36048-77-8Relevant articles and documents
Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides
Moon, Yonghoon,Lee, Wooseok,Hong, Sungwoo
supporting information, p. 12420 - 12429 (2020/07/24)
By utilizing an underexplored reactivity mode of N-aminopyridinium ylides, we developed the visible-light-induced ortho-selective aminopyridylation of alkenes via radical-mediated 1,3-dipolar cycloaddition. The photocatalyzed single-electron oxidation of N-aminopyridinium ylides generates the corresponding radical cations that enable previously inaccessible 1,3-cycloaddition with a broader range of alkene substrates. The resulting cycloaddition adducts rapidly undergo subsequent homolytic cleavage of the N-N bond, conferring a substantial thermodynamic driving force to yield various β-aminoethylpyridines. Remarkably, amino and pyridyl groups can be installed into both activated and unactivated alkenes with modular control of ortho-selectivity and 1,2-syn-diastereoselectivity under metal-free and mild conditions. Combined experimental and computational studies are conducted to clarify the detailed reaction mechanism and the origins of site selectivity and diastereoselectivity.
Highly regioselective synthesis of 2,4,5-(hetero)aryl substituted oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal alkynes
Chatzopoulou, Elli,Davies, Paul W.
supporting information, p. 8617 - 8619 (2013/09/23)
A robust N-nucleophilic 1,3-N,O-dipole equivalent reacts with unsymmetrical internal alkynes under gold catalysis. Conjugation from a remote nitrogen lone pair enables and controls this convergent and highly regioselective process.
Synthesis of N-[[(substituted-phenyl)carbonyl]amino]-1,2,3,6-tetrahydropyridines with analgesic and hyperglycemic activity
Yeung,Corleto,Knaus
, p. 720 - 723 (2007/10/02)
A group of N-[(phenylcarbonyl)amino]-1,2,3,6-tetrahydropyridines, 5, were synthesized to determine the effect that changes in aromatic substitution on the phenyl ring have on analgesic, hyperglycemic, and antiinflammatory activities. All of the N-[(phenyl