies, the antagonists DNQX, CNQX, and NBQX in the ionotropic glutamate receptor field were identified. In this work, we revisit the quinoxalinedione scaffold and explore the incorporation of an acid functionality in the 6-position. The SAR studies disclose that by this strategy it was possible to tune in iGluR selectivity among the AMPA, NMDA, and KA receptors, and to some extent also obtain full receptor subtype selectivity. Highlights of the study of 44 new analogues are compound 2m being a high affinity ligand for native AMPA receptors (IC50= 0.48 μM), analogues 2e,f,h,k,v all displayed selectivity for native NMDA receptors, and compounds 2s,t,u are selective ligand for the GluK1 receptor. Most interestingly, compound 2w was shown to be a GluK3-preferring ligand with full selectivity over native AMPA, KA and NMDA receptors.
- Demmer, Charles S.,Rombach, David,Liu, Na,Nielsen, Birgitte,Pickering, Darryl S.,Bunch, Lennart
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p. 2477 - 2495
(2017/11/21)
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- Atmosphere- and Temperature-Controlled Regioselective Aminobromination of Olefins
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A complete switch of regioselectivity in the aminobromination of olefins is realized from delicate changes in the reaction temperature from 25 °C to 40 °C and the atmosphere from air to argon, under catalyst-free conditions. The resulting α-bromoamides ca
- Yu, Wesley Zongrong,Cheng, Yi An,Wong, Ming Wah,Yeung, Ying-Yeung
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supporting information
p. 234 - 239
(2017/02/05)
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- Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source
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The enantioselective synthesis of 4-fluoroisochromanones via chiral aryl iodide-catalyzed fluorolactonization is reported. This methodology uses HF-pyridine as a nucleophilic fluoride source with a peracid stoichiometric oxidant and provides access to lactones containing fluorine-bearing stereogenic centers in high enantio- and diastereoselectivity. The regioselectivity observed in these lactonization reactions is complementary to that obtained with established asymmetric electrophilic fluorination protocols.
- Woerly, Eric M.,Banik, Steven M.,Jacobsen, Eric N.
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supporting information
p. 13858 - 13861
(2016/11/06)
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- PIPERIDINE ISOXAZOLE AND ISOTHIAZOLE OREXIN RECEPTOR ANTAGONISTS
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The present invention is directed to piperidine isoxazole and isothiazole orexin compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the prevention or treatment of such diseases in which orexin receptors are involved.
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Page/Page column 54
(2016/05/19)
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- 6,5-BICYCLIC OCTAHYDROPYRROLOPYRIDINE OREXIN RECEPTOR ANTAGONISTS
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The present invention is directed to 6,5-bicyclic octahydropyrrolopyridine compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
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Page/Page column 41
(2016/07/05)
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- METHYL OXAZOLE OREXIN RECEPTOR ANTAGONISTS
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The present invention is directed to methyl oxazole compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
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Page/Page column 43
(2016/06/28)
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- ETHYLDIAMINE OREXIN RECEPTOR ANTAGONISTS
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The present invention is directed to ethyldiamne compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
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Page/Page column 42
(2016/07/05)
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- BRIDGED DIAZEPANE OREXIN RECEPTOR ANTAGONISTS
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The present invention is directed to bridged diazepane compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
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Page/Page column 40
(2016/06/14)
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- Selective electrocarboxylation of bromostyrene at silver cathode in DMF
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The electroreduction behavior of bromostyrenes 1 in DMF has been detected by cyclic voltammetry (CV) on GC and Ag electrodes. Under the atmospheric pressure of CO2, selective electrocarboxylation of 1 was carried out in an undivided cell at Ag
- Wang, Hui-Mei,Sui, Guo-Jiao,Wu, Di,Feng, Qiu,Wang, Huan,Lu, Jia-Xing
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p. 968 - 972
(2016/02/03)
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- Breaking and Making of Olefins Simultaneously Using Ozonolysis: Application to the Synthesis of Useful Building Blocks and Macrocyclic Core of Solomonamides
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(Figure Presented) A simple and practical one-pot, two-directional approach to access olefinic esters through simultaneous breaking and making of olefins using ozonolysis of alkenyl aryl selenides is disclosed. The scope of the method with a variety of examples is demonstrated, and the end products obtained here are useful building blocks. As a direct application of the present method, the macrocyclic core of potent anti-inflammatory natural cyclic peptides, solomonamides, is synthesized.
