- Facile synthesis of size-tunable micro-octahedra via metal-organic coordination
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Single-crystalline micro-octahedra of Zn(PyrPy)2 with tunable sizes have been synthesized by manipulating the reaction kinetics of metal-organic coordination. The Royal Society of Chemistry 2009.
- Wang, Hao,Zeng, Yi,Ma, Jin Shi,Fu, Hongbing,Yao, Jiannian,Mikhaleva, Albina I.,Trofimov, Boris A.
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- Monoanionic Dipyrrin-Pyridine Ligands: Synthesis, Structure and Photophysical Properties
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A novel monoanionic tetradentate N4 ligand (F5DPPy) based on a dipyrromethene skeleton as a molecular platform and decorated with pyridine rings at the 1- and 9-positions of the dipyrrin motif has been prepared and characterized. Interestingly, although this ligand is weakly fluorescent, it presents a chelation-enhanced fluorescence effect of around 150 times upon coordination to ZnII. Time-dependent (TD) DFT calculations reproduce nicely the spectroscopic features of both the ligand and the complex, and analysis of the electron density redistribution in the excited state suggests that a better orbital overlap of the HOMO and LUMO in F5DPPyZnCl compared with F5DPPy is responsible for the more intense transitions observed with the former system. As such, this ligand opens interesting perspectives in the design of ratiometric sensors.
- Ducloiset, Clmence,Jouin, Pauline,Paredes, Elisa,Guillot, Rgis,Sircoglou, Marie,Orio, Maylis,Leibl, Winfried,Aukauloo, Ally
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- Nonempirical calculations of NMR indirect spin-spin coupling constants. Part 15: Pyrrolylpyridines
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Conformational study of 2-(2-pyrrolyl)pyridine and 2,6-di(2-pyrrolyl) pyridine was performed on the basis of the experimental measurements and high-level ab initio calculations of the one-bond 13C-13C, 13C-1H an
- Rusakov, Yury Yu.,Krivdin, Leonid B.,Schmidt, Elena Yu.,Mikhaleva, Albina I.,Trofimov, Boris A.
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- Preparation of N-arylpiperazines and other N-aryl compounds from aryl bromides as scaffolds of bioactive compounds
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Aryl bromides are coupled with N-compounds to give the corresponding arylamines in the presence of a palladium catalyst, a suitable ligand, and a weak base. The catalysts perform well for a large number of different starting material combinations at 100-150 °C with drops of toluene or without solvent, and with low catalyst levels (0.12 mol % Pd). The low catalyst amount makes the process environment friendly.
- Romero,Harrak,Basset,Ginet,Constans,Pujol
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- Neutral Cyclometalated Ir(III) Complexes with Pyridylpyrrole Ligand for Photocatalytic Hydrogen Generation from Water
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To explore structure-activity relationships with respect to light-harvesting behavior, a family of neutral iridium complexes [Ir(ppy)2(LR)] 1-4 (where ppy = 2-phenylpyridine, and NN = 2-(1H-pyrrol-2-yl)pyridine and its functionalized derivatives) were designed and synthesized. The structural modifications in metal complexes are accomplished through the attributions of electron-donating CH3 in 2, OCH3 in 3, and electron-withdrawing CF3 in 4. The structural analysis displays that the pyridylpyrrole acts as one-negative charged bidentated ligand to chelate the iridium center. The electrochemical and photophysical properties of these complexes were systematically studied. The neutral 1-4 as well as the ionic structurally analogous [Ir(ppy)2(bpy)](PF6) (5) were utilized as PSs in photocatalytic hydrogen generation from water with [Co(bpy)3](PF6)2 as catalyst and triethanolamine (TEOA) as electron sacrificial agent in the presence of salt LiCl. Complex 1 maintains activity for more than 144 h under irradiation, and the total turnover number is up to 1768. The electrochemical properties and the quenching reaction indicate the H2 generation by neutral complexes 1-4 is involved exclusively in the oxidative quenching process.
