7661-30-5Relevant articles and documents
Heterogeneous CuII-catalysed solvent-controlled selective N-arylation of cyclic amides and amines with bromo-iodoarenes
Kundu, Debasish,Bhadra, Sukalyan,Mukherjee, Nirmalya,Sreedhar, Bojja,Ranu, Brindaban C.
, p. 15759 - 15768 (2013/11/19)
A selective N-arylation of cyclic amides and amines in DMF and water, respectively, catalysed by CuII/Al2O3 has been achieved. This protocol has been employed for the synthesis of a library of arenes bearing a cyclic amide and an amine moiety at two ends, including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed electron paramagnetic resonance (EPR) spectroscopy, X-ray photoelectron spectroscopy (XPS), UV diffuse reflectance spectroscopy (DRS) and inductively coupled plasma-mass spectrometry (ICP-MS) studies of the catalyst at different stages of the reaction. The CuII/Al2O 3 catalyst was recovered and recycled for subsequent reactions. One over the other: A selective N-arylation of cyclic amides and amines in DMF and water, respectively, catalyzed by CuII/Al2O3 has been achieved (see scheme). This protocol has been employed for the synthesis of a library of arenes bearing cyclic amide and amine moieties at two ends including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed spectroscopic studies (FG=functional group). Copyright
Reformatsky reactions with N-arylpyrrolidine-2-thiones: Synthesis of tricyclic analogues of quinolone antibacterial agents
Michael, Joseph P,De Koning, Charles B,Hosken, Gladys D,Stanbury, Trevor V
, p. 9635 - 9648 (2007/10/03)
A convenient synthesis of 5-oxo-1,2,3,5-tetrahydropyrrolo[1,2-α]quinoline-4-carboxylic acids, tricylic analogues of the quinolone antibiotics, is described. Key steps in the route are a novel zinc-mediated Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thione 18, and cyclisation of the resulting diethyl pyrrolidinylidenemalonate intermediates 19 in polyphosphoric acid. The products proved to be devoid of biological activity.