104375-68-0Relevant academic research and scientific papers
Gold(I)-catalyzed domino ring-opening ring-closing hydroamination of methylenecyclopropanes (MCPs) with sulfonamides: Facile preparation of pyrrolidine derivatives
Shi, Min,Liu, Le-Ping,Tang, Jie
, p. 4043 - 4046 (2006)
Reaction of methylenecyclopropanes 1 with sulfonamides produces the corresponding pyrrolidine derivatives 3 in moderate to good yields under the catalysis of Au(I) via a domino ring-opening ring-closing hydroamination process.
Palladium-catalyzed inter- and intramolecular hydroamination of styrenes coupled with alcohol oxidation using N-fluorobenzenesulfonimide as the oxidant
Xu, Tao,Qiu, Shuifa,Liu, Guosheng
experimental part, p. 46 - 49 (2011/02/17)
Palladium-catalyzed inter- and intramolecular hydroaminations of styrenes that are coupled to alcohol oxidation under oxidative condition are reported. The fluorination reagent NFSI is used as the nitrogen source as well as the oxidant. Bidental nitrogen
Gold- and silver-catalyzed tandem amination/ring expansion of cyclopropyl methanols with sulfonamides as an expedient route to pyrrolidines
Rao, Weidong,Chan, Philip Wai Hong
experimental part, p. 10486 - 10495 (2009/10/15)
An efficient synthetic route to pyrrolidines that relies on AuCl/ AgOTf-catalyzed tandem amination/ ring expansion of substituted cyclopropyl methanols with sulfonamides is reported herein. The reactions proceed rapidly at 100 °C with catalyst loadings as low as 2 mol % and produce the pyrrolidine products in yields of 30-95%. The method was shown to be applica ble to a broad range of cyclopropyl methanols, including unactivated ones, and sulfonamide substrates containing electron-withdrawing, electron-donating, and sterically-demanding substitu ents. The mechanism is suggested to involve activation of the alcohol substrate by the AuCl/AgOTf catalyst, followed by ionization of the starting material, which causes ring opening of the cyclopropane moiety and trapping by the sulfonamide nucleophile. The resultant aminated acyclic intermediate undergoes subsequent intramolecular hydroamination to give the pyrrolidine.
Bronsted acid-catalyzed intramolecular hydroamination of protected alkenylamines. Synthesis of pyrrolidines and piperidines.
Schlummer, Bjoern,Hartwig, John F
, p. 1471 - 1474 (2007/10/03)
[reaction: see text]. The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-phenylanilides also underwent cyclization to form gamma-lactams.
1-arenesulfonyl-2-aryl-pyrrolidine and pyridine derivatives
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, (2008/06/13)
1-Arenesulfonyl-2-Aryl-pyrrolidine and pyridine derivatives having activity as ligands of metabotropic glutamate receptors of the formula are disclosed.
Synthesis of Five- and Six-Membered Nitrogen Heterocycles via a Palladium(II)-Catalyzed Cyclization of Unsaturated Amides
Tamaru, Yoshinao,Hojo, Makoto,Kawamura, Shin-ichi,Yoshida, Zen-ichi
, p. 4089 - 4090 (2007/10/02)
Palladium(II)-catalyzed arylation of N-4-pentenyl-p-toluenesulfonamides 2 with ArSn(n-Bu)3 under oxidative conditions (CuCl2 in ether) provides either 2-arylpiperidines 5 or N-(chloro-5-arylpentyl)-p-toluenesulfonamides 6 depending on the kind of arylatin
