2876-78-0Relevant articles and documents
Palladium-catalyzed cascade synthesis of spirocyclic oxindoles via regioselective C2-H arylation and C8-H alkylation of naphthalene ring
Luo, Xiai,Li, Wenguang,Lu, Haiyan,Deng, Guobo,Yang, Yuan,Yang, Chunming,Liang, Yun
, p. 713 - 716 (2021)
A simultaneous C2-H arylation and C8-H alkylation of naphthalene ring has been achieved by palladium-catalyzed cascade reaction of N-(2-halophenyl)-2-(naphthalen-1-yl)acrylamides with aryl iodides, which provides an efficient method for synthesizing various aryl-substituted spirocyclic oxindoles. The protocol enables three C–C bonds formation via an intramolecular Heck reaction and sequentially regioselective C–H bond activation.
Synthesis of 9,10-bis(trifluoromethyl)benzobarrelenes through reaction of hexafluorobut-2-yne and substituted naphthalenes
Kremlev, Mikhail M.,Mushta, Oleksii I.,Yagupolskii, Yurii L.,Rusanova, Julia A.,Peng, Sheng,Petrov, Viacheslav
, (2020)
The cycloadducts 9,10-bis(trifluoromethyl)benzobarrelenes were prepared by the reaction of hexafluorobut-2-yne (HFB) with 1- and, 2- substituted naphthalenes in moderate to high yields. In most cases the reaction proceeds with the formation of two isomeric products derived from cycloaddition of HFB to different aromatic rings of the naphthalene system. The individual isomers were isolated by column chromatography and fully characterized. The basic hydrolysis of ester derivatives of the various 9,10-bis(trifluoromethyl)benzobarrelenes provided the corresponding acids.
Spectroscopic, microscopic and first rheological investigations in charge-transfer interaction induced organogels
Das, Rajat K.,Banerjee, Supratim,Raffy, Guillaume,Del Guerzo, Andre,Desvergne, Jean-Pierre,Maitra, Uday
, p. 7227 - 7235 (2010)
This article describes two-component charge-transfer interaction mediated organogels (CT-gels) derived from anthracene carboxamides obtained from 2-amino-2-hydroxymethyl-1,3-propanediol (TRIS), and 2,3-dialkoxyanthracenes as donors, with 2,4,7-trinitrofluorenone (TNF) as the common acceptor. We demonstrate the versatility of TNF as an electron acceptor in the formation of these gels. The effect of subtle changes in the donor structure on the gelation ability has been investigated by varying the alkyl chain length in the dialkoxyanthracene donors, and by varying the position of the TRIS substituent in the anthracene carboxamide donors. Distinct differences have been observed in the nature of the CT-gels based on these two kinds of anthracene donors. It has been reported in the literature that 2,3-dialkoxyanthracenes form gels on their own in various aliphatic hydrocarbons and alcohols for linear alkyl chains bearing at least 6 carbon atoms (C6). In the present study, it is shown that the CT-complex of these molecules with TNF is able to gel many alcoholic and a few hydrocarbon solvents. Also, in the presence of TNF, the 2,3-dialkoxyanthracenes (C4-C5) which were non-gelators on their own at ambient temperatures, form CT-gels in a number of alcohols. The other series of gelators discussed, the anthracene carboxamides, require the mandatory presence of TNF to form gels. This donor-acceptor complex forms gels in various aliphatic alcohols. Interestingly, the formation of these CT-gels requires rapid cooling in most of the cases. Thermal stability studies with both types of CT-gels indicate an optimum stoichiometry of 1:1 between the donor and the acceptor. Dynamic rheological experiments reveal these gels as viscoelastic soft materials, with the mechanical strength of these gels depending on the amount of TNF present. This provides a means to tune the strength of the gel by varying the doping concentration of the acceptor.
Structure-Activity Relationships of Benzamides and Isoindolines Designed as SARS-CoV Protease Inhibitors Effective against SARS-CoV-2
Welker, Armin,Kersten, Christian,Müller, Christin,Madhugiri, Ramakanth,Zimmer, Collin,Müller, Patrick,Zimmermann, Robert,Hammerschmidt, Stefan,Maus, Hannah,Ziebuhr, John,Sotriffer, Christoph,Schirmeister, Tanja
supporting information, p. 340 - 354 (2020/10/19)
Inhibition of coronavirus (CoV)-encoded papain-like cysteine proteases (PLpro) represents an attractive strategy to treat infections by these important human pathogens. Herein we report on structure-activity relationships (SAR) of the noncovalent active-site directed inhibitor (R)-5-amino-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide (2 b), which is known to bind into the S3 and S4 pockets of the SARS-CoV PLpro. Moreover, we report the discovery of isoindolines as a new class of potent PLpro inhibitors. The studies also provide a deeper understanding of the binding modes of this inhibitor class. Importantly, the inhibitors were also confirmed to inhibit SARS-CoV-2 replication in cell culture suggesting that, due to the high structural similarities of the target proteases, inhibitors identified against SARS-CoV PLpro are valuable starting points for the development of new pan-coronaviral inhibitors.
Magnesium chloride (MgCl2) catalyzed highly regioselective C-3 ring opening of 2,3 epoxy alcohols by N-nucleophile
Kumar, Amit,Panda, Gautam
supporting information, (2021/04/09)
We herein report Magnesium chloride (MgCl2) catalyzed first highly C3-selective ring-opening reaction of various 2,3-epoxy alcohols with assorted N-Nucleophiles and sodium azide to furnish 3-amino-1,2 diols and 3-azido-1,2 diols respectively in high yields under mild reaction conditions. This protocol attributes the use of catalytic amount of Magnesium chloride (MgCl2), simple reaction conditions, practical operation and broad functional group tolerance.
