18004-57-4Relevant articles and documents
Solvent-dependent effect by carbon dioxide on the photoreactions of (9-anthryl)alkylamines
Horiguchi, Masahiro,Ito, Yoshikatsu
, p. 12286 - 12293 (2007)
The effect of CO2 on a photoreaction was first studied systematically by using (9-anthryl)alkylamines (APA, AEA, and AMA) as the starting compound. From close scrutiny of the results, the CO2 effect was clearly observed and was well rationalized by the previously reported novel solvent dependence of the amine-CO2 reversible reactions. For instance, the yield of the dimer (h-t from APA or AEA, h-t+h-h from AMA) obtained in MeOH or DMSO was higher under CO2 than under argon and this was ascribed to formation of either ammonium bicarbonate/carbonate in MeOH or carbamic acid in DMSO, which will prevent the nitrogen lone pair from being involved in electron-transfer reactions. In fact, the electron-transfer side reactions producing 1-3 in DMSO were strongly inhibited under CO2. Also, due to formation of noncovalent linkage between the ammonium cation and the carbamate anion in 2-PrOH, the proportion of h-h relative to h-t produced from AMA in 2-PrOH was increased by carrying out the reaction under CO2.
A catalytic regioselective procedure for the synthesis of aryl oximes in the presence of palladium nanoparticles
Demir, Emine,Goksu, Haydar,Orhan, Ersin
, (2022/01/20)
The synthesis of aryl oximes from aryl aldehyde derivatives was carried out using hydroxylamine hydrochloride and aluminum oxy hydroxide-supported palladium (Pd/AlO(OH) nanoparticles. The procedure is revealed via the regioselective synthesis of oxime der
Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction
Pan, Hongmei,Lu, Tong,Wu, Xuedan,Gu, Chengwen,Tao, Naili,Zhang, Biao,Wang, Ao,Chen, Guangmei,Zhang, Kehua,Cheng, Jie,Jin, Jie
supporting information, p. 2360 - 2364 (2019/11/11)
A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.
Exploring isoxazoles and pyrrolidinones decorated with the 4,6-dimethoxy-1,3,5-triazine unit as human farnesyltransferase inhibitors
Lucescu, Liliana,Ghinet, Alina,Shova, Sergiu,Magnez, Romain,Thuru, Xavier,Farce, Amaury,Rigo, Beno?t,Belei, Dalila,Dubois, Jo?lle,B?cu, Elena
, (2019/04/13)
Unprecedented triazinyl-isoxazoles were afforded via an effective cycloaddition reaction between nitrile oxides and the scarcely described 2-ethynyl-4,6-dimethoxy-1,3,5-triazine as dipolarophile. The biological evaluation of the newly synthesized compounds showed that the inhibition of human farnesyltransferase by zinc complexation could be improved with triazine-isoxazole moieties. The replacement of the isoxazole unit by a pyrrolidin-2-one was detrimental to the inhibitory activity while the pyrrolidin-2-thione derivatives conserved the biological potential. The potential of selected compounds to disrupt protein farnesylation in Chinese hamster ovary (CHO) cells transfected with pEGFP-CAAX was also evaluated.
