351900-17-9Relevant academic research and scientific papers
Highly chemoselective, sterically sensitive NHC-catalysed amine acylation with pyridil
Maguire, Amy C.,Kumar, Vikas,Connon, Stephen J.
supporting information, p. 13526 - 13529 (2019/11/14)
A new strategy for the protection of amines has been developed involving reaction with pyridil under the influence of N-heterocyclic carbene catalysis. The methodology is capable of distinguishing between two amines characterised by small differences in steric bulk and the resulting pyridoyl amides can be cleaved without requiring either strongly acidic or basic hydrolysis.
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates
Ragnarsson, Ulf,Grehn, Leif,Maia, Hernani L.S.,Monteiro, Luis S.
, p. 97 - 101 (2007/10/03)
Synthetic and spectroscopic details relating to a set of heteroaromatic N-benzyl carboxamides and in particular the corresponding tert-butyl acylcarbamates are reported. These compounds were required to study the postulated effect of various heterocycles
Enhancing Reductive Cleavage of Aromatic Carboxamides
Ragnarsson, Ulf,Grehn, Leif,Maia, Hernani L. S.,Monteiro, Luis S.
, p. 2021 - 2022 (2007/10/03)
(matrix presented) A set of aromatic and especially heteroaromatic N-benzyl carboxamides, derived from naphthalene, pyridine, pyrazine, and quinoline, and the corresponding tert-butyl acylcarbamates have been synthesized and studied by cyclic voltammetry with respect to facilitated reduction. The latter undergo regiospecific cleavage of their C(O)-N bonds under very mild reductive conditions with formation of Boc-protected (benzyl)-amine in most cases in nearly quantitative yields. Examples of preparative cleavage by controlled potential electrolysis, activated aluminum, and NaBH4 are given.
