1331850-50-0Relevant articles and documents
Deprotonative Metalation of Methoxy-Substituted Arenes Using Lithium 2,2,6,6-Tetramethylpiperidide: Experimental and Computational Study
Akimoto, Gaku,Otsuka, Mai,Takita, Ryo,Uchiyama, Masanobu,Hedidi, Madani,Bentabed-Ababsa, Ghenia,Lassagne, Frédéric,Erb, William,Mongin, Florence
, p. 13498 - 13506 (2018)
The reaction pathways of lithium 2,2,6,6-tetramethylpiperidide (LiTMP)-mediated deprotonative metalation of methoxy-substituted arenes were investigated. Importantly, it was experimentally observed that, whereas TMEDA has no effect on the course of the reactions, the presence of more than the stoichiometric amount of LiCl is deleterious, in particular without an in situ trap. These effects were corroborated by the DFT calculations. The reaction mechanisms, such as the structure of the active species in the deprotonation event, the reaction pathways by each postulated LiTMP complex, the stabilization effects by in situ trapping using zinc species, and some kinetic interpretation, are discussed herein.
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.
AZEPANE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS
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Paragraph 0337; 0338, (2015/05/26)
Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.
