52744-71-5Relevant academic research and scientific papers
Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation
Del Vecchio, Antonio,Talbot, Alex,Caillé, Fabien,Chevalier, Arnaud,Sallustrau, Antoine,Loreau, Olivier,Destro, Gianluca,Taran, Frédéric,Audisio, Davide
supporting information, p. 11677 - 11680 (2020/10/19)
A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.
Borane-Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction-Induced Electrocyclization
Maier, Alexander F. G.,Tussing, Sebastian,Zhu, Hui,Wicker, Garrit,Tzvetkova, Pavleta,Fl?rke, Ulrich,Daniliuc, Constantin G.,Grimme, Stefan,Paradies, Jan
supporting information, p. 16287 - 16291 (2018/10/15)
The borane-catalyzed synthesis of quinoline derivatives bearing tetrasubstituted stereocenters from vinyl anilines has been developed. Mechanistic studies and quantum-mechanical investigations support the hydride abstraction/electrocyclization/hydride add
Intramolecular addition of triarylmethanes to alkynes promoted by KOtBu/DMF: A synthetic approach to indene derivatives
Chen, Yan-Yan,Chen, Zhen-Yu,Zhang, Niu-Niu,Chen, Jia-Hua,Zhang, Xue-Jing,Yan, Ming
, p. 599 - 606 (2016/02/19)
A method for the intramolecular addition of triarylmethanes to alkynes has been developed. The reaction was efficiently promoted by KOtBu/DMF without any transition-metal catalyst. A variety of indene derivatives were prepared in moderate to good yields. A cascade cyclization of 2-alkyl-substituted substrates at elevated reaction temperature gave bicyclic indene derivatives. The reaction is proposed to proceed through the generation of a triphenylmethyl radical. Indene derivatives were prepared by the intramolecular addition of triarylmethanes to alkynes promoted by KOtBu/DMF. A cascade cyclization of 2-alkyl-substituted substrates at elevated reaction temperature gave bicyclic indene derivatives. A free-radical reaction mechanism is proposed.
Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines
Huang, Ya-Nan,Li, Yin-Long,Li, Jian,Deng, Jun
, p. 4645 - 4653 (2016/07/06)
A novel rapid synthesis of quinolines from 2-alkenylanilines has been described; the reaction involves an unexpected DMAP-catalyzed cyclization of 2-alkenylanilines with di-tert-butyl dicarbonate (Boc2O, 2.0 equiv), and a series of tert-butyl quinolin-2-yl carbonate with various functional groups have been synthesized in good yields under mild conditions. Furthermore, the tert-butyl quinolin-2-yl carbonate can be easily converted into corresponding quinolinones and 2-(pseudo)haloquinolines.
An Efficient Synthesis of 2,4-Disubstituted Quinolines by Electrophile-Mediated Cyclization Reactions of 2-Isocyanostyrene Derivatives
Kobayashi, Kazuhiro,Takagoshi, Kenichi,Kondo, Shizuka,Morikawa, Osamu,Konishi, Hisatoshi
, p. 553 - 559 (2007/10/03)
A novel quinoline synthesis starting with 2-isocyanostyrene derivatives is described. The treatment of 2-isocyanostyrene derivatives with aldehydes (or acetone) in the presence of a catalytic amount of diethyl ether-boron trifluoride afforded quinoline derivatives carrying a 1-hydroxyalkyl substituent at the 2-position. The use of acetaldehyde diethyl acetal or phenyloxirane as an electrophile under the same conditions gave the corresponding quinoline derivatives, carrying the 1-ethoxyethyl or 2-hydroxy-2-phenylethyl substituent at the 2-position, respectively. 2-Isocyanostyrene derivatives reacted with N,N-dimethyliminium salts without any catalyst to give 2-(1-dimethylaminoalkyl)quinolines.
Novel approach to isoindolo[2,1-a]quinolines
Pigeon, Pascal,Decroix, Bernard
, p. 2507 - 2516 (2007/10/03)
An N-acyliminium ion approach towards the synthesis of isoindolo [2,1- a]quinolines by an intramolecular process is described.
The Triazene Moiety as a Protecting Group for Aromatic Amines
Gross, Margaret L.,Blank, David H.,Welch, Willard M.
, p. 2104 - 2109 (2007/10/02)
Reaction of (2-), (3-), and (4-bromophenyl)-3,3-(1,4-butanediyl)triazenes (derived from the corresponding 2-, 3-, and 4-bromoanilines) with sec- or tert-butyllithiums gave the corresponding (triazenylaryl)lithiums; these intermediates reacted with a variety of electrophiles to give substituted aryl triazenes.These products could be converted to substituted anilines by reduction or to novel substituted aromatics by a modified Sandmeyer reaction.