- Zhou, Yi,He, Piao,Mo, Xiu-Fang,Liu, Chao,Gan, Zhi-Liang,Tong, Hai-Xia,Yi, Xiao-Yi
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- Five (1H-pyrrol-2-yl)pyridines
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The title (1H-pyrrol-2-yl)pyridines, C9H8N2, substituted at the ortho, meta, and para positions of the pyridine ring all have hydrogen-bonded arrangements with geometrically similar, nearly linear, N(pyrrole)-H...N(pyridine) hydrogen bonds of average length. The graph sets for the ortho, meta, and three para polymorphs are R22(10), C(6), C(7), C(7), and R44(28), respectively.
- Noland, Wayland E.,Britton, Doyle
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- Conformational equilibria and photoinduced tautomerization in 2-(2′-pyridyl)pyrrole
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Depending on the polarity and protic abilities of the solvent, 2-(2′-pyridyl)pyrrole can exist in either syn or anti rotameric forms. In nonpolar solvents, intramolecular excited state single proton transfer is observed, manifested by the appearance of low-energy tautomeric emission. The solvent-assisted excited state double proton transfer reaction is also detected. DFT calculations confirm low barriers for both single and double proton transfer processes in the lowest excited singlet state and show different character of the tautomerization in both cases: in the intramolecular reaction, mutual approach of two nitrogen atoms plays an important role.
- Kijak, Micha?,Zielińska, Anna,Chamchoumis, Charles,Herbich, Jerzy,Thummel, Randolph P.,Waluk, Jacek
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- Intercepting a transient non-hemic pyridine: N -oxide Fe(iii) species involved in OAT reactions
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In the context of bioinspired OAT catalysis, we developed a tetradentate dipyrrinpyridine ligand, a hybrid of hemic and non-hemic models. The catalytic activity of the iron(iii) derivative was investigated in the presence of iodosylbenzene. Unexpectedly, MS, EPR, M?ssbauer, UV-visible and FTIR spectroscopic signatures supported by DFT calculations provide convincing evidence for the involvement of a relevant FeIII-O-NPy active intermediate. This journal is
- Vo, Nhat Tam,Herrero, Christian,Guillot, Régis,Inceoglu, Tanya,Leibl, Winfried,Clémancey, Martin,Dubourdeaux, Patrick,Blondin, Geneviève,Aukauloo, Ally,Sircoglou, Marie
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p. 12836 - 12839
(2021/12/10)
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- Hydrogen-bonded cyclic dimers at large compression: The case of 1h-pyrrolo[3,2-h]quinoline and 2-(2′-pyridyl)pyrrole
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1H-pyrrolo[3,2-h]qinoline (PQ) and 2-(2′-pyridyl)pyrrole (PP) are important systems in the study of proton-transfer reactions. These molecules possess hydrogen bond donor (pyrrole) and acceptor (pyridine) groups, which leads to the formation of cyclic dimers in their crystals. Herein, we present a joint experimental (Raman scattering) and computational (DFT modelling) study on the high-pressure behaviour of PQ and PP molecular crystals. Our results indicate that compression up to 10 GPa (100 kbar) leads to considerable strengthening of the intermolecular hydrogen bond within the cyclic dimers. However, the intramolecular N–H···N interaction is either weakly affected by pressure, as witnessed in PQ, or weakened due to compression-induced distortions of the molecule, as was found for PP. Therefore, we propose that the compression of these systems should facilitate double proton transfer within the cyclic dimers of PQ and PP, while intramolecular transfer should either remain unaffected (for PQ) or weakened (for PP).