- Kashinath,Dhara, Santu,Reddy, D. Srinivasa
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supporting information
p. 2090 - 2093
(2015/05/13)
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- Cis-specific hydrofluorination of alkenylarenes under palladium catalysis through an ionic pathway
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This paper describes the hydrofluorination of alkenes through sequential H- and F+ addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed. See attached PdF: A series of benzylic fluorides was prepared by hydrofluorination which proceeds through a PdII/IV catalytic manifold. The method is mechanistically distinct from previously reported radical hydrofluorination, and is characterized by its clean regioselectivity and unique cis stereospecificity. The first example of enantioselective net HF addition onto 2-vinylnaphthalene is also disclosed.
- Emer, Enrico,Pfeifer, Lukas,Brown, John M.,Gouverneur, Veronique
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supporting information
p. 4181 - 4185
(2014/05/06)
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- Supramolecular control of selectivity in hydroformylation of vinyl arenes: Easy access to valuable β-aldehyde intermediates
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Go against the flow! A rationally designed regioselective hydroformylation catalyst, [Rh/L], in which noncovalent ligand-substrate interactions allow the unprecedented reversal of selectivity from the typical α-aldehyde to the otherwise unfavored product β-aldehyde, is reported. This catalytic system opens up novel and sustainable synthetic pathways to important intermediates for the fine-chemicals industry.
- Dydio, Pawel,Reek, Joost N. H.
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supporting information
p. 3878 - 3882
(2013/05/09)
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- Design, synthesis, and pharmacological evaluation of glutamate carboxypeptidase II (GCPII) inhibitors based on thioalkylbenzoic acid scaffolds
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A series of thiol-based glutamate carboxypeptidase II (GCPII) inhibitors have been synthesized with either a 3-(mercaptomethyl)benzoic acid or 2-(2-mercaptoethyl)benzoic acid scaffold. Potent inhibitors were identified from each of the two scaffolds with IC50 values in the single-digit nanomolar range, including 2-(3-carboxybenzyloxy)-5-(mercaptomethyl)benzoic acid 27c and 3-(2-mercaptoethyl)biphenyl-2,3'-dicarboxylicacid 35c. Compound 35c was found to be metabolically stable and selective over a number of targets related to glutamate-mediated neurotransmission. Furthermore, compound 35c was found to be orally available in rats and exhibited efficacy in an animal model of neuropathic pain following oral administration.
- Stoermer, Doris,Vitharana, Dilrukshi,Hin, Niyada,Delahanty, Greg,Duvall, Bridget,Ferraris, Dana V.,Grella, Brian S.,Hoover, Randall,Rojas, Camilo,Shanholtz, Megan K.,Smith, Kyle P.,Stathis, Marigo,Wu, Ying,Wozniak, Krystyna M.,Slusher, Barbara S.,Tsukamoto, Takashi
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experimental part
p. 5922 - 5932
(2012/07/30)
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- Enantiodifferentiating endo-selective oxylactonization of ortho-alk-l-enylbenzoate with a lactate-derived aryl-λ3-iodane
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It's the hype: The asymmetric synthesis of 3-alkyl-4-oxyisochroman-1-one is achieved by oxylactonization of ortho-alk-1-enylbenzoate with a series of optically active hypervalent iodine(III) reagents prepared from lactate or valine as a chiral source (see scheme). The oxylactonization is highly regio-, diastereo-, and enantioselective. 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
- Fujita, Morifumi,Yoshida, Yasushi,Miyata, Kazuyuki,Wakisaka, Akihiro,Sugimura, Takashi
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supporting information; experimental part
p. 7068 - 7071
(2010/11/18)
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- Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles
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The reaction of silyl-substituted carbanion 1b with arene-1,2-dicarboxylates 6, 15 yields indenone derivatives 11, 16 in a domino process involving silyl C→O migration and elimination. However, in a competing pathway, the initial addition of 1b leads to l
- Genrich, Florian,Harms, Guido,Schaumann, Ernst,Gjikaj, Mimoza,Adiwidjaja, Gunadi
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experimental part
p. 5577 - 5587
(2009/12/03)
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- Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes
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(NHC)-Cu (NHC = N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.
- Lebel, Helene,Davi, Michael,Diez-Gonzalez, Silvia,Nolan, Steven P.
