221374-82-9Relevant academic research and scientific papers
Secondary Products from Intramolecular Cycloadditions of Azidoalkyl Enol Ethers and Azidoalkyl Vinyl Bromides: 1-Azadienes, Their Reactions with Diphenylketene, and Radical Cyclizations to Form Bi- And Tricyclic Lactams
Liddon, John T. R.,Lindsay-Scott, Peter J.,Robertson, Jeremy
, p. 13780 - 13793 (2019)
Azidoalkyl enol ethers undergo intramolecular 1,3-dipolar cycloaddition to generate stable triazolines; in contrast, the cycloadducts formed by heating analogous azidoalkyl vinyl bromides are unstable with respect to elimination of N2 and HBr, affording 1-azadienes (2-alkenyl cyclic imines). These primary products may be isolated or treated directly with diphenylketene to produce bi- and tricyclic 3,4-dihydropyridin-2(1H)-ones; similar ring systems may also be produced from the azadienes by N-acylation and radical cyclization.
Ruthenium-catalyzed reaction of α,β-unsaturated imines with carbon monoxide and alkenes leading to β,γ-unsaturated γ-butyrolactams: Involvement of direct carbonylation at olefinic C-H bonds as a key step
Chatani, Naoto,Kamitani, Akihito,Murai, Shinji
, p. 7014 - 7018 (2007/10/03)
The reaction of α,β-unsaturated imines with CO and alkenes in the presence of Ru3(CO)12 as a catalyst results in a three-component coupling reaction that gives α,α-disubstituted β,γ-unsaturated γ-butyrolactams. The reaction proceeds via a two-step sequence involving the initial formation of ketone derivatives by catalytic carbonylation at the β-olefinic C-H bonds of α,β-unsaturated imines, followed by the (uncatalyzed) intramolecular nucleophilic attack of the imine nitrogen on the ketonic carbon to generate a tetrahedral intermediate, which then undergoes a 1,2-ethyl migration. The reaction of a cyclic unsaturated imine, derived from the reaction of (1R)-(-)-myrtenal with tertbutylamine, gives a β-aminocyclopentene derivative, which is formed by an aldol-type condensation of the initially formed ketone, indicating the initial formation of ethyl ketone.
