- Domino [Pd]-Catalysis: Heck followed by decarboxylative Sonogashira couplings under microwave irradiation in aqueous medium
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A copper free [Pd]-catalyzed domino intramolecular Heck and intermolecular decarboxylative Sonogashira couplings, for the synthesis of alkyne bearing heterocyclic compounds with a quaternary carbon atom, is described. Notably, this dual bond forming strategy is successful in water solvent, under microwave irradiation. This one-pot operation enabled the formation of a variety of dihydrobenzofurans, indolines and oxindoles, in very good to near quantitative yields. Notably, unlike earlier reports, the present strategy is successful in delivering the products with short alkyl substituents on acetylene carbon, which is first of its kind.
- Ramesh, Karu,Satyanarayana, Gedu
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Read Online
- Synthesis of All-Carbon Quaternary Centers by Palladium-Catalyzed Olefin Dicarbofunctionalization
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The redox-neutral dicarbofunctionalization of tri- and tetrasubstituted olefins to form a variety of (hetero)cyclic compounds under photoinduced palladium catalysis is described. This cascade reaction process was used to couple styrenes or acryl amides with a broad range of highly decorated olefins tethered to aryl or alkyl bromides (>50 examples). This procedure enables one or two contiguous all-carbon quaternary centers to be formed in a single step. The products could be readily diversified and applied in the synthesis of a bioactive oxindole analogue.
- Koy, Maximilian,Bellotti, Peter,Katzenburg, Felix,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 2375 - 2379
(2020/01/24)
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- HETEROCYCLIC COMPOUND
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Provided is a heterocyclic compound having a superior RBP4-lowering action and useful as a medicament for the prophylaxis or treatment of a disease or symptom mediated by an increase in RBP4 or retinol supplied by RBP4. A compound represented by the formula (I): wherein each symbol is as defined in the Description, or a salt thereof has a superior RBP4-lowering action, and is useful as a medicament for the prophylaxis or treatment of a disease or symptom mediated by an increase in RBP4 or retinol supplied by RBP4.
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- Palladium-catalyzed domino Mizoroki-Heck/intermolecular C(sp3)-H activation sequence: An approach to the formation of C(sp3)-C(sp3) bonds
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A palladium-catalyzed domino Mizoroki-Heck/intermolecular unactivated C(sp3)-H alkylation reaction has been developed. This simple palladium nanoparticle catalytic system shows good activity and affords the dimeric dihydrobenzofuran derivatives
- Wang, Wei,Zhou, Rong,Jiang, Zhi-Jie,Wang, Xin,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua,Li, Rui-Xiang
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supporting information
p. 2579 - 2584
(2015/04/27)
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- Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes
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A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.
- Gao, Yang,Xiong, Wenfang,Chen, Huoji,Wu, Wanqing,Peng, Jianwen,Gao, Yinglan,Jiang, Huanfeng
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p. 7456 - 7467
(2015/08/18)
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- DNA-PK INHIBITORS
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The present invention relates to compounds useful as inhibitors of DNA-PK. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders.
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Paragraph 0226
(2013/11/05)
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- Synthesis of new 4,5-dihydrofuranoindoles and their evaluation as HCV NS5B polymerase inhibitors
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The synthesis of substituted 3,4-dihydrofuranoindoles is reported. These new indole compounds were used to synthesize potent HCV NS5B inhibitors. The binding mode of the dihydrofuranoindole-derived inhibitors was established via X-ray crystallographic stu
- Velazquez, Francisco,Venkatraman, Srikanth,Lesburg, Charles A.,Duca, Jose,Rosenblum, Stuart B.,Kozlowski, Joseph A.,Njoroge, F. George
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supporting information; experimental part
p. 556 - 559
(2012/03/26)
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- HETEROCYCLIC ANTIVIRAL COMPOUNDS
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Compounds having the formula I wherein R1, R2, R3, R4, R5a, R5b, R5c and R6 are as defined herein are Hepatitis C virus NS5b polymerase inhibitors. Also disclosed are
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Page/Page column 47
(2010/11/05)
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- HETEROCYCLIC ANTIVIRAL COMPOUNDS
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Compounds having the formula I wherein wherein R1, R2, R3b, R4a, R4b, R4c and as defined herein are Hepatitis C virus NS5b polymerase inhibitors. Also disclosed are compositions and methods
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Page/Page column 29
(2010/12/29)
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- Pd-Catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine
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(Figure presented) The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority of benzlodoxolone-derlved hypervalent iodine reagent 3d as an alkyne transfer reagent further expands the rapidly increasing utility of hypervalent iodine reagents in catalysis and is expected to have important implications for other similar processes.
