18523-44-9Relevant articles and documents
Detection of pentazolate anion (cyclo-N5-) from laser ionization and decomposition of solid p-dimethylaminophenylpentazole
?stmark, Henric,Wallin, Sara,Brinck, Tore,Carlqvist, Peter,Claridge, Rob,Hedlund, Emma,Yudina, Larisa
, p. 539 - 546 (2003)
Laser desorption ionization (LDI) time-of-flight (TOF) mass spectroscopy of solid p-dimethylaminophenylpentazole (1) gives strong peaks of m/z -42 and -70. The -70 peak was identified by 15N labeling of 1 to be the pentazolate anion (cyclo-N5-). The pentazolate anion is formed by an electron attachment to 1 forming the corresponding radical anion followed by a decomposition into 4-N(CH3)2-C 6H4· and (cyclo-N5-). The LDI TOF experimental study also revealed that the (cyclo-N5 -) is very stable. These conclusions are supported by QM calculations at the B3LYP/6-311+G(2df,p) level.
Picosecond and Nanosecond Laser Photolyses of p-(Dimethylamino)phenyl Azide in Solution
Kobayashi, Takayoshi,Ohtani, Hiroyuki,Suzuki, Kaoru,Yamaoka, Tsuguo
, p. 776 - 779 (1985)
Photodissociation of p-(dimethylamino)phenyl azide (DMAPA) in toluene at room temperature takes a place from the excited singlet state of azide within 6 ps.A transient absorption spectrum of a precursor of the relevant nitrene, p-(dimethylamino)phenylnitr
Solution photochemistry of [ p -(Dimethylamino)phenyl]pentazole (DMAPP) at 193 and 300 nm
Bazanov,Haas
, p. 2661 - 2671 (2015)
The photochemistry of [p-(dimethylamino)phenyl]pentazole (DMAPP) at 193 nm and in the near UV is reported, with emphasis on the nature of the final stable products. The (dimethylamino)phenyl azide (DMAPA) is found as a major product in MeCN, but not in dichloromethane (DCM). (In this paper the acronyms DMAPP and DMAPA refer to the para isomers.) The photochemistry of DMAPA is also explored for comparison. The data obtained in MeCN solutions are consistent with the initial formation of the corresponding nitrene, but in DCM, different products are found, on the basis of NMR data. In the case of high reactant concentration in DCM (10-2 M), quantitative conversion of DMAPP and DMAPA is observed, indicating a high quantum yield. In contrast, MeCN solutions react much more slowly. A radical-type chain reaction mechanism is proposed to account for this observation. At high dilution, DMAPP is completely converted to products in both solvents. Possible mechanisms accounting for these results are discussed.
Synthesis and spectral properties of 6′-triazolyl-dihydroxanthene-hemicyanine fused near-infrared dyes
Gu, Lingyue,Renault, Kévin,Romieu, Anthony,Richard, Jean-Alexandre,Srinivasan, Rajavel
, p. 12208 - 12215 (2020)
We describe the synthesis of a range of 6′-triazolyl-dihydroxanthene-hemicyanine (DHX-hemicyanine) fused dyes through an effective copper-catalyzed azide-alkyne cycloaddition (CuAAC) "click"reaction, with the aim of providing molecular diversity and evaluating the spectral properties of these near-infrared (NIR)-active materials. This was implemented by reacting 15 different aliphatic and aromatic azides with a terminal alkynyl-based DHX-hemicyanine hybrid scaffold prepared in four steps and 35% overall yield from 4-bromosalicylaldehyde. The resulting triazole derivatives have been fully characterized and their optical properties determined both in organic solvents and under simulated physiological conditions (phosphate buffered saline containing 5% of bovine serum albumin protein). This systematic study is a first important step towards the development of NIR-I fluorogenic "click-on"dyes or related photoactive agents for light-based diagnostic and/or therapeutic applications.
A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide
Babin, Victor,Sallustrau, Antoine,Loreau, Olivier,Caillé, Fabien,Goudet, Amélie,Cahuzac, Hélo?se,Del Vecchio, Antonio,Taran, Frédéric,Audisio, Davide
supporting information, p. 6680 - 6683 (2021/07/12)
Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including14C and11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.