- Chumak, Taisiia,Kurzyd?owski, Dominik,Listkowski, Arkadiusz,Rogo?a, Jakub
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supporting information
(2021/07/10)
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- Cis-Divacant Octahedral Fe(II) in a Dimensionally Reduced Family of 2-(Pyridin-2-yl)pyrrolide Complexes
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Four-coordinate transition-metal complexes can adopt a diverse array of coordination geometries, with square planar and tetrahedral coordination being the most prevalent. Previously, we reported the synthesis of a trinuclear Fe(II) complex, Fe3TPM2, supported by a 3-fold-symmetric 2-pyridylpyrrolide ligand [i.e., tris(5-(pyridin-2-yl)-1H-pyrrol-2-yl)methane] that featured a rare cis-divacant octahedral (CDO) geometry at each Fe(II) center. Here, a series of truncated 2-pyridylpyrrolide ligands are described that support mono- and binuclear Fe(II) complexes that also exhibit CDO geometries. Metalation of the tetradentate ligand bis[5-(pyridin-2-yl)-1H-pyrrol-2-yl]methane (H2BPM) in tetrahydrofuran (THF) results in the binuclear complex Fe2(BPM)2(THF)2 in which both Fe(II) ions are octahedrally coordinated. The coordinated THF solvent ligands are labile: THF dissociation leads to Fe2(BPM)2, which features five-coordinate Fe(II) ions. The Fe-Fe distance in these binuclear complexes can be elongated by ligand methylation. Metalation of bis[5-(6-methylpyridin-2-yl)-1H-pyrrol-2-yl]methane (H2BPMMe) in THF leads to the formation of four-coordinate, CDO Fe(II) centers in Fe(BPMMe)2. Further ligand truncation affords bidentate ligands 2-(1H-pyrrol-2-yl)pyridine (PyrPyrrH) and 2-methyl-6-(1H-pyrrol-2-yl)pyridine (PyrMePyrrH). Metalation of these ligands in THF affords six-coordinate complexes Fe(PyrPyrr)2(THF)2 and Fe(PyrMePyrr)2(THF)2. Dissociation of labile solvent ligands provides access to four-coordinate Fe(II) complexes. Ligand disproportionation at Fe(PyrPyrr)2 results in the formation of Fe(PyrPyrr)3 and Fe(0). Ligand methylation suppresses this disproportionation and enables isolation of Fe(PyrMePyrr)2, which is rigorously CDO. Complete ligand truncation, by separating the 2-pyridylpyrrolide ligands into the constituent monodentate pyridyl and pyrrolide donors, affords Fe(Pyr)2(Pyrr)2 in which Fe(II) is tetrahedrally coordinated. Computational analysis indicates that the potential energy surface that dictates the coordination geometry in this family of four-coordinate complexes is fairly flat in the vicinity of CDO coordination. These synthetic studies provide the structural basis to explore the implications of CDO geometry on Fe-catalyzed reactions.
- Hyun, Sung-Min,Lindahl, Paul A.,Powers, David C.,Reid, Kaleb A.,Vali, Shaik Waseem
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supporting information
p. 15617 - 15626
(2021/10/20)
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- Kineticversusthermodynamic metalation enables synthesis of isostructural homo- And heterometallic trinuclear clusters
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Temperature-dependent metalation of the new hexadentate ligand (tris(5-(pyridin-2-yl)-1H-pyrrol-2-yl)methane; H3TPM) enables the selective synthesis of both mononuclear (i.e.Na(THF)4[Fe(TPM)], kinetic product) and trinuclear (i.e.Fe
- Beaty, Jeremy D.,Bhuvanesh, Nattamai,Burns, Corey P.,Das, Anuvab,Hyun, Sung-Min,Nippe, Michael,Powers, David C.,Sung, Siyoung,Upadhyay, Apoorva
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supporting information
p. 5893 - 5896
(2020/06/05)
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- Synthesis of Decahydrocyclobuta[cd]indene Skeletons: Rhodium(III)-Catalyzed Hydroarylation and Relay Thiophene-Promoted Intramolecular [2+2] Cycloaddition
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The preparation of decahydrocyclobuta[cd]indene skeleton was accomplished through rhodium(III)-catalyzed hydroarylation and relay thiophene-promoted intramolecular [2+2] cycloaddition. This tandem reaction exhibited broad substrate scope (24 examples) and good functional group compatibility. Control experiments revealed the important role of sulfur (S) heteroatom, thus a tentative mechanism with thiophene-promoted double Michael additions was proposed to explain this formal [2+2] cycloaddition. Moreover, the resulting polycyclic products displayed potent anti-cancer activities against breast cancer cell lines MDA-MB-468. (Figure presented.).