- Nicolal, Stefano,Erard, Stephane,Gonzalez, Davinla Fernandez,Waser, Jerome
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supporting information; experimental part
p. 384 - 387
(2010/03/04)
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- Domino palladium-catalyzed heck-intermolecular direct arylation reactions
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A domino palladium-catalyzed Heck-intermolecular direct arylation reaction has been developed, giving access to a variety of dihydrobenzofurans, indolines, and oxindoles. A variety of sulfur-containing heterocycles such as thiazoles, thiophenes, and benzo
- Rene, Olivier,Lapointe, David,Fagnou, Keith
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supporting information; experimental part
p. 4560 - 4563
(2009/12/05)
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- 4,5-RING ANNULATED INDOLE DERIVATIVES FOR TREATING OR PREVENTING OF HCV AND RELATED VIRAL INFECTIONS
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The present invention relates to 4,5-ring annulated indole derivatives, compositions comprising at least one 4,5-ring annulated indole derivatives, and methods of using the 4,5-ring annulated indole derivatives for treating or preventing a viral infection or a virus-related disorder in a patient. Wherein ring Z, of formula (I), is a cyclopentyl, cyclopentenyl, 5-membered heterocycloalkyl, 5-membered heterocycloalkenyl or 5-membered heteroaryl ring.
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Page/Page column 182-183
(2008/12/07)
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- Synthesis of heterocycles via ligand-free palladium catalyzed reductive Heck cyclization
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Synthesis of five and six membered heterocycles, indolines, 2,3-dihydrobenzofurans, chromans, isochromans, 1,2,3,4-tetrahydroquinolines, and 1,2,3,4-tetrahydroisoquinolines, in 70-99% yield by a ligand-free palladium catalyzed reductive Heck cyclization of phenyl bromides and chlorides, under mild conditions, is reported. Water was found to be essential for these reactions.
- Liu, Pingli,Huang, Liang,Lu, Yuelie,Dilmeghani, Mina,Baum, Jean,Xiang, Tingjian,Adams, Jeff,Tasker, Andrew,Larsen, Rob,Faul, Margaret M.
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p. 2307 - 2310
(2007/10/03)
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- On the Reactivity of o-Lithioaryl Ethers: Tandem Anion Translocation and Wittig Rearrangement
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(matrix presented) Allyl and benzyl 2-lithioaryl ethers, generated by bromine-lithium exchange in THF, undergo a new tandem anion translocation-[1,2]-Wittig rearrangement allowing the isolation of the corresponding benzylic alcohols.
- Barluenga, Jose,Fananas, Francisco J.,Sanz, Roberto,Marcos, Cesar,Trabada, Marta
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p. 1587 - 1590
(2007/10/03)
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- Selectivity in the tandem cyclization - Carboxylation reaction of unsaturated haloaryl ethers catalyzed by electrogenerated nickel complexes
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The electrochemical reduction of a series of 2-haloaryl ethers containing allyl and propargyl groups under CO2 allows the synthesis of benzofuranacetic acid derivatives. This novel intramolecular cyclization- carboxylation reaction is carried out in single-compartment cells and is catalyzed by [Ni(cyclam)Br2].
- Olivero,Du?ach
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p. 1885 - 1891
(2007/10/03)
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- New cyclooxygenase-2/5-lipoxygenase inhibitors. 2. 7-tert-butyl-2,3- dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: Variations of the dihydrobenzofuran ring
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A series of 5-keto-substituted 7-tert-butyl-2,3-dihydro-3,3- dimethylbenzofurans (DHDMBFs) were found to be nonsteroidal antiinflammatory and analgesic agents. These compounds are inhibitors of 5-1ipoxygenase (5- LOX) and cyclooxygenase (COX) with selectivity for the COX-2 isoform. A series of analogues were prepared to investigate the scope of this lead. Five ketone side chains from active DHDMBFs were used to investigate the effects of changes in the DHDMBF 'core': the size and identity of the heterocycle and the substituent requirements of the heterocycle and phenyl ring. Biological testing showed that a variety of structural changes can be accommodated, but no structure was clearly superior to the DHDMBF structure.
- Janusz, John M.,Young, Patricia A.,Scherz, Michael W.,Enzweiler, Kevin,Wu, Laurence I.,Gan, Lixian,Pikul, Stanislaw,McDow-Dunham, Kelly L.,Johnson, Carl R.,Senanayake,Kellstein, David E.,Green, Shelley A.,Tulich, Julie L.,Rosario-Jansen, Theresa,Jack Magrisso,Wehmeyer, Kenneth R.,Kuhlenbeck, Deborah L.,Eichhold, Thomas H.,Dobson, Roy L. M.
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p. 1124 - 1137
(2007/10/03)
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- 2,3-Dihydro-7-benzofurancarboxylic Acids
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The syntheses of a series of title compounds 1 a-f bearing methyl groups in the heterocyclic part were described.Depending on the substitution pattern the Claisen rearrangement (path A) or the methodology of directed lithiations (path B) were used as the
- Stanetty, Peter,Koller, Herbert,Puerstinger, Gerhard
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p. 883 - 891
(2007/10/02)
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