91133-05-0Relevant articles and documents
Catalytic asymmetric formal [3+2] cycloaddition of isatogens with azlactones to construct indolin-3-one derivatives
Xie, Lihua,Li, Yi,Dong, Shunxi,Feng, Xiaoming,Liu, Xiaohua
supporting information, p. 239 - 242 (2021/01/14)
The chiral amide-guanidine-catalyzed asymmetric formal [3+2] cycloaddition of isatogens with azlactones is presented. This strategy provided a facile and feasible route to chiral indolin-3-one derivatives bearing two contiguous tetrasubstituted stereocent
Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source
Guan, Xinyu,Zhu, Haoran,Zhao, Yingwei,Driver, Tom G.
supporting information, p. 57 - 60 (2019/12/11)
A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.
Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals
Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Ly, Michelle,White, Frankie D.,Alabugin, Igor V.
, p. 4265 - 4278 (2017/04/27)
Selective addition of radicals to isonitriles can be harnessed for initiating reaction cascades designed to overcome the stereoelectronic restrictions on homoallylic ring expansion in alkyne reactions and to develop a new general route for the preparation of N-heteroaromatics. This method utilizes alkenes as synthetic equivalents of alkynes by coupling homoallylic ring expansion to yield the formal "6-endo" products with aromatization via stereoelectronically assisted C-C bond scission. Computational analysis of the homoallyic expansion potential energy surface reveals that the indirect 5-exo/3-exo/retro-3-exo path is faster than the direct 6-endo-trig closure, revealing the general exo-preference for the cyclization processes.
Double C-H amination by consecutive SET oxidations
Evoniuk, Christopher J.,Hill, Sean P.,Hanson, Kenneth,Alabugin, Igor V.
supporting information, p. 7138 - 7141 (2016/06/09)
A new method for intramolecular C-H oxidative amination is based on a FeCl3-mediated oxidative reaction of anilines with activated sp3 C-H bonds. The amino group plays multiple roles in the reaction cascade: (1) as the activating group in single-electron-transfer (SET) oxidation process, (2) as a directing group in benzylic/allylic C-H activation at a remote position, and (3) internal nucleophile trapping reactive intermediates formed from the C-H activation steps. These multielectron oxidation reactions proceed with catalytic amounts of Fe(iii) and inexpensive reagents.
Palladium-Catalyzed Formation of N-Heteroarenes from Nitroarenes using Molybdenum Hexacarbonyl as the Source of Carbon Monoxide
Zhou, Fei,Wang, Duo-Sheng,Driver, Tom G.
supporting information, p. 3463 - 3468 (2016/01/25)
The development of a method that employs a two-chamber reaction vessel and uses molybdenum hexacarbonyl [Mo(CO)6] as the carbon monoxide (CO) source for the palladium-catalyzed transformation of nitroarenes into indoles or imidazoles is reported.
Coupling cyclizations with fragmentations for the preparation of heteroaromatics: Quinolines from o-alkenyl arylisocyanides and boronic acids
Evoniuk, Christopher J.,Ly, Michelle,Alabugin, Igor V.
supporting information, p. 12831 - 12834 (2015/08/06)
Stereoelectronic restrictions on homoallylic ring expansion in alkyne cascades can be overcome by using alkenes as synthetic equivalents of alkynes in reaction cascades that are terminated by C-C bond fragmentation. Implementation of this approach using Mn(iii)-mediated reaction of o-alkenyl isocyanides and boronic acids leads to efficient synthesis of substituted quinolines.
Ionic diamine rhodium complex catalyzed reductive N-heterocyclization of 2-nitrovinylarenes
Okuro, Kazumi,Gurnham, Joanna,Alper, Howard
experimental part, p. 4715 - 4720 (2011/07/08)
Ionic diamine rhodium complex (1) catalyzes the reductive N-cyclization of 2-vinylnitroarenes using carbon monoxide as a reducing agent to afford functionalized indoles. The catalytic system allows direct access to indoles with ester and ketone groups at the 2- or 3-position, in good yields.
A versatile protocol for the quantitative and smooth conversion of phosphane oxides into synthetically useful pyrazolylphosphonium salts
Feldmann, Kai-Oliver,Schulz, Stephen,Klotter, Felix,Weigand, Jan J.
experimental part, p. 1805 - 1812 (2012/04/04)
A convenient protocol for the smooth conversion of the resistant P-O bond in phosphane oxides into a reactive P-N bond of synthetically useful pyrazolylphosphonium salts is described. A highly charged, oxophilic, phosphorus-centered trication is employed and the reactions are conducted at room temperature with quantitative yields. The resulting pyrazolylphosphonium cations are valuable synthetic intermediates and are used for the synthesis of a variety of organophosphorus compounds. This represents a new approach towards the transformation of the rather inert phosphoryl group under very mild reaction and workup conditions and aims towards alternatives to existing reduction methods for phosphane oxide functionalization.
Structural development of liver X receptor (LXR) antagonists derived from thalidomide-related glucosidase inhibitors
Noguchi-Yachide, Tomomi,Miyachi, Hiroyuki,Aoyama, Hiroshi,Aoyama, Atsushi,Makishima, Makoto,Hashimoto, Yuichi
, p. 1750 - 1754 (2008/09/17)
Following our previous discovery of LXR antagonistic activity of 2′-substituted phenylphthalimides derived from thalidomide-related glucosidase inhibitors, structure-activity studies and further structural development led to 5-chloro-N-2′-n-pentylphenyl-1,3-dithiophthalimide (5CPPSS-50), with IC50 values of about 10 and 13 μM for LXRα and LXR β, respectively.
Amides as precursors of imidoyl radicals in cyclisation reactions
Bowman, W. Russell,Fletcher, Anthony J.,Pedersen, Jan M.,Lovell, Peter J.,Elsegood, Mark R.J.,Hernández López, Elena,McKee, Vickie,Potts, Graeme B.S.
, p. 191 - 203 (2007/10/03)
Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals for cyclisation reactions. Imidoyl radicals have been cyclised onto alkenes to yield 2,3-substituted-indoles and -quinolines and also onto pyrroles and indoles to give bi- and tricyclic heteroarenes.