Tetrazastannoles versus distannadiazanes-a question of the tin(ii) source
Schulz, Axel,Thomas, Max,Villinger, Alexander
supporting information, p. 125 - 132 (2019/01/04)
Various tin(ii) compounds such as Mes*2Sn (Mes* = 2,4,6-tri-tert-butylphenyl), Sn[N(SiMe3)2]2 and TerSnCl (Ter = 2,6-bis(2,4,6-trimethylphenyl)phenyl) could be readily oxidised by organic azides to release N2, forming nitrogen-tin compounds. Depending on the used Sn(ii) compound, the reactions with two equivalents of azide led to the formation of tetrazastannoles (R2N4SnR′2) or cyclo-distannadiazanes [R2Sn(μ-NR′)]2. The reactivity was independent of the electronic situation of the organic azide. Additionally, Mes*2Sn formed an amido-azido compound of the type R(R′)Sn(N(SiMe3)2)N3 in the presence of Me3SiN3. Presumably, the corresponding tetrazastannole was formed in the first step followed by a ring opening reaction. The same holds true for the reaction of Sn[N(SiMe3)2]2 with Me3SiN3 while TerSnCl showed no reaction in the presence of Me3SiN3, even after prolonged heating.
Catalytic Azoarene Synthesis from Aryl Azides Enabled by a Dinuclear Ni Complex
Powers, Ian G.,Andjaba, John M.,Luo, Xuyi,Mei, Jianguo,Uyeda, Christopher
supporting information, p. 4110 - 4118 (2018/03/29)
Azoarenes are valuable chromophores that have been extensively incorporated as photoswitchable elements in molecular machines and biologically active compounds. Here, we report a catalytic nitrene dimerization reaction that provides access to structurally and electronically diverse azoarenes. The reaction utilizes aryl azides as nitrene precursors and generates only gaseous N2 as a byproduct. By circumventing the use of a stoichiometric redox reagent, a broad range of organic functional groups are tolerated, and common byproducts of current methods are avoided. A catalyst featuring a Ni - Ni bond is found to be uniquely effective relative to those containing only a single Ni center. The mechanistic origins of this nuclearity effect are described.
Synthesis, pharmacological evaluation and molecular modeling studies of triazole containing dopamine D3 receptor ligands
Peng, Xin,Wang, Qi,Mishra, Yogesh,Xu, Jinbin,Reichert, David E.,Malik, Maninder,Taylor, Michelle,Luedtke, Robert R.,Mach, Robert H.
supporting information, p. 519 - 523 (2015/03/05)
A series of 2-methoxyphenyl piperazine analogues containing a triazole ring were synthesized and their in vitro binding affinities at human dopamine D2 and D3 receptors were evaluated. Compounds 5b, 5c, 5d, and 4g, demonstrate high a
Differential Targeting of Human Topoisomerase II Isoforms with Small Molecules
Mariani, Angelica,Bartoli, Alexandra,Atwal, Mandeep,Lee, Ka C.,Austin, Caroline A.,Rodriguez, Rapha?l
supporting information, p. 4851 - 4856 (2015/06/25)
(Chemical Equation Presented). The TOP2 poison etoposide has been implicated in the generation of secondary malignancies during cancer treatment. Structural similarities between TOP2 isoforms challenge the rational design of isoform-specific poisons to further delineate these processes. Herein, we describe the synthesis and biological evaluation of a focused library of etoposide analogues, with the identification of two novel small molecules exhibiting TOP2B-dependent toxicity. Our findings pave the way toward studying isoform-specific cellular processes by means of small molecule intervention.
Syntheses and structure-activity relationships for some triazolyl p38α MAPK inhibitors
Seerden, Jean-Paul G.,Leusink-Ionescu, Gabriela,Leguijt, Robin,Saccavini, Catherine,Gelens, Edith,Dros, Bas,Woudenberg-Vrenken, Titia,Molema, Grietje,Kamps, Jan A.A.M.,Kellogg, Richard M.
, p. 1352 - 1357 (2014/03/21)
The design, synthesis and biological evaluation of novel triazolyl p38α MAPK inhibitors with improved water solubility for formulation in cationic liposomes (SAINT-O-Somes) targeted at diseased endothelial cells is described. Water-solubilizing groups wer
