138490-95-6Relevant articles and documents
Synthesis of 2,3,9,10-Tetraoxygenated benzo[c]phenanthridine derivatives via palladiummediated aryl-Aryl coupling reaction
Abe, Hitoshi,Kobayashi, Naoko,Kadoshima, Yutaka,Takeuchi, Yasuo,Harayama, Takashi,Horino, Yoshikazu
, p. 673 - 684 (2017/04/10)
Two 2,3,9,10-Tetraoxygenated benzo[c]phenanthridine alkaloids, 1 2, originally reported as zanthoxyline and broussonpapyrine, respectively, were synthesized using the Pd-mediated intramolecular aryl-Aryl coupling reaction as the key step.
Chemoselective zinc/HCl reduction of halogenated β-nitrostyrenes: Synthesis of halogenated dopamine analogues
Maresh, Justin J.,Ralko, Arthur A.,Speltz, Tom E.,Burke, James L.,Murphy, Casey M.,Gaskell, Zachary,Girel, Joann K.,Terranova, Erin,Richtscheidt, Conrad,Krzeszowiec, Mark
supporting information, p. 2891 - 2894 (2015/02/02)
A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 °C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.
Enantioselective synthesis of multisubstituted biaryl skeleton by chiral phosphoric acid catalyzed desymmetrization/kinetic resolution sequence
Mori, Keiji,Ichikawa, Yuki,Kobayashi, Manato,Shibata, Yukihiro,Yamanaka, Masahiro,Akiyama, Takahiko
supporting information, p. 3964 - 3970 (2013/04/24)
Described herein is the enantioselective synthesis of multisubstituted biaryl derivatives by chiral phosphoric acid catalyzed asymmetric bromination. Two asymmetric reactions (desymmetrization and kinetic resolution) proceeded successively to afford chiral biaryls in excellent enantioselectivities (up to 99% ee). Both experimental and computational studies suggested that this excellent selectivity could be achieved via a highly organized hydrogen bond network among a substrate, a catalyst (chiral phosphoric acid), and a brominating reagent (N-bromophthalimide).
Electronic control of product distribution in the [5+5]-coupling of ortho-alkynylbenzaldehyde derivatives and γ,δ-unsaturated carbene complexes
Camacho-Davila, Alejandro,Gamage, Lalith S.R.,Wang, Zhipeng,Herndon, James W.
supporting information; experimental part, p. 4954 - 4960 (2010/08/19)
The coupling of highly oxygenated ortho-alkynylbenzaldehyde derivatives with γ,δ-carbene complexes was evaluated systematically. In all of the electron-rich systems investigated the exclusive product of the reaction is the dihydrophenanthrene derivative.
Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions
Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Tokuda, Masao,Orito, Kazuhiko
experimental part, p. 5486 - 5495 (2009/12/06)
(Chemical Equation Presented) Methods for synthesis of a ring system characteristic of isoindolobenzazepine alkaloids were studied. Synthesis of lennoxamine and a formal synthesis of chelenine were accomplished in a short route via radical or Pd(0)-cataly
Synthesis of isohasubanan alkaloids via enantioselective ketone allylation and discovery of an unexpected rearrangement
Nielsen, Daniel K.,Nielsen, Laura L.,Jones, Spencer B.,Toll, Lawrence,Asplund, Matthew C.,Castle, Steven L.
supporting information; experimental part, p. 1187 - 1199 (2009/07/25)
A synthesis of the hasubanan alkaloids hasubanonine, runanine, and aknadinine via a unified route was attempted. Construction of key phenanthrene intermediates by a Suzuki coupling-Wittig olefination-ring-closing metathesis sequence allowed a convergent a
Comparison of iodination of methoxylated benzaldehydes and related compounds using iodine/silver nitrate and iodine/periodic acid
Hathaway, Bruce A.,White, Kristen L.,McGill, Mark E.
, p. 3855 - 3860 (2008/02/10)
Iodination of the three methoxybenzaldehydes, four dimethoxybenzaldehydes, vanillin, and piperonal by two methods were compared. Iodine and periodic acid gave better yields for iodination for the methoxybenzaldehydes, whereas iodine and silver nitrate generally gave better yields for the rest of the compounds. Copyright Taylor & Francis Group, LLC.
Total synthesis of (±)-hasubanonine
Jones, Spencer B.,He, Liwen,Castle, Steven L.
, p. 3757 - 3760 (2007/10/03)
Total synthesis of the alkaloid (±)-hasubanonine is described. A key feature of the route is generation of a phenanthrene intermediate via a Suzuki coupling-Wittig olefination-ring-closing metathesis sequence. Conversion of the phenanthrene into the targe
Asymmetric synthesis of (R)- and (S)-2-trifluoromethylepinephrine
Dong, Lun-Cong,Crowe, Michael,West, Jonathan,Ammann, Jeffrey R.
, p. 2731 - 2733 (2007/10/03)
An asymmetric synthesis of (R)- and (S)-2-trifluoromethylepinephrine (1R and 1S) is presented. Trifluoromethylation involves nucleophilic aromatic substitution of halobenzene 4 most likely via a copper mediated CF3 anion equivalent generated in
Novel trifluoromethylepinephrine compounds and methods of making and using thereof
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Page 9-10, (2008/06/13)
Disclosed herein are trifluoromethylepinephrine compounds having the following structural formula (I) wherein R1-R5 are each independently selected from the group consisting of H, alkyl, alkoxyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, acyl, thioacyl, sulfonyl mercapto, alkylthio, carboxy, amino, alkylamino dialkylamino, carbamoyl, arylthio, and heteroarylthio; wherein X, Y, and Z are each independently selected from the group consisting of H or trifluoromethyl with the proviso that at least one of which is trifluoromethyl. Also disclosed are pharmaceutical compositions comprising the trifluoromethylepinephrine compounds and methods of making and using thereof. Novel trifluoroepinephrine intermediates are also disclosed.
