1380198-06-0Relevant academic research and scientific papers
Ruthenium-catalyzed oxidative coupling of primary amines with internal alkynes through C-H bond activation: Scope and mechanistic studies
Ruiz, Sara,Villuendas, Pedro,Ortu?o, Manuel A.,Lled?s, Agustí,Urriolabeitia, Esteban P.
supporting information, p. 8626 - 8636 (2015/06/02)
The oxidative coupling of primary amines with internal alkynes catalyzed by Ru complexes is presented as a general atom-economy methodology with a broad scope of applications in the synthesis of N-heterocycles. Reactions proceed through regioselective C-H bond activation in 15 minutes under microwave irradiation or in 24 hours with conventional heating. The synthesis of 2,3,5-substituted pyridines, benzo[h]isoquinolines, benzo[g]isoquinolines, 8,9-dihydro-benzo[de]quinoline, 5,6,7,8-tetrahydroisoquinolines, pyrido[3,4g]isoquinolines, and pyrido[4,3g]isoquinolines is achievable depending on the starting primary amine used. DFT calculations on a benzylamine substrate support a reaction mechanism that consists of acetate-assisted C-H bond activation, migratory-insertion, and C-N bond formation steps that involve 28-30 kcalmol-1. The computational study is extended to additional substrates, namely, 1-naphthylmethyl-, 2-methylallyl-, and 2-thiophenemethylamines.
Ruthenium-catalyzed highly regioselective cyclization of ketoximes with alkynes by C-H bond activation: A practical route to synthesize substituted isoquinolines
Chinnagolla, Ravi Kiran,Pimparkar, Sandeep,Jeganmohan, Masilamani
supporting information; experimental part, p. 3032 - 3035 (2012/08/07)
Aromatic and heteroaromatic ketoximes underwent cyclization with alkynes in the presence of a catalytic amount of [{RuCl2(p-cymene)} 2] and NaOAc to give isoquinoline derivatives in good to excellent yields in a highly regioselective
