- Synthesis and deprotonation of 2-(pyridyl)phenols and 2-(pyridyl)anilines
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2-(2- and 3-Pyridyl)anilines (1, 2), 2,2-dimethyl-N-[2-(2- and 3-pyridyl)phenyl]propanamides (3, 4), and 2-, 3- and 4-(2-methoxyphenyl)pyridines (7-9) are readily synthesized using cross-coupling reactions. Whereas the amines 1, 2 undergo side reactions, the corresponding amides 3, 4 are deprotonated with lithium 2,2,6,6-tetramethylpiperidide (LTMP): the compound 3 at C6′ under in situ quenching, and the compound 4 at C4′. When the ether 7 is subjected to the same reagent, lithiation occurs at C6′.
- Rebstock, Anne-Sophie,Mongin, Florence,Trecourt, Francois,Queguiner, Guy
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- Pd-Catalyzed Remote Meta-C-H Functionalization of Phenylacetic Acids Using a Pyridine Template
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An effective pyridine based U-shaped template has been developed to enable a diverse range of meta-C-H functionalizations of phenylacetic acid scaffolds. This new template has extended the reaction scope to cross-coupling with ArBF3K as well as iodination using 1,3-diiodo-5,5-dimethylhydantoin as the iodination reagent.
- Jin, Zhong,Chu, Ling,Chen, Yan-Qiao,Yu, Jin-Quan
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- Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2
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An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.
- Gao, Yuzhen,Cai, Zhihua,Li, Shangda,Li, Gang
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supporting information
p. 3663 - 3669
(2019/05/17)
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- Visible-light-induced regioselective synthesis of polyheteroaromatic compounds
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A method for visible-light-induced synthesis of polyheteroaromatics from 2-heteroaryl-substituted anilines and heteroarylalkynes was developed. The process, which uses fac-Ir(ppy)3 as the photocatalyst and tBuONO as the diazotization reagent, is highly regioselective.
- Chatterjee, Tanmay,Choi, Myung Gil,Kim, Jun,Chang, Suk-Kyu,Cho, Eun Jin
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supporting information
p. 4203 - 4206
(2016/03/19)
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- N-Sulfonyl-aminobiaryls as Antitubulin Agents and Inhibitors of Signal Transducers and Activators of Transcription 3 (STAT3) Signaling
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A series of N-sulfonyl-aminobiaryl derivatives have been examined as novel antitubulin agents. Compound 21 [N-(4′-cyano-3′-fluoro-biphenyl-2-yl)-4-methoxy-benzenesulfonamide] exhibits remarkable antiproliferative activity against four cancer cell lines (pancreatic AsPC-1, lung A549, liver Hep3B, and prostate PC-3) with a mean GI50 value of 57.5 nM. Additional assays reveal that 21 inhibits not only tubulin polymerization but also the phosphorylation of STAT3 inhibition with an IC50 value of 0.2 μM. Four additional compounds (8, 10, 19, and 35) are also able to inhibit this phosphorylation. This study describes novel N-sulfonyl-aminobiaryl (biaryl-benzenesulfonamides) as potent anticancer agents targeting both STAT3 and tubulin. (Chemical Equation Presented).
- Lai, Mei-Jung,Lee, Hsueh-Yun,Chuang, Hsun-Yueh,Chang, Li-Hsun,Tsai, An-Chi,Chen, Mei-Chuan,Huang, Han-Lin,Wu, Yi-Wen,Teng, Che-Ming,Pan, Shiow-Lin,Liu, Yi-Min,Mehndiratta, Samir,Liou, Jing-Ping
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p. 6549 - 6558
(2015/09/07)
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- Efficient 11C-carbonylation of isolated aryl palladium complexes for PET: Application to challenging radiopharmaceutical synthesis
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We describe the successful implementation of palladium-aryl oxidative addition complexes as stoichiometric reagents in carbonylation reactions with 11CO to produce structurally challenging, pharmaceutically relevant compounds. This method enables the first 11C-carbonyl labeling of an approved PET tracer, [11C]raclopride, for the dopamine D2/D3 receptor by carbonylation with excellent radiochemical purity and yield. Two other molecules, [11C]olaparib and [11C]JNJ 31020028, were efficiently labeled in this manner. The technique distinguishes itself from existing methods by the markedly improved purity profiles of the tracer molecules produced and provides access to complex structures in synthetically useful yields, hereby offering a viable alternative to other 11C-labeling strategies.
- Andersen, Thomas L.,Friis, Stig D.,Audrain, Hlne,Nordeman, Patrik,Antoni, Gunnar,Skrydstrup, Troels
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supporting information
p. 1548 - 1555
(2015/03/05)
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- Synthesis and evaluation of imidazole-4,5-and pyrazine-2,3-dicarboxamides targeting dengue and yellow fever virus
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The results of a high-throughput screening assay using the dengue virus-2 replicon showed that the imidazole 4,5-dicarboxamide (I45DC) derivative (15a) has a high dengue virus inhibitory activity. Based on 15a as a lead compound, a novel class of both disubstituted I45DCs and the resembling pyrazine 2,3-dicarboxamides (P23DCs) were synthesized. Here, we report on their in vitro inhibitory activity against dengue virus (DENV) and yellow fever virus (YFV). Some of these first generation compounds have shown activity against both viruses in the micromolar range. Within this series, compound 15b was observed to display the highest antiviral potency against YFV with an EC50 Combining double low line 1.85 μM. In addition, compounds 20a and 20b both potently inhibited replication of DENV (EC50 Combining double low line 0.93 μM) in Vero cells.
