- New Tricks by Old Anions: Hydrogen Bonded Hexacyanoferrous Anionic Networks
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Hexacyanoferrates are well-known to form metal?organic frameworks by coordination to metal atoms or acting as hydrogen bond acceptors. In this paper we report a new type of hexacyanoferrate self-assembly, based on direct hydrogen bonding of partially protonated hexacyanoferrate anions. By preparing a series of 15 hexacyanoferrates with various organic bases, we have found that protonated hexacyanoferrates (present in 10 structures) readily form chains (two structures), two-dimensional (four structures), or three-dimensional networks (four structures), whereby the dimensionality of the network generally increases with the protonation degree of the hexacyanoferrates. The exact mode of the self-assembly, including the network type, depends on fine interplay of the pKa value of the base, its steric properties, and the stoichiometry of the formed solid.
- Cvrtila, Ivica,Stilinovic, Vladimir
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- Linear-shaped thermally activated delayed fluorescence emitter using 1,5-naphthyridine as an electron acceptor for efficient light extraction
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In this study, we developed a donor-π-acceptor-π-donor-type thermally activated delayed fluorescence (TADF) emitter (NyDPAc) using 1,5-naphthyridine as a core moiety. NyDPAc exhibited a high horizontal dipole ratio and thus a high external quantum efficiency (20.9%) even at a relatively low photoluminescence quantum yield (57%). 1,5-naphthyridine as an electron acceptor represents a promising core moiety for efficient TADF materials.
- Lee, Youngnam,Woo, Seung-Je,Kim, Jang-Joo,Hong, Jong-In
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- Electrochemical investigation of structurally varied azinium scaffolds
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Inspired by the successful utilization of aziniums as anolytes in redox-flow batteries, we have designed and prepared a systematically extended series of (di)azinium compounds based on pyrazine, bipyridine, 1,5-naphthyridine, 3,8-phenanthroline, (E)-4,4′-
- Bure?, Filip,Bure?ová, Zuzana,Klikar, Milan,Kví?ala, Jaroslav,Mazúr, Petr,Mike?ová, Michaela,Rak, Kamil
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supporting information
p. 8830 - 8839
(2021/10/22)
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- One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes
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The transition metal-free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis-diazanaphthalenes were synthesized in moderate to high yield by homo- and cross-coupling of related monomers. In addition, the single-step synthesis of diquinoxalino [2,3-a: 2', 3'c] phenazine and 2,2': 3', 2″ - terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.
- Ucar, Sefa,Dastan, Arif
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supporting information
p. 4013 - 4022
(2020/09/21)
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- Zn-, Mg-, and Li-TMP Bases for the Successive Regioselective Metalations of the 1,5-Naphthyridine Scaffold (TMP=2,2,6,6-Tetramethylpiperidyl)
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A set of successive regioselective metalations and functionalizations of the 1,5-naphthyridine scaffold are described. A combination of Zn-, Mg-, and Li-TMP (TMP=2,2,6,6-tetramethylpiperidyl) bases and the presence or absence of a Lewis acid (BF3?OEt2) allows the introduction of up to three substituents to the 1,5-naphthyridine core. Also, a novel “halogen dance” reaction was discovered upon metalation of an 8-iodo-2,4-trifunctionalized 1,5-naphthyridine allowing a fourth regioselective functionalization. Additionally, reactions leading to key 1,5-naphthyridines for the preparation of OLED materials and a potential antibacterial agent were performed.
- Balkenhohl, Moritz,Greiner, Robert,Makarov, Ilya S.,Heinz, Benjamin,Karaghiosoff, Konstantin,Zipse, Hendrik,Knochel, Paul
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supporting information
p. 13046 - 13050
(2017/09/06)
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- Design and synthesis of novel substituted naphthyridines as potential c-Met kinase inhibitors based on MK-2461
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Abstract Two series of novel 1,5-naphthyridine and 1,6-naphthyridine derivatives were designed and synthesized based on the c-Met kinase inhibitor MK-2461 under the guidance of scaffold hopping strategy. All were tested on c-Met kinase and in vitro anti-tumor activities against Hela and A549 cell lines. The results indicated that 1,6-naphthyridine was a more promising c-Met inhibitory structure core compared with 1,5-naphthyridine. Among them, 26b and 26c showed the best enzymic and cytotoxic activities. The western blot experiments implied that the cytotoxic activity of 26c might be partially through suppressing the phosphorylation of c-Met kinase.
- Wu, Jing-Fang,Liu, Ming-Ming,Huang, Shao-Xu,Wang, Yang
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supporting information
p. 3251 - 3255
(2015/07/08)
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- Iodine- and indium(III) chloride-catalyzed facile syntheses of 1,5- and 1,8-naphthyridines
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Iodine- and InCl3-catalyzed facile syntheses of 1,5- and 1,8-naphthyridines from 3-aminopyridine and 2-aminopyridines are described. The catalyst InCl3 could be recovered and reused up to five times efficiently.
