- A convenient synthesis of tertiary amines by alkylation of secondary amines with alkyl halides in the presence of potassium hydride and triethylamine
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N-Alkylation of secondary amines with alkyl halides in the presence of potassium hydride and triethylamine gave corresponding tertiary amines in satisfactory yields.
- Mohri,Suzuki,Usui,Isobe,Tsuda
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- Gold Catalyzed Photoredox C1-Alkynylation of N-Alkyl-1,2,3,4- tetrahydroisoquinolines by 1-Bromoalkynes with UVA LED Light
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A synthetic method that combines [Au2(m-dppm)2]Cl2 (dppm=bis(diphenylphosphanyl)methane) and UVA LED (LED=light emitting diode) light (365 nm) to catalyze the regioselective C1-alkynylation of N-alkyl-1,2,3,4-tetrahydroisoquinolines (THIQs) with alkynyl bromides is described. The reaction mechanism was delineated to involve a reductive quench pathway to generate the two posited radical species of the nitrogen-containing heterocycle and organic halide. In contrast, radical formation via an oxidative quench pathway was suggested to be operative in analogous control experiments with a 1-iodoalkyne. The usefulness of this carbon-carbon bond forming strategy was also exemplified by its application to the formal synthesis of the opioid analgesic drug methopholine and synthesis of a protoberberine alkaloid derivative.
- Zhao, Yichao,Jin, Jianwen,Chan, Philip Wai Hong
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supporting information
p. 1313 - 1321
(2019/06/03)
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- Visible-Light-Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide
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We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.
- Tan, Wei,Wang, Cuihong,Jiang, Xuefeng
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supporting information
p. 1234 - 1238
(2019/11/21)
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- Tropylium-Promoted Oxidative Functionalization of Tetrahydroisoquinolines
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Structural modification of the tetrahydroisoquinoline (THIQ) framework is of significant interest to organic chemists due to its central role in heterocyclic and medicinal chemistry. Here we demonstrate an efficient metal-free method for the oxidative fun
- Oss, Giulia,De Vos, Sander D.,Luc, Kevin N. H.,Harper, Jason B.,Nguyen, Thanh V.
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p. 1000 - 1010
(2018/01/28)
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- Modified B-alkylcatecholboranes as radical precursors
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Generation of radicals from B-alkylcatecholboranes represents an efficient tin-free procedure for the generation of alkyl radicals. A modified version of this method has been developed. The simple catechol is replaced by a dihydroxylated tetrahydroisoquin
- Luethy, Monique,Darmency, Vincent,Renaud, Philippe
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supporting information; experimental part
p. 547 - 552
(2011/03/22)
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- N-substituted isoquinoline derivatives as potential AChE inhibitors
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(Chemical Equation Presented) N-substituted donepezil-related isoquinolines have been prepared as potential acetylcholinesterase inhibitors (AChEIs). Microwave assisted procedures and solution-phase parallel synthesis were chosen to optimize the synthetic approach and improve the yields. All synthesized compounds were tested for their AChE inhibitory activity by colorimetric Ellman method and some of them (10, 13, and 28) displayed low inhibitory effects at μM concentrations.
- Gitto, Rosaria,De Luca, Laura,Ferro, Stefania,De Grazia, Sara,Di Giorgio, Rosa Maria,Festa, Filomena,De Luca, Grazia
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experimental part
p. 54 - 62
(2010/05/03)
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- Unprecedented FeCl3·6 H2O-promoted skeleton rearrangement of 1-Aryl2,3,4,5-tetrahydro-1H-3-benzazepines: A new strategy for the synthesis of C1 quaternary tetrahydroisoquinolines
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A study was conducted to demonstrate that 1-aryl-tetrahydroisoquinolines were prepared through a skeleton-rearrangement promoted by FeCl 3·6H2O. 7,8-dimethoxy-3-methyl-1-(m-tolyl)-2,3,4,5- tetrahydro-1H-benzo[d]azepine was selected a
- Zhang, Jing,Zhang, Ao
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supporting information; experimental part
p. 11119 - 11122
(2010/04/26)
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- SYNTHESES BASED ON &β-PHENYLETHYLAMINES V. SYNTHESIS AND PRELIMINARY PHARMACOLOGICAL SCREENING OF SOME PHENYLALKYLAMINES AND N-BENZYLTETRAHYDROISOQUINOLINES
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The synthetic series of substituted N-benzyltetrahydroisoquinolines has been continued and the pharmacological activities of the compounds obtained have been investigated.
- Vinogradova, V. I.,Golodnyuk, T. I.,Yunusov, M. S.,Suleimanova, G. A.,Tulyaganov, N.
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p. 654 - 657
(2007/10/02)
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- 2-(aminobenzyl)-1,2,3,4-tetrahydroisoquinolines: A new class of α2-adrenergic receptor antagonists
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A new class of α2-adrenergic receptor antagonists, the 2-(aminobenzyl)-1,2,3,4-tetrahydroisoquinolines 4 and their derivatives, is described. Two synthetic routes are reported. An investigation of the structure-activity relationships including various substitutions of the isoquinoline moiety and the benzyl group is discussed. The affinity and selectivity for both α1- and α2-adrenoceptors was defined by studying the displacement of [3H]-prazosin (α1-sites) and [3H]-yohimbine (α2-sites) from rat brain membranes. The 2-(2-amino-3,4-dimethoxybenzyl)-6-methoxy-1,2,3,4- tetrahydroisoquinoline 4a presented affinity and selectivity close to yohimbine. In functional experiments the α-adrenoceptor blocking properties of 4a have been evaluated on isolated rat aorta and on the twitch responses of the isolated rat vas deferens.
- Stambach,Kanmacher,Jung,Schott,Heitz,Stoclet
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p. 427 - 432
(2007/10/02)
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- A Facile Sythesis of 1,2,3,4-Tetrahydroisoquinolines Through Cyclization of O,N-Acetals
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A mild and efficient method for the synthesis of 1,2,3,4-tetrahydroisoquinolines by a modified Pictet-Spengler reaction involving Lewis acid-mediated cyclization of O,N-acetals is described.
- Kubo, Akinori,Saito, Naoki,Kawakami, Nanko,Matsuyama, Yasuo,Miwa, Teruyo
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p. 824 - 827
(2007/10/02)
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- Synthesis, Positive and Negative Ion Mass Spectra and Microbial Activity of N-Benzyltetrahydroisoquinolines
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Substituted N-benzyltetrahydroisoquinolines (5-11) have been synthesised and their positive and negative ion mass spectra studied.The M+. of these compounds are fairly stable and abundant RDA fragment ions (often corresponding to the base peaks) are observed in their positive ion EI spectra.However, under negative ion conditions these molecules fragment in a similar way as that of 1-benzyltetrahydroisoquinolines.The base (5-11) hydrochlorides when tested against a number of fungi and bacteria do not exhibit any promising activity.
- Pant, Pushpa,Madhusudanan, K. P.,Bhakuni, D. S.
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p. 630 - 633
(2007/10/02)
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- A Mild and Chemoselective Reduction of Cyclic Iminium Salts
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N-Substituted cyclic iminium salts are conveniently reduced to the corresponding tertiary amines in good yields by reaction with tributylstannane in methanol at room temperature.A variety of functional groups (such as ketonic groups) present in the molecule are not affected under these conditions.
- Palmisano, Giovanni,Lesma Giordano,Nali, Micaela,Rindone, Bruno,Tollari, Stefano
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p. 1072 - 1074
(2007/10/02)
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