- Saudi, Milind,Zmurko, Joanna,Kaptein, Suzanne,Rozenski, Jef,Neyts, Johan,Van Aerschot, Arthur
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p. 529 - 539
(2015/01/09)
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- Facile synthesis of 3-arylpyridine derivatives by palladacycle-catalyzed Stille cross-coupling reaction
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The Stille cross-coupling reaction of a variety of aryl halides (X=Cl, Br, I) with 3-alkylstannylpyridines highly catalyzed by cyclopalladated ferrocenylimine has been developed. This reaction allows formation of arylpyridine derivatives in moderate to excellent yields. Functional groups on aryl halides, such as amino, hydroxyl, keto, and aldehyde are tolerated and the reactions with arylbenzoxale substrates also proceed well.
- Ma, Gaizhi,Leng, Yuting,Wu, Yusheng,Wu, Yangjie
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p. 902 - 909
(2013/07/25)
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- O-(Trialkylstannyl)anilines and their utility in Migita-Kosugi-Stille cross-coupling: Direct introduction of the 2-aminophenyl substituent
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We have developed shelf- and air-stable ortho-stannylated aniline reagents that can directly be coupled with alkenyl and aryl halides via Migita-Kosugi-Stille cross-coupling. We report (i) the efficient preparation of o-(tributylstannyl)aniline (2a) and o-(trimethylstannyl)aniline (2b), (ii) the comparison of the reactivities of 2a and 2b with those of related organostannanes in cross-coupling reaction with an alkenyl halide, and (iii) the cross-coupling of 2a and 2b with a series of arylhalides and triflate.
- Izgu, Enver Cagri,Hoye, Thomas R.
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p. 4938 - 4941
(2012/11/07)
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- RhII2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides
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Approaching all isomers: A range of α-, β- and δ-carbolinium ions are readily available from ortho-substituted aryl azides using a rhodium(II) carboxylate catalyst (see scheme). The carbolinium ions are readily reduced to afford tryptolines or deprotonated to access pyridoindoles. This [RhII2]-catalyzed C-H bond amination was used in the synthesis of (±)-horsfiline and neocryptolepine. esp=α,α,α',α'- tetramethyl-1,3-benzenedipropionate. Copyright
- Pumphrey, Ashley L.,Dong, Huijun,Driver, Tom G.
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supporting information; experimental part
p. 5920 - 5923
(2012/08/07)
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- Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; Synthesis of dimebolin
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A range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize dimebolin in a concise and efficient manner.
- Dong, Huijun,Latka, Regina T.,Driver, Tom G.
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supporting information; experimental part
p. 2726 - 2729
(2011/06/28)
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- 2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction
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A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.
- Kim, Seung-Hoi,Rieke, Reuben D.
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scheme or table
p. 3135 - 3146
(2010/06/13)
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- Synthesis of nitrogen heterocycles by the ring opening of pyridinium salts
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(Chemical Equation Presented) The century-old ring-opening reaction of pyridinium salts with tethered nucleophiles has been harnessed for a synthesis of substituted indoles and related nitrogen heterocyles. Extension of this method could lead to oxygen- and sulfur-containing heterocycles and carbocycles, as well as to applications in natural product synthesis and medicinal chemistry.
- Kearney, Aaron M.,Vanderwal, Christopher D.
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p. 7803 - 7806
(2007/10/03)
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- Radical dearomatization of arenes and heteroarenes
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The stannane-mediated benzeneselenol-catalyzed addition of aryl iodides to a range of arenes and aromatic hetereocycles has been studied. With furan, thiophene, and several carbocyclic arenes, the addition takes place with quenching of the adduct radical by the catalytic selenol leading to moderate yields of aryl-dihydroarenes. With nitrogen heterocycles, on the other hand, it was not possible to suppress aromatization of the adduct radical and fully aromatized products were isolated. Aryl iodides bearing hydrogen bond donating groups in the ortho-position add to nitrogen heterocycles with high selectivity ortho- to the nitrogen, affording a simple one-step synthesis of potential chelating ligands. While 2-iodophenol is an excellent aryl radical source in these reactions, the homologous 1-iodo-2-naphthol fails owing to its reaction with diphenyl diselenide, which gives 1-phenylseleno-2-naphthol in high yield.
- Crich, David,Patel, Mitesh
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p. 7824 - 7837
(2007/10/03)
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- Direct synthesis of heterobiaryls by radical addition to pyridine: Expeditious synthesis of chelating ligands
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The addition of aryl radicals to pyridine may be affected in moderate yield on exposure of aryl iodides to tributyltin hydride, AIBN, and diphenyl diselenide in hot pyridine. Mixtures of ortho-, meta-, and para-aryl substituted pyridines are typically obtained. When the iodide is ortho-substituted with a hydrogen bond donor, such as o-iodophenol, significantly improved selectivity for ortho-substituted pyridines, with potential as bidentate chelating ligands, is obtained.
- Crich, David,Patel, Mitesh
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p. 499 - 504
(2007/10/03)
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- QUINOLINE DERIVATIVES
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The present invention relates to compounds of Formula I, wherein R1, R2, R3, R4, and n are as defined, and to pharmaceutically acceptable salts of said compounds. Compounds of Formula I have activity in agonizing 5HT7 receptors and are useful in treating, for example, disorders that can be treated by modulating circadian rhythms.
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