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p. 144 - 149
(2007/10/03)
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- Pd-Catalyzed Cross-Coupling of Haloarenes and Chloroarene-Cr(CO) 3 Complexes with Stabilized Vinyl- and Allylaluminium Reagents
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The palladium-catalyzed cross-coupling of intramolecularly stabilized divinyl- and diallylaluminium compounds 1 and 2 with haloarenes and chloroarene-Cr(CO)3 complexes has been studied. The coupling products were obtained in high yields (up to
- Schumann, Herbert,Kaufmann, Jens,Schmalz, Hans-Günther,B?ttcher, Andreas,Gotov, Battsengel
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p. 1783 - 1788
(2007/10/03)
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- Cross-coupling of vinylpolysiloxanes with aryl iodides
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Commercially available vinylpolysiloxane (1) rapidly undergoes cross-coupling reactions with aryl and alkenyl iodides in the presence of tetrabutylammonium fluoride (two to three equivalents) and Pd(dba)2 (1-5 mol%) at room temperature to affor
- Denmark, Scott E.,Wang, Zhigang
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p. 372 - 375
(2007/10/03)
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- Exploiting poly(ethylene glycol) as a matrix for liquid-phase organic synthesis
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Soluble polymer-supported chemistry is a technology that allows the blending of the benefits of polymer-supported synthesis and solution-phase chemistry. Herein, we describe our recent efforts in this area targeted at exploring the scope of poly(ethylene glycol) (PEG) as the matrix. Specifically we describe the use of PEG as a support for triphenyl phosphine and for the Stille reaction.
- Sieber, Frank,Wentworth Jr., Paul,Janda, Kim D.
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p. 1018 - 1032
(2007/10/03)
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- 1-methyl-1-vinyl- and 1-methyl-1-(prop-2-enyl)silacyclobutane: Reagents for palladium-catalyzed cross-coupling reactions of aryl halides
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1-Methyl-1-vinylsilacyclobutane (1) and 1-methyl-1(prop-2- enyl)silacyclobutane (2) undergo rapid and high yielding cross-coupling with aromatic halides. Many different substituents and patterns on the aromatic moiety are tolerated. All reactions can be r
- Denmark, Scott E.,Wang, Zhigang
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p. 999 - 1003
(2007/10/03)
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- Palladium-catalyzed carbonylative cyclization of 1-iodo-2-alkenylbenzenes
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The Pd-catalyzed carbonylation of ω-vinyl-substituted o-iodoalkenylbenzenes 1-4 can provide up to modest yields (50-60%) of 5- and 6-membered Type I cyclic acylpalladation products, i.e., α,β-unsaturated cyclic ketones, in the absence of an external nucleophile and high yields of 5- and 6-membered Type II cyclic acylpalladation products, i.e., α- or β-((alkoxycarbonyl)methyl)substituted cyclic ketones in the presence of an alcohol, e.g., MeOH. In cases where no such processes are available, other side reactions, such as cyclic carbopalladation, polymeric acylpalladation, and trapping of acylpalladiums via esterification and other processes may become predominant. Neither smaller, i.e., 3- or 4-membered, nor 7-membered or larger cyclic ketones appear to be accessible by the reaction. In most cases, the exo-mode cyclic acylpalladation takes place exclusively. However, the cyclic acylpalladation of 3 proceeds exclusively via endo-mode cyclization to give 5-membered ketones. Substitution of one or more hydrogens in the ω-vinyl group with carbon groups has significant effects on the reaction course. Those substrates containing a 1,2-disubstituted alkenyl group in place of a vinyl group, i.e., 19-22 and 24 excluding 25, can give monomeric cyclic acylpalladation products in high yields. These results represent a major deviation from those obtained with 1 and 2. In the absence of an external nucleophile, formation of Type I cyclic acylpalladation products is, in some cases, accompanied by Type III cyclic acylpalladation involving trapping of acylpalladiums by internal enolates. In the presence of MeOH or other alcohols, Type II acylpalladation products have been obtained in respectable yields from 19-20, 23, and 24. In the presence of an alcohol, premature esterification can be a serious side reaction. However, this problem can be alleviated using i-PrOH or t-BuOH in place of MeOH in combination with appropriate solvents, typically those of lower polarity. Heteroatom-containing substituents on the ω-vinyl groups also exert significant effects on cyclic acylpalladation. Electron-donating substituents tend to lead to high yields of cyclic acylpalladation products, while electron-withdrawing alkoxycarbonyl groups conjugated with the ω-alkenyl group tend to give lower yields of cyclic acylpalladation products. With Me3Si and alkoxycarbonyl groups products of apparent endo-mode cyclic acylpalladation, i.e., naphthols, have been obtained in significant yields (25-50%). Free OH and other nucleophilic heteroatom groups can seriously interfere with cyclic acylpalladation, and they must be appropriately protected in most cases, although there are indications that acylpalladation-lactonization tandem processes similar to Type II cyclic acylpalladation might be developed.
- Negishi, Ei-Ichi,Copéret, Christophe,Ma, Shengming,Mita, Takeshi,Sugihara, Takumichi,Tour, James M.
