6837-27-0Relevant academic research and scientific papers
Transition-Metal-Free Deconstructive Lactamization of Piperidines
Romero-Iba?ez, Julio,Cruz-Gregorio, Silvano,Sandoval-Lira, Jacinto,Hernández-Pérez, Julio M.,Quintero, Leticia,Sartillo-Piscil, Fernando
supporting information, p. 8867 - 8871 (2019/05/28)
One of the major challenges in organic synthesis is the activation or deconstructive functionalization of unreactive C(sp3)–C(sp3) bonds, which requires using transition or precious metal catalysts. We present here an alternative: the deconstructive lactamization of piperidines without using transition metal catalysts. To this end, we use 3-alkoxyamino-2-piperidones, which were prepared from piperidines through a dual C(sp3)–H oxidation, as transitory intermediates. Experimental and theoretical studies confirm that this unprecedented lactamization occurs in a tandem manner involving an oxidative deamination of 3-alkoxyamino-2-piperidones to 3-keto-2-piperidones, followed by a regioselective Baeyer–Villiger oxidation to give N-carboxyanhydride intermediates, which finally undergo a spontaneous and concerted decarboxylative intramolecular translactamization.
Carbazole-containing amides and ureas: Discovery of cryptochrome modulators as antihyperglycemic agents
Humphries, Paul S.,Bersot, Ross,Kincaid, John,Mabery, Eric,McCluskie, Kerryn,Park, Timothy,Renner, Travis,Riegler, Erin,Steinfeld, Tod,Turtle, Eric D.,Wei, Zhi-Liang,Willis, Erik
, p. 293 - 297 (2018/01/04)
A series of novel carbazole-containing amides and ureas were synthesized. A structure–activity relationship study of these compounds led to the identification of potent cryptochrome modulators. Based on the desired pharmacokinetic/pharmacodynamic parameters and the results of efficacy studies in db/db mice, compound 50 was selected for further profiling.
Cobalt-Catalyzed Cross-Coupling of α-Bromo Amides with Grignard Reagents
Barde,Guérinot,Cossy
, p. 6068 - 6071 (2017/11/28)
A cobalt-catalyzed cross-coupling between α-bromo amides and Grignard reagents is disclosed. The reaction is general and allows access to a large variety of α-aryl and β,γ-unsaturated amides. Some mechanistic investigations have been undertaken to determine the nature of the intermediate species.
Kinetic resolution of racemic pyrrolidine-2,5-diones using chiral oxazaborolidine catalysts
Barker, Mike D.,Dixon, Rachel A.,Jones, Simon,Marsh, Barrie J.
, p. 2218 - 2220 (2008/12/22)
Kinetic resolution of racemic C-3 substituted pyrrolidine-2,5-diones has been achieved for the first time using highly efficient oxazaborolidine catalysts derived from cis-1-amino-indan-2-ol. The Royal Society of Chemistry.
