115706-17-7Relevant academic research and scientific papers
Site-Selective Cross-Coupling of Remote Chlorides Enabled by Electrostatically Directed Palladium Catalysis
Golding, William A.,Pearce-Higgins, Robert,Phipps, Robert J.
supporting information, p. 13570 - 13574 (2018/10/20)
Control of site-selectivity in chemical reactions that occur remote from existing functionality remains a major challenge in synthetic chemistry. We describe a strategy that enables three of the most commonly used cross-coupling processes to occur with high site-selectivity on dichloroarenes that bear acidic functional groups. We have achieved this by repurposing an established sulfonylated phosphine ligand to exploit its inherent bifunctionality. Mechanistic studies suggest that the sulfonate group engages in attractive electrostatic interactions with the cation associated with the deprotonated substrate, guiding cross-coupling to the chloride at the arene meta position. This counterintuitive combination of anionic ligand and anionic substrate demonstrates an alternative design principle when considering the application of noncovalent interactions to direct catalysis.
Comparison of Phenylacetates with Benzoates and Phenylpropanoates as Antifeedants for the Pine Weevil, Hylobius abietis
Unelius, C. Rikard,Bohman, Bj?rn,Nordlander, G?ran
, p. 11797 - 11805 (2018/11/21)
This study concludes an extensive investigation of antifeedants for the pine weevil, Hylobius abietis (Coleoptera: Curculionidae), an economically important pest of planted conifer seedlings. Building on the previously reported antifeedant effects of benzoates and phenylpropanoids (aromatic compounds with one- or three-carbon-atom substituents on the benzene ring), we here report the antifeedant effects of compounds with two-carbon-atom side chains (i.e., phenylacetates). We also present new results; the best antifeedants from the benzoate class were tested at 10-fold lower concentrations in order to find the optimal antifeedants. Generally, for all three compound classes, efficient antifeedants were found to have one or two methyl, chloro, or methoxy substituents on the aromatic ring. For monosubstituted phenylpropanoids, the substituent preferably should be in the para-position. In the search for synergistic antifeedant effects among the three compound classes, combinations of compounds from the three classes were tested in binary and ternary mixtures.
Iron(III)-Catalyzed Ortho-Preferred Radical Nucleophilic Alkylation of Electron-Deficient Arenes
Yu, Fei,Wang, Ting,Zhou, Huan,Li, Yajun,Zhang, Xinhao,Bao, Hongli
supporting information, p. 6538 - 6541 (2017/12/26)
The untraditional iron-catalyzed, ortho-preferred, radical alkylation of electron-deficient (hetero)arenes is reported. A variety of electron-deficient arenes were shown to react with various primary alkyl sources, producing the alkylated (hetero)arenes in good yields. This reaction might be an alkyl radical, nucleophilic aromatic substitution reaction, rather than the traditional electrophilic Friedel-Crafts reaction. HOMO-LUMO analysis and DFT studies on the key transition states underlying the regioselectivity are consistent with the observed reactions and the conclusions.
PYRIDO- AND PYRIMIDO (1, 2-A) PYRIMIDINE COMPOUNDS USEFUL AS STEAROYL COA DESATURASE INHIBITORS
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Page/Page column 31-32, (2010/04/30)
The present invention discloses lH-pyrido[l,2-a]pyrimidin-4(9aH)~one derivatives or IH- pyrimido[l,2-a]pyrimidin-4(9aH)~one derivatives for use as inhibitors of stearoyl-CoA desaturase having the structure of Formula I: Formula I. The compounds are useful
Structure-activity relationships of phenylpropanoids as antifeedants for the pine weevil Hylobius abietis
Bohman,Nordlander,Nordenhem,Sunnerheim,Borg-Karlson,Unelius
, p. 339 - 352 (2008/09/18)
Ethyl cinnamate has been isolated from the bark of Pinus contorta in the search for antifeedants for the pine weevil, Hylobius abietis. Based on this lead compound, a number of structurally related compounds were synthesized and tested. The usability of the Topliss scheme, a flow diagram previously used in numerous structure-activity relationship (SAR) studies, was evaluated in an attempt to find the most potent antifeedants. The scheme was initially followed stepwise; subsequently, all compounds found in the scheme were compared. In total, 51 phenylpropanoids were tested and analyzed for SARs by using arguments from the field of medicinal chemistry (rational drug design). Individual Hansch parameters based on hydrophobicity, steric, and electronic properties were examined. The effects of position and numbers of substituents on the aromatic ring, the effects of conjugation in the molecules, and the effects of the properties of the parent alcohol part of the esters were also evaluated. It proved difficult to find strong SARs derived from single physicochemical descriptors, but our study led to numerous new, potent, phenylpropanoid antifeedants for the pine weevil. Among the most potent were methyl 3-phenylpropanoates monosubstituted with chloro, fluoro, or methyl groups and the 3,4-dichlorinated methyl 3-phenylpropanoate.
Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach
Sunnerheim, Kerstin,Nordqvist, Anneli,Nordlander, Goeran,Borg-Karlson, Anna-Karin,Unelius, C. Rickard,Bohman, Bjoern,Nordenhem, Henrik,Hellqvist, Claes,Karlen, Anders
, p. 9365 - 9372 (2008/03/17)
Antifeedant activity of mainly phenylpropanoic, cinnamic, and benzoic acids esters was tested on the pine weevil, Hylobius abietis (L.). Of 105 compounds screened for activity, 9 phenylpropanoates, 3 cinnamates, and 4 benzoates were found to be highly active antifeedants. To understand the structure-activity relationships of these compounds, a multivariate analysis study was performed. A number of molecular and substituent descriptors were calculated and correlated to results from two-choice feeding tests with H. abietis. Three local models were developed that had good internal predictive ability. External test sets showed moderate predictivity. In general, low polarity, small size, and high lipophilicity were characteristics for compounds having good antifeedant activity.
Synthesis and Antileukemic Activity of Bismethyl>-Substituted Pyrroloisoquinolines, Pyrroloquinolines, Pyrroloisobenzazepines, and Pyrrolobenzazepines
Anderson, Wayne K.,Heider, Arvela R.,Raju, Natarajan,Yucht, Jeffery A.
, p. 2097 - 2102 (2007/10/02)
A series of bismethyl>-substituted pyrrole-fused tricyclic heterocycles were synthesized by using 1,3-dipolar cycloaddition reactions with a trifluoromethanesulfonate salt of an appropriate Resissert compound or with a mesoionic oxazolone intermediate.All of the bis(carbamates) were active in vivo against P388 lymphocytic leukemia with 5,6-dihydro-8-methoxy-1,2-bis(hydroxymethyl)pyrroloisoquinoline bis (3c) showing the highest level of activity.
