154824-10-9Relevant academic research and scientific papers
Synthesis and TNF expression inhibitory properties of new thalidomide analogues derived via Heck cross coupling
Stewart, Scott G.,Spagnolo, Daniel,Polomska, Marta E.,Sin, Melvin,Karimi, Mahdad,Abraham, Lawrence J.
, p. 5819 - 5824 (2007)
A library of new thalidomide analogues containing an olefin functionality were synthesised using a Heck cross coupling reaction from their aryl halogenated precursor. All analogues were tested for their ability to inhibit the synthesis of the proinflammatory cytokine Tumour Necrosis Factor (TNF). Compounds 22, 29, 33 and 37 were the most effective in this assay inhibiting TNF expression 50%, 69%, 52% and 50%, respectively. Crown Copyright
Synthesis of 3,4-fused 2-quinolones from an (ortho-aminophenyl)propiolate via sequential cycloaddition/lactam formation
Murayama, Tsukasa,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 690 - 694 (2015/03/18)
An N-phthalimide-protected (ortho-aminophenyl)propiolate was prepared by the carboxylation of the corresponding silylalkyne precursor with carbon dioxide. The obtained propiolate was further transformed to various 3,4-fused 2-quinolones via cycloadditions and subsequent deprotection/lactam formation.
Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
Jha, Amitabh,Chou, Ting-Yi,ALJaroudi, Zainab,Ellis, Bobby D.,Cameron, T. Stanley
supporting information, p. 848 - 857 (2014/05/06)
The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
Metal-free oxidation/C(sp3)iH functionalization of unactivated alkynes using pyridine-N-oxide as the external oxidant
Chen, Dian-Feng,Han, Zhi-Yong,He, Yu-Ping,Yu, Jie,Gong, Liu-Zhu
supporting information, p. 12307 - 12310 (2013/02/22)
Externally yours: 2,3-Dihydroquinolin-4(1H)-ones are obtained in moderate to good yields (40-84 %, see scheme) in a metal-free oxidation/C(sp 3)iH functionalization of unactivated aryl alkynes. 2,6-Dichloropyridine-N-oxide is used as an external oxidant. In the reaction, a Bronsted acid, not a metal, plays a key role in the triple CiC bond activation. Copyright
