120086-32-0Relevant academic research and scientific papers
A simple iridicycle catalyst for efficient transfer hydrogenation of n-heterocycles in water
Talwar, Dinesh,Li, Ho Yin,Durham, Emma,Xiao, Jianliang
supporting information, p. 5370 - 5379 (2015/03/30)
A cyclometalated iridium complex is shown to catalyse the transfer hydrogenation of various nitrogen heterocycles, including but not limited to quinolines, isoquinolines, indoles and pyridinium salts, in an aqueous solution of HCO2H/HCO2Na under mild conditions. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), with catalyst loadings as low as 0.01 mol % being feasible. Mechanistic investigation of the quinoline reduction suggests that the transfer hydrogenation proceeds via both 1,2- and 1,4-addition pathways, with the catalytic turnover being limited by the step of hydride transfer. An easily accessible iridicycle catalyst effects the transfer hydrogenation of a wide variety of N-heterocycles in water, including quinolines, isoquinolines, indoles, quinoxalines, and pyridines. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), even with low catalyst loadings.
Synthesis of benzoazocines from substituted tetrahydroisoquinolines and activated alkynes in a tetrahydropyridine ring expansion
Voskressensky, Leonid G.,Listratova, Anna V.,Borisova, Tatiana N.,Alexandrov, Grigoriy G.,Varlamov, Alexey V.
, p. 6106 - 6117 (2008/09/17)
Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Tandem enlargement of the tetrahydropyridine ring in 1-aryl-tetrahydroisoquinolines using activated alkynes-a new and effective synthesis of benzoazocines
Voskressensky, Leonid G.,Borisova, Tatiana N.,Listratova, Anna V.,Kulikova, Larisa N.,Titov, Alexander A.,Varlamov, Alexey V.
, p. 4585 - 4589 (2007/10/03)
Tetrahydroisoquinolines 3a-e underwent piperidine ring enlargement under the action of activated alkynes, giving benzoazocines 4, 5 and 7-11 in high yields.
Phencyclidine-like Effects of Tetrahydroisoquinolines and Related Compounds
Gray, Nancy M.,Cheng, Brian K.,Mick, Stephen J.,Lair, Cecelia M.,Contreras, Patricia C.
, p. 1242 - 1248 (2007/10/02)
A series of 1,2,3,4-tetrahydroisoquinolines, tetrahydrothienopyridines, and related compounds were evaluated for their ability to inhibit binding of -1--N-allylnormetazocine to phencyclidine (PCP) and ? receptors, respectively.A representative series of compounds was evaluated in behavioral assays to determine the ability of the compounds to induce PCP-like stereotyped behavior and ataxia.All of the compounds caused stereotyped behavior and ataxia, indicating their agonist actions at the PCP site.
