- Improved synthesis of 5,5"-dibromo-2,2′:6′,2"-terpyridine
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5,5"-dibromo-2,2′:6′,2"-terpyridine has been synthesized in very good yield and on a multigram scale modifying the Stille cross-coupling strategy published by Schlüter and coworkers in a previous work.
- Colasson, Beno?t X.,Dietrich-Buchecker, Christiane,Sauvage, Jean-Pierre
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Read Online
- Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide
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A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.
- Mukhopadhyay, Sushobhan,Batra, Sanjay
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supporting information
p. 14622 - 14626
(2018/09/21)
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- A New, Simple, and General Synthesis of N -Oxides of Iodopyridines and Iodoquinolines via the Diazotization-Iodination of Heterocyclic Amino N -Oxides in the Presence of p -Toluenesulfonic Acid in Water
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The diazotization of a series of N -oxides of aminopyridines and aminoquinolines under the action of sodium nitrite in the presence of KI and p -TsOH in water at room temperature leads to the formation of the corresponding N -oxides of iodopyridines and iodoquinolines in high yields. The method has a general character and can be used for the preparation of 3-, 2-, and 4- N -oxides of iodopyridines.
- Krasnokutskaya, Elena A.,Chudinov, Alexey A.,Filimonov, Victor D.
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p. 1368 - 1372
(2017/12/26)
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- ELECTROCHROMIC COMPOUNDS AND OPTICAL ARTICLES CONTAINING THEM
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The present invention relates to a group of novel electrochromic compounds. More specifically, it relates to electrochromic compounds comprising one or several pyridinium rings and the use of these compounds as a variable transmittance medium for the manufacture of an optical article, such as an ophthalmic lens.
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Page/Page column 20; 21
(2018/07/31)
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- Hybrid charged heterometallic Pt-Ir complexes: Tailoring excited states by taking the best of both worlds
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The CC-linkage of Pt(PR3)2(CCAr)2 with (CN)2Ir(NN)+ (CN = 2-phenylpyridine; NN = bipyridyl) leads to hetero-bi- and trimetallic species exhibiting photophysical properties reminiscent of both [Pt]- and [Ir]-containing moieties through the generation of a [Pt] → [Ir] charge transfer excited state. The Royal Society of Chemistry 2012.
- Soliman, Ahmed M.,Fortin, Daniel,Harvey, Pierre D.,Zysman-Colman, Eli
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supporting information; experimental part
p. 1120 - 1122
(2012/03/10)
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- Homoleptic zincate-promoted room-temperature halogen-metal exchange of bromopyridines
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Homoleptic lithium tri- and tetraalkyl zincates were reacted with a set of bromopyridines. Efficient and chemoselective bromine-metal exchanges were realized at room temperature with a substoichiometric amount of nBu 4ZnLi2·TMEDA reagent (1/3 equiv; TMEDA=N,N,N′,N′-tetramethylethylenediamine). This reactivity contrasted with that of tBu4ZnLi2·TMEDA, which was inefficient below one equivalent. DFT calculations allowed us to rationalize the formation of N...Li stabilized polypyridyl zincates in the reaction. The one-pot difunctionalization of dibromopyridines was also realized using the reagent stoichiometrically. The direct creation of C-Zn bonds in bromopyridines enabled us to perform efficient Negishi-type cross-couplings. Mild zincation! nBu4ZnLi2·TMEDA (in substoichiometric amounts) promoted efficient and chemoselective room-temperature bromine-metal exchange of a range of bromopyridines (see scheme). DFT calculations strongly supported the formation of a stabilized tripyridylzincate, which could be reacted with electrophiles or be directly involved in palladium-catalyzed cross-coupling reactions.
- Chau, Nguyet Trang Thanh,Meyer, Maxime,Komagawa, Shinsuke,Chevallier, Floris,Fort, Yves,Uchiyama, Masanobu,Mongin, Florence,Gros, Philippe C.
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experimental part
p. 12425 - 12433
(2011/01/05)
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- Studies towards the conception of new selective PPARβ/δ ligands
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In order to define new PPARβ/δ ligands, SAR study on the selective PPARβ/δ activator L-165,041 led to the identification of one key functional group for selective PPARβ/δ activation. Furthermore, taking advantage of SAR studies done elsewhere on the most selective PPARβ/δ ligand GW501516, the conception of new ligands showing good affinity for PPARβ/δ is reported. Finally, synthesis and biological evaluation of pyridine analogues have shown the benefical effect of the pyridine ring on the PPARβ/δ subtype selectivity.
