695-98-7Relevant articles and documents
Use of α,ω-Dichloroketimine Building Blocks for the Construction of 1-Azabicyclo[31.0]hexanes, Piperidines, Pyridines, Pyrroles, and Tetrahydroindoles
Piens, Nicola,Aelterman, Wim,D'Hooghe, Matthias,De Kimpe, Norbert
, p. 207 - 213 (2017/01/25)
A variety of different N-[2-chloro-4-(chloromethyl)pent-4-enylidene]amines and N-(2,6-dichlorohex-4-enylidene)amines was prepared for the first time, and their reactivity as eligible building blocks for the synthesis of biologically relevant nitrogen-containing heterocyclic compounds was studied. In this way, a convenient entry into functionalized 1-azabicyclo[3.1.0]hexanes, piperidines, pyridines, pyrroles, and tetrahydroindoles was developed, pointing to the broad synthetic flexibility of these dichlorinated imine substrates.
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.
Convenient procedure for the α-methylation of simple pyridines
Broering, Martin,Kleeberg, Christian
scheme or table, p. 3672 - 3682 (2009/04/03)
A convenient and straightforward laboratory procedure is presented for a highly selective mono-α-methylation of pyridines without reactive functional groups. The methylating agent is probably carbon monoxide/dihydrogen generated in situ from a high-boiling alcohol on a metal surface. The reaction is catalyzed by a Raney nickel catalyst at ambient pressure, which renders the protocol practicable in standard organic laboratories. The intrinsically high reaction temperature and long reaction times restrict the application to pyridine derivatives with less reactive substituents. The outcome of the reaction can be rationalized by the assumption of a simple heterogeneous mechanism. Copyright Taylor & Francis Group, LLC.