- Gao, Dingding,Wang, Feng,Liu, Xing-Yu,Feng, Kai-Rui,Zhao, Jia-Ying,Wang, Yu-Hui,Yang, Xiao-Di,Tian, Ping,Lin, Guo-Qiang
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p. 4384 - 4390
(2020/09/23)
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- Enantioselective Synthesis of N-Benzylic Heterocycles: A Nickel and Photoredox Dual Catalysis Approach
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Reported herein is a dual nickel- and photoredox-catalyzed modular approach for the preparation of enantioenriched N-benzylic heterocycles. α-Heterocyclic carboxylic acids, easily obtainable from common commercial material, are reported as suitable substrates for a decarboxylative strategy in conjunction with a chiral pyridine-oxazoline (PyOx) ligand, providing quick access to enantioenriched drug-like products. The presence of a directing group on the heterocyclic moiety is shown to be beneficial, affording improved stereoselectivity in a number of cases.
- Pezzetta, Cristofer,Bonifazi, Davide,Davidson, Robert W. M.
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p. 8957 - 8961
(2019/11/11)
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- GRP94 SELECTIVE INHIBITORS AND USES THEREOF
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The present technology provides compounds according to Formula I or Formula III as well as compositions including such compounds useful for the treatment of metastatic cancer and/or glaucoma.
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Paragraph 0113; 0114; 0121
(2018/05/24)
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- For the preparation of pyridine [...] and its derivatives (by machine translation)
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A process for preparing pyridine [...] and derivatives thereof, first of all by the compound 2 - acetyl pyridine with hydroxylamine hydrochloride, polar organic solvent under the conditions of reaction [...] intermediate product methyl 2 - pyridyl oxime, then not isolate this intermediate product methyl 2 - pyridyl oxime circumstances, the heating of the reactor mixture, adding alkali to the reaction mixture, and inject the acetylene gas, the acetylene gas and the intermediate product methyl 2 - pyridine [...] generates cyclization reaction, to obtain 2 - (2 '- pyridyl) pyrrole and N - vinyl - 2 - (2' - pyridyl) pyrrole. The present invention is under the normal pressure access C2 H2 , Equipment requirements on the pressure resistance, atom utilization ratio is 100%, the under normal pressure of the glass material instrument reaction apparatus, reaction conditions suitable for ordinary laboratory and plant operation, accord with the green synthetic production technology. By experimental verification, the invention is simple to synthesize, raw materials are easy, separation and purification easy, high yield. (by machine translation)
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Paragraph 0038; 0039; 0040; 0046-0053
(2018/03/13)
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- Transformation of the non-selective aminocyclohexanol-based Hsp90 inhibitor into a Grp94-seletive scaffold
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Glucose regulated protein 94 kDa, Grp94, is the endoplasmic reticulum (ER) localized isoform of heat shock protein 90 (Hsp90) that is responsible for the trafficking and maturation of toll-like receptors, immunoglobulins, and integrins. As a result, Grp94 has emerged as a therapeutic target to disrupt cellular communication, adhesion, and tumor proliferation, potentially with fewer side effects compared to pan-inhibitors of all Hsp90 isoforms. Although, the N-terminal ATP binding site is highly conserved among all four Hsp90 isoforms, recent cocrystal structures of Grp94 have revealed subtle differences between Grp94 and other Hsp90 isoforms that has been exploited for the development of Grp94-selective inhibitors. In the current study, a structure-based approach has been applied to a Grp94 nonselective compound, SNX 2112, which led to the development of 8j (ACO1), a Grp94-selective inhibitor that manifests -440 nM affinity and ≥200-fold selectivity against cytosolic Hsp90 isoforms.
- Mishra, Sanket J.,Ghosh, Suman,Stothert, Andrew R.,Dickey, Chad A.,Blagg, Brian S. J.
