24853-83-6Relevant articles and documents
Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues
Kurouchi, Hiroaki
supporting information, p. 653 - 658 (2021/02/06)
A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.
Synthesis of N-Heterocycles by Reductive Cyclization of Nitroalkenes Using Molybdenum Hexacarbonyl as Carbon Monoxide Surrogate
Su, Zhiyou,Liu, Bo,Liao, Hongze,Lin, Hou-Wen
supporting information, p. 4059 - 4066 (2020/06/21)
The development of a method that uses molybdenum hexacarbonyl [Mo(CO)6] as carbon monoxide (CO) surrogate for the palladium-catalyzed reductive cyclization of nitroalkenes into indoles or thienopyrroles is reported. Several types of nitroalkenes could be transformed into the desired products in excellent yields and in most cases with complete regioselectivities and higher yields than those previously reported with palladium/CO system.
Additive-free pd-catalyzed α-allylation of imine-containing heterocycles
Kljajic, Marko,Puschnig, Johannes G.,Weber, Hansj?rg,Breinbauer, Rolf
supporting information, p. 126 - 129 (2017/11/27)
An additive-free Pd-catalyzed α-allylation of different imino-group-ontaining heterocycles is reported. The activation of α-CH pronucleophiles (pKa (DMSO) > 25) occurs without the addition of strong bases or Lewis acids using only the Pd/Xantphos catalyst system. The reaction scope has been studied for various 5- and 6-membered nitrogen-containing heterocycles (yields up to 96%). Mechanistic investigations suggest an initial allylation of the imine-N followed by a Pd-catalyzed formal aza-Claisen rearrangement.
Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists
Naito, Ryo,Yonetoku, Yasuhiro,Okamoto, Yoshinori,Toyoshima, Akira,Ikeda, Ken,Takeuchi, Makoto
, p. 6597 - 6606 (2007/10/03)
In the course of continuing efforts to develop potent and bladder-selective muscarinic M3 receptor antagonists, quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives and related compounds were designed as conformationally restricted analogues of quinuclidin-3-yl benzhydrylcarbamate (8). Binding assays with rat muscarinic receptor subtypes revealed that the quinuclidin-3-yl 1-aryl-1,2,3,4- tetrahydroisoquinoline-2-carboxylate derivatives showed high affinities for the M3 receptor, and selectivity for the M3 receptor over the M2 receptor. Of these derivatives, (+)-(1S,3'R)-quinuclidin-3'-yl 1-phenyl-l,2,3,4-tetrahydroisoquinoline-2-carboxylate monohydrochloride (9b) exhibited almost the same inhibitory activity against bladder contraction to that of oxybutynin (1), and more than 10-fold selectivity for bladder contraction versus salivary secretion, demonstrating that 9b may be useful for the treatment of symptoms associated with overactive bladder without having side effects such as dry mouth.
A one-pot procedure for the synthesis of α-amino phosphonates from alkynes
Haak, Edgar,Bytschkov, Igor,Doye, Sven
, p. 457 - 463 (2007/10/03)
A new and highly flexible procedure for the synthesis of α,α-disubstituted α-amino phosphonates is described with disubstituted alkynes, primary amines and diethyl or dimethyl phosphite as starting materials. The reaction sequence, which is performed as a
The Cp2TiMe2-catalyzed intramolecular hydroamination/cyclization of aminoalkynes
Bytschkov, Igor,Doye, Sven
, p. 3715 - 3718 (2007/10/03)
Cp2TiMe2 has been found to be a competent catalyst for the intramolecular hydroamination/cyclization of aminoalkynes. In the presence of 5.0 mol% Cp2TiMe2, the hydroamination reactions proceed smoothly at 100-110°C to give five- and six-membered cyclic imines within 4-6 h. After subsequent reduction performed with zinc-modified NaBH3CN at room temperature cyclic amines can be isolated in good yields.
Inhibition of dopamine receptors by endogenous amines: Binding to striatal receptors and pharmacological effects on locomotor activity
Kawai, Hiroshi,Kotake, Yaichiro,Ohta, Shigeru
, p. 1669 - 1671 (2007/10/03)
Endogenous amine 1-benzyl-1,2,3,4-tetrahydroisoquinoline (1BnTIQ) derivatives are synthesized, and their activity for dopaminergic systems are evaluated in vitro and in vivo by receptor binding assay and pharmacological tests. It is proposed that 1BnTIQ d
Pharmaceutical compositions containing isoquinoline derivatives
-
, (2008/06/13)
Pharmaceutical compositions containing an isoquinoline derivative exhibit an excellent inhibitory action to an isozyme of phosphodiesterase of the type IV (PDEIV). The active component of the pharmaceutical composition is an isoquinoline derivative which is represented by the general formula: STR1 wherein R is an ethoxy group, or which is a pharmaceutically-acceptable salt of a compound represented by said formula. The isoquinoline derivatives have an excellent inhibitory action which is highly specific to PDEIV. They are highly useful as pharmaceuticals such as antidepressive agents, tranquilizers, antidemential agents, antiinflammatory agents, antiallergic agents, antiasthmatic agents, liver-protecting agents, and diuretic agents.
Titanium(III)-induced transformation of hydroxylamines to imines or secondary amines
Kodera,Watanabe,Imada,Murahashi
, p. 2542 - 1549 (2007/10/02)
N,N-Disubstituted and cyclic hydroxylamines can be converted into the corresponding imines efficiently upon treatment with anhydrons titanium trichloride in THF at room temperature. Similar treatment of N-allylhydroxylamines with anhydrous titanium trichloride gives 1-azadienes, which are versatile synthetie intermediates for aza-Diels-Alder reactions. On the other hand, the same hydroxylamines can be converted into the corresponding secondary amines upon treatment with aqueous titanium trichloride in methanol. It is noteworthy that optically active hydroxylamines, which have chirality at the α-position to nitrogen, can be converted into optically active secondary amines without loss of chirality. Dihydro-2(1H)-quinolinones can be prepared upon treatment of 1-hydroxy-3,4-dihydro-2(1H)-quinolinones with aqueous titanium trichloride. The substrates of N,N-disubstituted and cyclic hydroxylamines can be prepared readily upon treatment of nitrones with nucleophiles. Since nitrones can be prepared by metal-catalyzed oxidations of secondary amines with hydrogen peroxide, the present titanium(III)-promoted reaction of hydroxylamines will provide a convenient method for the synthesis of either α-substituted imines or amines from secondary amines.
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.