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p. 5904 - 5918
(2007/10/03)
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- A comparative Study of the Decomposition of o-Alkynyl-Substituted Aryl Diazo Ketones. Synthesis of Polysubstituted β-Naphthols via Arylketene Intermediates
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The photochemical, thermal, and rhodium-catalyzed decomposition reactions of several closely related o-alkynyl or o-alkenyl α-diazoaceto- and propiophenone derivatives have been studied.The reaction outcome is markedly dependent upon the reaction conditions employed for nitrogen extrusion.Thermolysis or photolysis of o-alkynyl α-diazopropiophenone derivatives yields polysubstituted β-naphthols.These products are derived from Wolff rearrangement of the initially formed carbene to give an aryl ketene which undergoes intramolecular cyclization onto the o-alkynylsubstituent.In direct contrast to the thermal and photochemical results, Rh(II)-catalyzed decomposition yields products derived from direct attack of a rhodium carbenoid onto the tethered ?-system producing a vinyl carbenoid intermediate.Further reaction of the cyclized carbenoid with the starting diazo compound furnished a vinyl indenone which undergoes a rapid intramolecular Diels-Alder reaction to produce a novel dimer whose structure was elucidated by an X-ray crystal analysis.Replacement of the methyl group on the diazo center with a sterically less demanding hydrogen atom was also found to play an important role in controlling the outcome of the Rh(II)-catalyzed reaction.
- Padwa, Albert,Chiacchio, Ugo,Fairfax, David J.,Kassir, Jamal J.,Litrico, Angelo,at al.
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p. 6429 - 6437
(2007/10/02)
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- Synthesis of spirononane system present in fredericamycin A
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Two different approaches for the construction of spirononane system present in fredericamycin A (1) have been reported.In the first approach (2-(β-haloethyl)phenyl)-indane-1,3-dione-methyl enolate (17) was subjected to trimethylsilyliodide reaction
- Rao, A. V. Rama,Rao, B. Venkateswara,Reddy, D. Reddappa
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p. 723 - 727
(2007/10/02)
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- Palladium-catalyzed Synthesis of Isocoumarin and 1-Isoquinolinone Derivatives
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In the presence of copper(I) chloride, the palladium catalyzed oxidation of methyl 2-ethenylbenzoates and 2-ethenylbenzamides have been studied.This reaction was used to form isocoumarins and 1-isoquinolinones.
- Izumi, Taeko,Nishimoto, Yasuhiro,Kohei, Kunihiro,Kasahara, Akira
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p. 1419 - 1424
(2007/10/02)
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- Palladium(II)-mediated Synthesis of Spirononane System Present in Fredericamycin A
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A convenient approach for the construction of spirononane system present in fredericamycin A (1) has been achieved utilizing Pd(II) acetate mediated cyclisation of the 1,3-indanedione intermediate (10).
- Rao, A. V. Rama,Reddy, D. Reddeppa,Rao, B. Venkateswara
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p. 1065 - 1066
(2007/10/02)
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- Nitrile Oxide Cycloaddtion Routes to 2-(Isoxazolyl)benzoates and 2-(1,2,4-Oxadiazol-3-yl)benzoates
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Cycloaddition of aromatic nitrile oxides to methyl o-vinylbenzoate produced methyl 2-(3-aryl-2-isoxazolin-5-yl)benzoates; the isoxazolines were converted to methyl 2-(3-arylisoxazol-5-yl)benzoates.Reaction of the nitrile oxide from o-methoxycarbonylbenzohydroximinoyl chloride (11) with phenylacetylene, styrenes, and aromatic nitriles resulted in methyl 2-(5-phenylisoxazol-3-yl)benzoate, methyl 2-(5-aryl-2-isoxazolin-3-yl)benzoates (15) and methyl 2-(5-aryl-1,2,4-oxadiazol-3-yl)benzoates, respectively.The isoxazolines 15 were converted to the corresponding isoxazoles 16.
- Howe, Robert K.,Schleppnik, Frances M.
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p. 721 - 726
(2007/10/02)
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- Trifluoromethylphenyl isoxazolyl benzoates
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The invention relates to 3-trifluoromethylphenylisoxazol-5-yl-benzoates and their use as herbicides or plant growth regulants.
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- 2-[3-Aryl-2-isoxazolin-5-yl]benzoates
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2-[3-aryl-2-isoxazolin-5-yl]benzoates and their use as intermediates for agricultural chemicals. The subject isoxazolines can be converted to the corresponding isoxazoles. The latter are useful as herbicides and as plant growth regulants.
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