- Chunavala, Kaushik C.,Adimurthy, Subbarayappa
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scheme or table
p. 1843 - 1851
(2011/06/23)
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- Intramolecular inverse-electron-demand Diels-Alder reactions of imidazoles with 1,2,4-triazines: A new route to 1,2,3,4-tetrahydro-1,5-naphthyridines and related heterocycles
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The intramolecular inverse-electron-demand Diels-Alder reaction between imidazoles and 1,2,4-triazines linked by a trimethylene tether from the imidazole N1 position to the triazine C3 proceed in excellent yields to produce 1,2,3,4-tetrahydro-1,5-naphthyridines. The reaction proceeds by a cycloaddition with subsequent loss of nitrogen, followed by a presumed stepwise loss of a nitrile. The analogous intramolecular cycloadditions employing a tetramethylene tether also proceeded to give 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines in acceptable yields. The reaction to produce the tetrahydro-1,5-naphthyridines can also be promoted with microwave irradiation.
- Lahue, Brian R.,Lo, Sie-Mun,Wan, Zhao-Kui,Woo, Grace H. C.,Snyder, John K.
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p. 7171 - 7182
(2007/10/03)
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- Unusual oxidative rearrangement of 1,5-diazadecalin
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Upon treatment with (PhIO)n or PhI(OAc)2, 1,5-diaza-cis-decalin undergoes oxidation at the more hindered position along with fragmentation to yield the ring-expanded bislactam. The cis and trans 1,5-diazadecalins both undergo the sam
- Li, Xiaolin,Xu, Zhenrong,DiMauro, Erin F,Kozlowski, Marisa C
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p. 3747 - 3750
(2007/10/03)
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- Synthesis and resolution of a novel chiral diamine ligand and application to asymmetric lithiation-substitution
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(equation presented) A short, efficient synthesis of chiral 1,5-diaza-cis-decalins (7) is presented. In the lithiation of N-Boc pyrrolidine, the ligands with the smallest most electron rich R groups (Me > Et > CH2tBu > CH2CF3 ≈ Bn) were most effective. In the asymmetric deprotonation/substitution of benzylic substrates, (R,R)-7 (R = Me, R′ = H) conferred modest selectivity. The ready availability of both enantiomers of the 1,5-diaza-cis-decalins and the ability to tune steric and electronic properties renders these compounds an attractive new class of diamine ligands.
- Li, Xiaolin,Schenkel, Laurie B.,Kozlowski, Marisa C.
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p. 875 - 878
(2007/10/03)
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- Dienophilicity of imidazole in inverse electron demand Diels-Alder reactions; intramolecular reactions with 1,2,4-triazines
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Imidazole and 2-phenylimidazole undergo intramolecular cycloadditions with 1,2,4-triazines tethered between an imidazole nitrogen and the triazinyl C3 position with a trimethylene chain to produce tetrahydro-1,5-naphthyridines following loss of N2/s
- Neipp, Christopher E.,Ranslow, Peter B.,Wan, Zhaokui,Snyder, John K.
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p. 7499 - 7502
(2007/10/03)
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- Novel indolo [3,2,1-de] [1,4] oxazino [2,3,4-ij] [1,5]
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Novel compounds selected from the group consisting of all possible racemic or optically active forms of compounds of the formula STR1 wherein R1 and R2 are individually selected from the group consisting of hydrogen, alkyl and alkoxy of 1 to 5 carbon atoms, -OH, -CF3 and -NO2 and STR2 is selected from the group consisting of STR3 and their non-toxic, pharmaceutically acceptable acid addition salts having a very good analgesic activity as well as antidepressive, neuronal protective, anti-anoxic, anti-ischemic and no-otropic activities.
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- Certain 1-carbothioamides of 1,5-naphthyridine derivatives
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The invention relates to thioureas which are derivatives of 1,5-Naphthyridines. The compounds are anti-ulcer agents or intermediates therefor.
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- Certain 1-(N-acyl)-carbothioamides of 1,5-naphthyridine derivatives
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The invention relates to N-acyl thioureas which are derivatives of 1,5-Naphthyridines. The compounds are intermediates for anti-ulcer agents.
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- Certain 1-carbothioamides of 1,8-naphthyridines, pyrrolo(2,3-b)pyridines and pyrido(2,3-b)azepines
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The invention relates to thioureas which are derivatives of organic nitrogen compounds containing a pyridine ring to which is fused a saturated nitrogen containing ring which carries on its nitrogen atom a thioamide or substituted thioamide group. The compounds are anti-ulcer agents or intermediates therefor.
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