- Ekambome Bassene, Carine,Suzenet, Franck,Hennuyer, Nathalie,Staels, Bart,Caignard, Daniel-Henri,Dacquet, Catherine,Renard, Pierre,Guillaumet, Gerald
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p. 4528 - 4532
(2007/10/03)
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- Aryl sulfonamide and sulfonyl compounds as modulators of PPAR and methods of treating metabolic disorders
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Aryl sulfonamide and sulfonyl compounds as modulators of peroxisome proliferator activated receptors, pharmaceutical compositions comprising the same, and methods of treating disease using the same are disclosed.
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Page/Page column 73
(2010/02/14)
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- Synthesis of 5-bromopyridyl-2-magnesium chloride and its application in the synthesis of functionalized pyridines
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(Chemical Equation Presented) The 5-bromopyridyl-2-magnesium chloride (2), which was not accessible previously, was efficiently synthesized for the first time via an iodomagnesium exchange reaction with 5-bromo-2-iodopyridine (1). This reactive intermediate was allowed to react with a variety of electrophiles to afford a range of useful functionalized pyridine derivatives. Application of this methodology to 5-bromo-2-iodo-3-picoline provided a simple and economical synthesis of a key intermediate for the preparation of Lonafarnib, a potent anticancer agent.
- Song, Jinhua J.,Yee, Nathan K.,Tan, Zhulin,Xu, Jinghua,Kapadia, Suresh R.,Senanayake, Chris H.
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p. 4905 - 4907
(2007/10/03)
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- Synthesis of heteroarylamine intermediate compounds
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Disclosed are novel 2-(5-halopyridyl) and 2-(5-halopyrimidinyl) magnesium halides, processes of making and their use in the efficient synthesis in their respective 5-halo-2-substituted pyridines and pyrimidines.
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- Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids
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As part of a case study, rational strategies for the preparation of all ten 2-, 3-, or 4-pyridinecarboxylic acids and all nine 2-, 3-, 4-, or 8-quinolinecarboxylic acids bearing trifluoromethyl substituents at the 2-, 3-, or 4-position were elaborated. The trifluoromethyl group, if not already present in the precursor, was introduced either by the deoxygenative fluorination of suitable carboxylic acids with sulfur tetrafluoride or by the displacement of ring-bound bromine or iodine by trifluoromethylcopper generated in situ. The carboxy function was produced by treatment of organolithium or organomagnesium intermediates, products of halogen/metal or hydrogen/ metal permutation, with carbon dioxide. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
- Cottet, Fabrice,Marull, Marc,Lefebvre, Olivier,Schlosser, Manfred
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p. 1559 - 1568
(2007/10/03)
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- Synthesis of heteroarylamine intermediate compounds
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Disclosed are novel 2-(5-halopyridyl) and 2-(5-halopyrimidinyl) magnesium halides, processes of making and their use in the efficient synthesis in their respective 5-halo-2-substituted pyridines and pyrimidines.
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- Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters
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This paper describes a general method for the synthesis and isolation of novel 6-halo-pyridin-3-yl-boronic acids and esters 2-5. These compounds are prepared taking in account a regioselective halogen-metal exchange with a trialkylborate starting from 2,5-dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalysed coupling with a range of arylhalides and authorise a strategy to produce new pyridines libraries.
- Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valérie,Bovy, Philippe R,Rault, Sylvain
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p. 2885 - 2890
(2007/10/03)
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- Novel synthesis of heteroarylamine intermediate compounds
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Disclosed are novel 2-(5-halopyridyl) and 2-(5-halopyrimidinyl) magnesium halides, processes of making and their use in the efficient synthesis in their respective 5-halo-2-substituted pyridines and pyrimidines.
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- A shape-persistent macrocycle with two opposing 2,2':6',2'-Terpyridine units
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The synthesis reported here of the shape-persistent macrocycle 9 with two opposing terpyridine units, and with pendant flexible chains for solubility reasons, was achieved by Suzuki cross-coupling of two 'half-cycles', the bisboronic acid ester 7 and its diiodo counterpart 8. Cycle 9 was obtained on a 100 mg scale in a yield of 20%. It was characterized by FAB mass spectrometry and 1H and 13C NMR spectroscopy. Cycle 9 is the first shape-persistent cycle containing terpyridine units that is larger than cyclosexipyridine. An improved synthesis of the important building block dibromoterpyridine 12 is also presented.
- Lehmann, Uwe,Dieter Schlueter
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p. 3483 - 3487
(2007/10/03)
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