289507-36-4Relevant academic research and scientific papers
Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
Steeds, Hannah G.,Knowles, Jonathan P.,Yu, Wai L.,Richardson, Jeffery,Cooper, Katie G.,Booker-Milburn, Kevin I.
supporting information, p. 14330 - 14334 (2020/10/12)
A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.
Regioselective synthesis of 2,4-differentially arylated pyrroles and its application to the synthesis of lamellarins
Fukuda, Tsutomu,Anzai, Mizuho,Iwao, Masatomo
, p. 593 - 612 (2017/04/10)
An efficient method for the synthesis of 2,4-differentially arylated pyrroles has been developed via stepwise palladium-catalyzed Suzuki-Miyaura coupling of N-benzenesulfonyl-4-bromo-2-iodopyrrole with different arylboronic acids. This method has been applied to the new synthesis of the marine natural products lamellarins.
CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines
Kiruthika, Selvarangam E.,Perumal, Paramasivan Thirumalai
supporting information, p. 484 - 487 (2014/04/03)
A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.
Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids
Kapadia, Nirav,Harding, Wayne
supporting information, p. 8914 - 8920 (2013/09/23)
Oxa-Pictet-Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g]chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps.
DIHYDROIMIDAZOISOQUINOLINE DERIVATIVES USEFUL AS PDE10 INHIBITORS
-
Page/Page column 34-35, (2011/02/24)
The present invention relates to dihydroimidazoisoquinolines and derivatives thereof, the use of the compounds as phosphodiesterase 10 (PDE10) inhibitors for the treatment of PDE10-modulated disorders, to pharmaceutical compositions comprising the compounds.
One-pot synthesis of aminoenone via direct reaction of the chloroalkyl enone with NaN3: Rapid access to polycyclic alkaloids
Zhao, Yu-Ming,Gu, Peiming,Tu, Yong-Qiang,Zhang, Hai-Jun,Zhang, Qing-Wei,Fan, Chun-An
supporting information; experimental part, p. 5289 - 5295 (2010/10/19)
(Figure presented) A new one-pot procedure for the preparation of aminoenone from chloroalkyl enone and sodium azide was demonstrated. The structure of the presumed triazoline intermediate in this process was confirmed by X-ray analysis for the first time. As the application of this methodology, the synthesis of polycyclic alkaloid hexahydroapoerysopine (1a) was achieved through an efficient synthetic route.
The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine alkaloids lamellarin G trimethyl ether and ningalin B
Gupton, John T.,Giglio, Benjamin C.,Eaton, James E.,Rieck, Elizabeth A.,Smith, Kristin L.,Keough, Matthew J.,Barelli, Peter J.,Firich, Lauren T.,Hempel, Jonathan E.,Smith, Timothy M.,Kanters, Rene P.F.
experimental part, p. 4283 - 4292 (2009/10/17)
Studies directed at the synthesis of lamellarin G trimethyl ether and ningalin B via vinylogous iminium salt derivatives are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 1,2,3,4-tetrasubstituted pyrrole fr
A Modular Synthesis of the Lamellarins: Total Synthesis of Lamellarin G Trimethyl Ether
Handy, Scott T.,Zhang, Yanan,Bregman, Howard
, p. 2362 - 2366 (2007/10/03)
A modular synthesis of the lamellarin family of natural products has been developed that is based on the application of three iterative halogenation/cross-coupling reaction sequences. The ability to halogenate the pyrrole core in a regioselective fashion, even in the presence of highly electron-rich aryl substituents, has been established. The compatibility of Suzuki coupling conditions with free alcohols and phenols in the boronic acids has been employed to reduce the number of protection/deprotection steps. Indeed, the presence of a free phenol on boronic acid 3 has been determined to be critical for the successful final coupling in route to lamellarin G trimethyl ether, since protected versions fail to undergo coupling.
A NEW SYNTHESIS OF 2-AMINO-6,7-DIHYDROXY-TETRAHYDRONAPHTHALENE (ADTN) VIA FUNCTIONALIZED ARYL-LITHIUM REAGENTS AND METHYL 2-TRIMETHYLSILYLACRYLATE - A NEW ANNULATION SEQUENCE
Narula, Anubhav P.S.,Schuster, David I.
, p. 3707 - 3710 (2007/10/02)
A new high yield synthesis of a potent dopamine agonist, 2-amino-6,7-dihydroxy-tetrahydronaphthalene, is described utilizing a new annulation sequence.