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p. 244 - 253
(2017/12/30)
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- Palladium-Catalyzed Regioselective Dehydrogenative C–H/C–H Cross-Coupling of Pyrroles and Pyridine N-Oxides
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The palladium-catalyzed cross-dehydrogenative coupling of N-alkylpyrroles and pyridine N-oxides gave the corresponding pyrrolylpyridine N-oxides. Cu(OAc)2·H2O as a co-catalyst with air as the terminal oxidant led to preferential coupling in the β-position, whereas AgOAc as the stoichiometric oxidant resulted in preferential coupling in the α-position. N-(Benzyloxymethyl)pyrrole derivatives were deprotected by hydrogenolysis followed by basic hydrolysis.
- Liu, Shanshan,Tzschucke, C. Christoph
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supporting information
p. 3509 - 3513
(2016/07/28)
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- Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane
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2- and 2,3-Substituted pyrroles are readily synthesized in a one-pot procedure from ketones, hydroxylamine hydrochloride, and 1,2-dichloroethane in the KOH/DMSO system (120 °C, 2-4 h), the yields of pyrroles ranging 11-85%. Aliphatic, cycloaliphatic, aromatic, and heteroaromatic ketones tolerate the reaction conditions.
- Trofimov, Boris A.,Mikhaleva, Al'Bina I.,Ivanov, Andrei V.,Shcherbakova, Viktoria S.,Ushakov, Igor A.
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p. 124 - 128
(2015/02/02)
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- General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand
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A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.
- Zou, Yinjun,Yue, Guizhou,Xu, Jianwei,Zhou, Jianrong
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supporting information
p. 5901 - 5905
(2015/03/30)
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- Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles
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A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90-120 °C, 5-13 h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole - phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole - phenylacetylene and 2-(2-thienyl)pyrrole - phenylacetylene, respectively).
- Dvorko, Marina Yu.,Schmidt, Elena Yu.,Glotova, Tatyana E.,Shabalin, Dmitrii A.,Ushakov, Igor A.,Kobychev, Vladimir B.,Petrushenko, Konstantin B.,Mikhaleva, Al'Bina I.,Trofimov, Boris A.
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body text
p. 1963 - 1971
(2012/03/22)
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- A versatile method for suzuki cross-coupling reactions of nitrogen heterocycles
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(Chemical Equation Presented) A wide-ranging study of Suzuki reactions which use nitrogen-containing heterocycles is described (see scheme; dba = dibenzylideneacetone, Cy = cyclohexyl). This method is highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH2-and OH-substituted substrates), and efficient even with unactivated aryl chlorides.
- Kudo, Noriaki,Perseghini, Mauro,Fu, Gregory C.
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p. 1282 - 1284
(2007/10/03)
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- The triphenyl phosphite-chlorine reagent in the synthesis of pyrroles from N-allylamides
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A novel application of (PhO)3P-Cl2 chemistry to the synthesis of 2-substituted and 2,3-disubstituted pyrroles from N-allyl-amides is illustrated. A mild procedure is used to generate the imino chloride intermediates, which are subseq
- Spaggiari, Alberto,Vaccari, Daniele,Davoli, Paolo,Prati, Fabio
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p. 995 - 998
(2007/10/03)
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- Convenient access to 2-arylpyrroles from 2-lithio-N,N- dibenzylcyclopropylamine and nitriles
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N,N-Dibenzylaminocyclopropyl ketimines formed as intermediates upon treatment of 2-lithiated N,N-dibenzylcyclopropylamines with nitriles, being donor-acceptor-substituted cyclopropanes, immediately underwent ring-enlarging rearrangement and 1,2-elimination of dibenzylamine to produce 2-substituted pyrroles in good yields (14 examples, 55-80%). Georg Thieme Verlag Stuttgart.
