- Photochemistry of phenyl azides bearing 2-hydroxy and 2-amino groups studied by matrix-isolation spectroscopy: Generation and characterization of reactive o-quinoid compounds
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Broad-band irradiation (λ > 370 nm) of 2-hydroxyphenyl azide (1) in Ar at 10 K monitored by IR resulted in the formation of at least three major products, all of which were shown to be photointerconvertible under these conditions. The two products showing
- Tomioka, Hideo,Matsushita, Takeshi,Murata, Shigeru,Koseki, Shiro
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- Template synthesis of benzannulated N-heterocyclic carbene ligands
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The reaction of 2-azidophenyl isocyanide (7) with [M(CO)5(thf)] (M = Cr, W) yields the isocyanide complexes [M(CO)5(7)] (M = Cr 8, M = W 9). Complexes 8 and 9 react with tertiary phosphines such as triphenylphosphane at the azido fun
- Hahn, F. Ekkehardt,Langenhahn, Volker,Meier, Nicole,Luegger, Thomas,Fehlhammer, Wolf Peter
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- Fragment-Based Discovery of a Qualified Hit Targeting the Latency-Associated Nuclear Antigen of the Oncogenic Kaposi's Sarcoma-Associated Herpesvirus/Human Herpesvirus 8
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The latency-associated nuclear antigen (LANA) is required for latent replication and persistence of Kaposi's sarcoma-associated herpesvirus/human herpesvirus 8. It acts via replicating and tethering the virus episome to the host chromatin and exerts other functions. We conceived a new approach for the discovery of antiviral drugs to inhibit the interaction between LANA and the viral genome. We applied a biophysical screening cascade and identified the first LANA binders from small, structurally diverse compound libraries. Starting from a fragment-sized scaffold, we generated optimized hits via fragment growing using a dedicated fluorescence-polarization-based assay as the structure-activity-relationship driver. We improved compound potency to the double-digit micromolar range. Importantly, we qualified the resulting hit through orthogonal methods employing EMSA, STD-NMR, and MST methodologies. This optimized hit provides an ideal starting point for subsequent hit-to-lead campaigns providing evident target-binding, suitable ligand efficiencies, and favorable physicochemical properties.
- Kirsch, Philine,Jakob, Valentin,Oberhausen, Kevin,Stein, Saskia C.,Cucarro, Ivano,Schulz, Thomas F.,Empting, Martin
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p. 3924 - 3939
(2019/05/06)
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- Room-temperature Cu(ii)-catalyzed aromatic C-H azidation for the synthesis of ortho-azido anilines with excellent regioselectivity
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Cu(ii)-catalyzed aromatic C-H azidation with azido-benziodoxolone under mild conditions has been described. The primary amine exhibits an excellent ortho-directing effect, providing ortho-azidated anilines as the sole products. the Partner Organisations 2014.
- Fan, Yunpeng,Wan, Wen,Ma, Guobin,Gao, Wei,Jiang, Haizhen,Zhu, Shizheng,Hao, Jian
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supporting information
p. 5733 - 5736
(2014/05/20)
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- Copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate)-catalyzed coupling of sodium azide with aryl iodides/boronic acids to aryl azides or aryl amines
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This work reports an efficient protocol for the coupling reaction of aryl iodides/boronic acids with sodium azide to aryl azides/amines in the presence of copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate) Cu(TMHD)2 catalyst. The Cu(TMHD)2 catalyst is a structurally well-defined, O-containing, air- and moisture-stable, transition-metal complex and works at mild reaction conditions. It was observed that aryl azides can be reduced further to corresponding aniline derivatives using the same catalyst under basic reaction conditions for a prolonged period. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Lanke, Satish R.,Bhanage, Bhalchandra M.
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p. 399 - 407
(2014/01/06)
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- Copper-catalyzed C-H azidation of anilines under mild conditions
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A novel and efficient copper-catalyzed azidation reaction of anilines via C-H activation has been developed. This method, in which the primary amine acts as a directing group by coordinating to the metal center, provides ortho azidation products regioselectively under mild conditions. This effective route for the synthesis of aryl azides is of great significance in view of the versatile reactivity of the azide products.
- Tang, Conghui,Jiao, Ning
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supporting information
p. 18924 - 18927
(2013/01/15)
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- Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides
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(Chemical Equation Presented) The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.
- Shen, Meihua,Driver, Tom G.
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supporting information; experimental part
p. 3367 - 3370
(2009/05/27)
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- Pharmaceutical uses and synthesis of nicotinamides
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A compound of the formula and pharmaceutically acceptable salts thereof, wherein R1is selected from (R3)C(═O)—N(R4)— and (R3)(R4)N—C(═O)—; R2is selected from —OR5and —N(R5)(R6); n is 0, 1, 2 or 3; X is selected from oxygen and sulfur; and R3, R4, R5and R6are independently selected from hydrogen, alkyl, heteroalkyl, aryl, aryl(akylene), heteroaryl, heteroaryl(alkylene), carbocycle, carbocycle(alkylene), heterocycle, and heterocycle(alkylene); as well as pharmaceutical compositions containing said compound. The compounds and compositions are useful in, for example, the treatment of inflammatory events in an animal subject.
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Page/Page column 25-26
(2010/02/08)
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- THE REACTION OF ORTHO-SUBSTITUTED AROMATIC AZIDES WITH BORON TRICHLORIDE OR TRIFLUORIDE
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The reactiont of boron trichloride or trifluoride with ortho-aryl, -diazoaryl, and -arylazoaryl phenyl azides in benzene at room temperature generally gives fused azoles in high yields.Treatment of 2-nitrophenyl azide with boron trichloride mainly affords chlorinated nitroanilines, whereas with boron trifluoride it gives N-o-nitrophenylaniline.In aromatic solvents at 60 deg C in the presence of boron trifluoride-diethyl ether, 2-azidobiphenyl forms carbazole and 2-(arylamino)biphenyls, the formation of which depends greatly upon the nucleophilicity of the solvent used; however, its pseudo-first-order decomposition rate is slightly greater in benzene than in toluene or m-xylene.Under the same conditions, phenyl azide forms diarylamines.The results suggest that singlet nitrenium ions, arising from the corresponding azidetrihalogenoborane complexes by loss of molecular nitrogen, are generally the reactive intermediates.
- Spagnolo, Piero,Zanirato, Paolo
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p. 2615 - 2620
(2007/10/02)
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