56490-94-9Relevant articles and documents
Electrochemical Aziridination of Internal Alkenes with Primary Amines
Bartolomeu, Aloisio de A.,Dyga, Marco,Goo?en, Lukas J.,Laudadio, Gabriele,No?l, Timothy,O?eka, Maksim,de Bruin, Bas,de Oliveira, Kleber T.,van Leest, Nicolaas P.
, p. 255 - 266 (2021/01/19)
An electrochemical approach to prepare aziridines via an oxidative coupling between alkenes and primary alkyl amines was realized. The reaction is carried out in an electrochemical flow reactor, leading to short reaction/residence times (5 min), high yields, and broad scope. At the cathode, hydrogen is generated, which can be used in a second reactor to reduce the aziridine yielding the corresponding hydroaminated product.Aziridines are useful synthetic building blocks, widely employed for the preparation of various nitrogen-containing derivatives. As the current methods require the use of prefunctionalized amines, the development of a synthetic strategy toward aziridines that can establish the union of alkenes and amines would be of great synthetic value. Herein, we report an electrochemical approach, which realizes this concept via an oxidative coupling between alkenes and primary alkylamines. The reaction is carried out in an electrochemical flow reactor leading to short reaction/residence times (5 min), high yields, and broad scope. At the cathode, hydrogen is generated, which can be used in a second reactor to reduce the aziridine, yielding the corresponding hydroaminated product. Mechanistic investigations and DFT calculations revealed that the alkene is first anodically oxidized and subsequently reacted with the amine coupling partner.The central tenet in modern synthetic methodology is to develop new methods only using widely available organic building blocks. As a direct consequence, new activation strategies are required to cajole the coupling partners to react and, subsequently, forge new and useful chemical bonds. Using electrochemical activation, our methodology enables for the first time the direct coupling between olefins and amines to yield aziridines. Aziridines display interesting pharmacological activity and serve as valuable synthetic intermediates to prepare diverse nitrogen-containing derivatives. Interestingly, the sole byproduct generated in this process is hydrogen, which can be subsequently used to reduce the aziridine into the corresponding hydroaminated product. Hence, this electrochemical methodology can be regarded as green and sustainable from the vantage point of upgrading simple and widely available commodity chemicals.
Preparation of Substituted Tetrahydroisoquinolines by Pd(II)-Catalyzed NH2-Directed Insertion of Michael Acceptors into C-H Bonds Followed by NH2-Conjugated Addition
Mancinelli, Andrea,Alamillo, Carla,Albert, Joan,Ariza, Xavier,Etxabe, Haizea,Farràs, Jaume,Garcia, Jordi,Granell, Jaume,Quijada, F. Javier
, p. 911 - 919 (2017/04/21)
3,3-Disubstituted tetrahydroisoquinolines are prepared in one step from Michael acceptors and 2-phenylethylamines under Pd catalysis and Ag2CO3 as an oxidant. Presumably, activation of an ortho C-H bond of the aromatic ring with Pd(II) is directed by the primary amine to form a palladacycle. Insertion of the olefin, subsequent conjugated addition of the amine, and reductive elimination of Pd(0) affords the expected products. Silver carbonate is not necessary when 2-phenylethylamines are converted previously to N-benzoyloxy-2-phenylethylamines.
Discovery of olodaterol, a novel inhaled β2-adrenoceptor agonist with a 24 h bronchodilatory efficacy
Bouyssou, Thierry,Hoenke, Christoph,Rudolf, Klaus,Lustenberger, Philipp,Pestel, Sabine,Sieger, Peter,Lotz, Ralf,Heine, Claudia,Büttner, Frank H.,Schnapp, Andreas,Konetzki, Ingo
scheme or table, p. 1410 - 1414 (2010/07/10)
Compound 4p was identified from a series of 6-hydroxy-4H-benzo[1,4]oxazin-3-ones as potent agonist of the human β2-adrenoceptor with a high β1/β2-selectivity. A complete reversal of acetylcholine-induced bronchoconstrictio
