93560-55-5Relevant articles and documents
Solid-state fluorescence of zwitterionic imidazolium pyridinolates bearing long alkyl chains: Control of emission properties based on variation of lamellar alignment
Yoshida, Atsushi,Ikeshita, Masahiro,Komiya, Naruyoshi,Naota, Takeshi
, p. 6000 - 6007 (2017/09/18)
Herein, the control of the crystalline-state fluorescence of zwitterionic imidazolium 2-pyridin-3-olate 1 bearing linear alkyl chains via morphological variations is described, along with a mechanistic rationale. Crystals of 1a–e prepared from CH3CN exhibited intense blue fluorescence under UV irradiation at 298 K, whereas crystals of 1e prepared from i-PrOH/Et2O were less emissive under the same measurement conditions. Temperature-dependent emission spectra showed that emissive crystals of 1a–e experienced minimal emission decay with increasing temperature, whereas crystalline 1e, having a different polymorphism, was highly heat-quenchable. Single-crystal XRD established that less emissive, heat-quenchable crystal 1e had a lamellar structure supported by consecutive face-to-face arrangement with π-stacking interactions between imidazolium and pyridinolate moieties, whereas highly emissive, heat-resistant crystals 1d and 1e had a face-to-edge lamellar structure with CH-π interactions between the heteroaromatic rings.
Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells
Hedidi, Madani,Erb, William,Bentabed-Ababsa, Ghenia,Chevallier, Floris,Picot, Laurent,Thiéry, Valérie,Bach, Stéphane,Ruchaud, Sandrine,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence
, p. 6467 - 6476 (2016/09/23)
N-Arylation of pyrrole with 3-iodo-4-methoxypyridine was investigated by copper catalysis under different conditions. The best conditions, that proved to be protocol A (CuI, DMEDA or TMEDA, K3PO4, DMF at 110?°C) and above all protocol B (Cu2O, Cs2CO3, DMSO at 110?°C), were applied to the synthesis of various N-(methoxypyridyl) pyrroles, indoles and benzimidazoles. The behavior of the different iodinated methoxypyridines was rationalized by evaluating the partial positive charge on the carbon bearing iodine from the1H NMR chemical shift of the corresponding deiodinated substrates. The reaction was next connected with the deprotometalation-iodolysis step generating iodinated methoxypyridines: straight involvement of the crude iodo intermediates in pyrrole N-arylation afforded the expected N-(methoxypyridyl) pyrroles in good yields. Several synthesized N-(methoxypyridyl) azoles exerted low to moderate antiproliferative activity in A2058 melanoma cells.
A general method for copper-catalyzed arene cross-dimerization
Do, Hien-Quang,Daugulis, Olafs
supporting information; experimental part, p. 13577 - 13586 (2011/10/10)
A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bon