90682-31-8Relevant academic research and scientific papers
ECO-FRIENDLY MATERIALS AND METHODS FOR RENEWABLE AND SUSTAINABLE APPLICATIONS IN MATERIAL CHEMISTRY
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Page/Page column 42, (2017/09/27)
The invention relates to novel hydrazide-based templates, methods of making the same, and methods of using the hydrazide-based templates as molecular scaffolds for asymmetric light driven transformations, light driven material synthesis, and biological applications. Furthermore, the present invention relates to photoinitiators, monomers, and polymers derived from biomass, together with methods and methods of using the same.
Development of a scalable process for CI-1034, an endothelin antagonist
Jacks, Thomas E.,Belmont, Daniel T.,Briggs, Christopher A.,Horne, Nicole M.,Kanter, Gerald D.,Karrick, Greg L.,Krikke, James J.,McCabe, Richard J.,Mustakis, Jason G.,Nanninga, Thomas N.,Risedorph, Guy S.,Seamans, Ronald E.,Skeean, Richard,Winkle, Derick D.,Zennie, Thomas M.
, p. 201 - 212 (2013/09/04)
A concise, convergent multikilogram synthesis of CI-1034 (1), a potent endothelin receptor antagonist, is described. A 15-step preparation from commercially available o-vanillin and benzenesulfonyl chloride employs a remarkably robust Suzuki coupling between a boronic acid and an aromatic sulfonate ester as the key synthetic step. A scalable route capable of producing multikilogram quantities of CI-1034 with no chromatographic steps is described in this contribution. Improvements to the process included using a 4-fluorobenzenesulfonate ester as a suitable substitute for the triflate group in the Suzuki reaction and the use of MgCl2 as a substitute for TiCl4 in a Dieckmann condensation to provide the benzothiazine dioxide core.
Synthesis of 1H-2-benzopyran-5,8-dione derivatives from 2-(1-hydroxyalkyl)-1,4-benzoquinones and enamines
Kobayashi, Kazuhiro,Nomura, Kosaku,Ogata, Toshikazu,Tanmatsu, Miyuki,Morikawa, Osamu,Konishi, Hisatoshi
, p. 673 - 676 (2007/10/03)
An efficient synthesis of the title benzopyranodione derivatives based on a Michael addition/cyclization sequence between 2-(1-hydroxyalkyl)-1,4-benzoquinones and enamines (or an imine) is described.
Isolation, Synthesis, Structure-Activity Relationships of Bioactive Benzoquinones from Miconia lepidota from the Suriname Rainforest
Gunatilaka, A. A. Leslie,Berger, John M.,Evans, Randy,Miller, James S.,Wisse, Jan H.,Neddermann, Kim M.,Bursuker, Isia,Kingston, David G. I.
, p. 2 - 5 (2007/10/03)
Bioactivity-directed fractionation of an EtOAc extract from the leaves of Miconia lepidota afforded the two benzoquinones 2-methoxy-6-heptyl-1,4-benzoquinone (1) and 2-methoxy-6-pentyl-1,4-benzoquinone (primin) (2). This is the first reported isolation of
Synthesis of Side-Chain-Modified Analogues of the Allergen Primin
Koenig, Wilfried A.,Faasch, Holger,Heitsch, Holger,Colberg, Cornelia,Hausen, Bjoern M.
, p. 387 - 393 (2007/10/02)
Benzoquinones such as primin (2-methoxy-6-pentyl-1,4-benzoquinone) from Primula obconica HANCE (Primulaceae) are known to be strong sensitizers and thus the source of severe allergic contact dermatitis (cell-mediated type of allergy).In order to determine
Tobacco smoke chemistry. 2. Alkyl and alkenyl substituted guaiacols found in cigarette smoke condensate.
Arnarp,Bielawski,Dahlin,Dahlman,Enzell,Pettersson
, p. 44 - 50 (2007/10/02)
A series of alkyl and alkenyl substituted guaiacols, which comprise a group of biologically and organoleptically active compounds, have been synthesized. Mass spectra and GC retention times for these have been recorded and compared with those obtained for constituents of a weakly acidic fraction of smoke condensate derived from American blend type cigarettes. On the basis of these results, 25 guaiacols have been identified, 18 of which have not been detected in tobacco smoke condensate previously.
Metalation of Phenols. Synthesis of Benzoquinones by the Oxidative Degradation Approach
Saa, Jose M.,Llobera, Antonia,Garcia-Raso, Angel,Costa, Antonio,Deya, Pedro M.
, p. 4263 - 4273 (2007/10/02)
In a effort to explore the potential of so-called oxidative degradation approach for the synthesis of quinones, we have investigated the direct metalation of a number of simple phenols such as o- and p-hydroxybenzyl alcohols, benzyl methyl ethers and N,N-dimethylbenzylamines.Apparently, only those phenolic substrates having available both a coordinating group for chelation and an electron-withdrawing group in a 1,3-relationship are efficiently lithiated, by the action of n-BuLi, in a regioselective manner.Those positions on the aromatic nucleus just flanked by a coordinating, or an acid-base, group could be metalated by action of the t-BuLi/THP system, in favorable cases.