- Tanguy, Chloé,Bertus, Philippe,Szymoniak, Jan,Larionov, Oleg V.,De Meijere, Armin
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p. 2339 - 2341
(2007/10/03)
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- Accelerated arene ligand exchange in the (arene)Cr(CO)2L series
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Arene ligand exchange in the (η6-arene)Cr(CO)2L series can be accelerated if the ligand L is an electronically unsymmetrical bidentate ligand. The system evaluated here employs derivatives of tris(pyrrolyl)-phosphine as L. A series of 2-L′-substituted pyrroles was prepared, where the substituents include: L′= -SMe, -CH2SMe, -SPh, -CH2SPh, -SCF3, -S-tBu, -CO2Me, -CONMe2, -2-pyridinyl, and -PPh2. Reaction with CIP(pyrrolyl)2 gave a new series of phosphines, (2-L′-pyrrolyl) (pyrrolyl)2P. Each of these phosphines was converted to (arene)Cr(CO)2[P(2-L′-pyrrolyl)(pyrrolyl)2P) complexes. The substituents L′ are proposed to provide temporary coordination to the Cr and to lower the barrier to arene exchange. The series was evaluated where the arene in the complex (departing) is benzene, fluorobenzene, toluene, o-oxylene, m-xylene, or p-xylene and the incoming arene is C6D6, chlorobenzene-d5, anisole-d 8, fluorobenzene-d5, toluene-d8, o-oxylene-d10, m-xylene-d10, p-xylene-d10, or mesitylene-d12. Most of the new complexes showed a significant increase in the rate of arene exchange due to the side chain unit L′. The strongest effects were seen with the examples where X = -CO2Me, -CONMe2, and -(2-pyridinyl), allowing exchange with a half lifetime as low as 8 h/22 °C.
- Semmelhack,Chlenov, Anatoly,Ho, Douglas M.
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p. 7759 - 7773
(2007/10/03)
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- 1H and 13C NMR study of the steric and electronic structure of 2-(pyridyl)pyrroles
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- 2-(Pyridyl)pyrroles are characterized by a strong π,π-conjugation between the pyridine and pyrrole rings, the latter being a π-donor. The electronic effect of trifluoroacetyl group is well transmitted thorugh the pyrrole fragment to the pyridine ring. 2-(3-Pyridyl)pyrrole was found to exist as two conformers with syn and anti arrangement of the heterorings; 2-(2-pyridyl)pyrrole exists mainly as the syn conformer stabilized by the weak intramolecular hydrogen bond N-H...N. The COCF3 group in position 2 of the pyrrole ring is oriented syn relative to the pyrrole fragment and is fixed by the intramolecular hydrogen bond N-H...O.
- Afonin,Ushakov,Petrova,Sobenina,Mikhaleva,Voronov,Trofimov
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p. 1043 - 1049
(2007/10/03)
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- Synthesis of 2-(2-Pyridyl)pyrrole and 2-(2-Pyridyl)-1-vinylpyrrole by the Trofimov Reaction
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2-(2-Pyridyl)pyrrole and 2-(2-pyridyl)-1-vinyl pyrroles were synthesized in 32 and 36% yield, respectively, by one-pot procedure from methyl 2-pyridyl ketone oxime and acetylene under a pressure of 16-25 atm in the system KOH-DMSO (105-110°C, 3 h), thus demonstrating for the first time the applicability of the Trofimov reaction to preparation of nicotine alkaloids.
- Petrova,Mikhaleva,Sobenina,Shmidt,Kositsina
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p. 1007 - 1009
(2007/10/03)
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- Silylamines in Organic Synthesis. Facile Synthetic Routes to Unsaturated Protected Primary Amines.
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The reactions of lithium N,N-bis(trimethylsilyl)aminomethyl acetylide with electrophilic reagents offered a short preparation of substituted and functional propargyl amines.These are shown to be useful precursors of various saturated protected primary amines.Addition reactions to the carbon-carbon triple bond or isomerisation reactions gave rise to allylic, dienic and α-allenic amines. Keywords: Silylamines; propargylamines, α-allenylamines; N,N-bis(silyl)dienamines.
- Corriu, Robert J. P.,Huynh, Vilam,Iqbal, Javed,Moreau, Joel J. E.,Vernhet, Claude
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p. 6231 - 6244
(2007/10/02)
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- PHOTO-ARYLATION III : SYNTHESIS OF 2-HETEROARYLPYRIDINES
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The title compounds were prepared in satisfactory yields by photo-reaction of 2-halopyridine (halogen; I,Br) with five membered heteroaromatics.
- Seki, Koh-ichi,Ohkura, Kazue,Terashima, Masanao,Kanaoka, Yuichi
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p. 2347 - 2350
(2007/10/02)
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