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3382-18-1Relevant academic research and scientific papers
One-step route to tricyclic fused 1,2,3,4-tetrahydro-isoquinoline systems via the castagnoli–cushman protocol
Burdzhiev, Nikola,Pashev, Aleksandar,Stanoeva, Elena
, p. 1456 - 1464 (2020)
The Castagnoli–Cushman reaction of 3,4-dihydroisoquinolines with glutaric anhydride, its oxygen and sulfur analogues was investigated as a one-step approach to the benzo[a]quinolizidine system and its heterocyclic analogs. An extension towards the pyrrolo[2,1-a]isoquinoline system was achieved with the use of succinic anhydride. The results are evidence of an unexplored method for the access of the aforementioned tricyclic annelated systems incorporating a bridgehead nitrogen atom. The structures and relative configurations of the new compounds were established by means of 1D and 2D NMR techniques. The reactions between 1-methyldihydroisoquinoline and glutaric, diglycolic and succinic anhydrides yielded unexpected isoquinoline derivatives containing an exocyclic double bond. The compounds prepared bear the potential to become building blocks for future synthetic bioactive molecules.
Integrating Hydrogen Production with Aqueous Selective Semi-Dehydrogenation of Tetrahydroisoquinolines over a Ni2P Bifunctional Electrode
Huang, Chenqi,Huang, Yi,Liu, Cuibo,Yu, Yifu,Zhang, Bin
, p. 12014 - 12017 (2019)
Exploring an alternative anodic reaction to produce value-added chemicals with high selectivity, especially integrated with promoted hydrogen generation, is desirable. Herein, a selective semi-dehydrogenation of tetrahydroisoquinolines (THIQs) is demonstrated to replace the oxygen evolution reaction (OER) for boosting H2 evolution reaction (HER) in water over a Ni2P nanosheet electrode. The value-added semi-dehydrogenation products, dihydroisoquinolines (DHIQs), can be selectively obtained with high yields at the anode. The controllable semi-dehydrogenation is attributed to the in situ formed NiII/NiIII redox active species. Such a strategy can deliver a variety of DHIQs bearing electron-withdrawing/donating groups in good yields and excellent selectivities, and can be applied to gram-scale synthesis. A two-electrode Ni2P bifunctional electrolyzer can produce both H2 and DHIQs with robust stability and high Faradaic efficiencies at a much lower cell voltage than that of overall water splitting.
Integrating photocatalytic reduction of CO2 with selective oxidation of tetrahydroisoquinoline over InP–In2O3 Z-scheme p-n junction
Zhao, Bohang,Huang, Yi,Liu, Dali,Yu, Yifu,Zhang, Bin
, p. 28 - 34 (2020)
The development of a facile strategy to construct stable hierarchal porous heterogeneous photocatalysts remains a great challenge for efficient CO2 reduction. Additionally, hole-trapping sacrificial agents (e.g., triethanolamine, triethylamine, and methanol) are mostly necessary, which produce useless chemicals, and thus cause costs/environmental concerns. Therefore, utilizing oxidation ability of holes to develop an alternative photooxidation reaction to produce value-added chemicals, especially coupled with CO2 photoreduction, is highly desirable. Here, an in situ partial phosphating method of In2O3 is reported for synthesizing InP–In2O3 p-n junction. A highly selective photooxidation of tetrahydroisoquinoline (THIQ) into value-added dihydroisoquinoline (DHIQ) is to replace the hole driven oxidation of typical sacrificial agents. Meanwhile, the photoelectrons of InP–In2O3 p-n junction can induce the efficient photoreduction of CO2 to CO with high selectivity and stability. The evolution rates of DHIQ and CO are 2 and 3.8 times higher than those of the corresponding In2O3 n-type precursor, respectively. In situ irradiated X-ray photoelectron spectroscopy and electron spin resonance are utilized to confirm that the direct Z-scheme mechanism of InP–In2O3 p-n junction accelerate the efficient separation of photocarriers.
Accelerating H2 Evolution by Anodic Semi-dehydrogenation of Tetrahydroisoquinolines in Water over Co3O4 Nanoribbon Arrays Decorated Nickel Foam
Xiang, Ming,Xu, Zhihua,Wang, Jinghao,Yang, Xiaoqiu,Yan, Zhaoxiong
supporting information, p. 7502 - 7506 (2021/04/21)
Coupling the H2 evolution reaction in water with thermodynamically favorable organic oxidation reactions is highly desirable, because it can enhance the energy conversion efficiency compared with electrocatalytic water splitting, and produce value-added chemicals instead of O2 in the anodic reaction. Herein, Co3O4 nanoribbon arrays in situ grown on nickel foam (Co3O4@NF) was employed as an effective electrocatalyst for the selective oxidation of tetrahydroisoquinolines (THIQs). Various value-added semi-dehydrogenation products including dihydroisoquinolines with electro-deficient or -rich groups could be obtained with moderate yields and faradaic efficiencies. Benefitting from the rich surface active sites of Co3O4@NF, a two-electrode (Co3O4@NF||Pt) electrolytic system drove a benchmark current density of 10 mA cm?2 at a cell voltage as low as 1.446 V in 1.0 M KOH aqueous solution containing 0.02 M THIQ, which was reduced by 174 mV in comparison with that of overall water splitting.
Peganumine A alkaloid structure simplifier and application thereof
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Paragraph 0037-0038; 0042-0044, (2021/06/26)
The invention discloses a Peganumine A alkaloid structure simplifier, a stereoisomer or a pharmaceutical salt thereof. The structure is shown in the following general formula: each substituent group is defined in the specification. The simplified structure of the Peganumine A alkaloid provided by the invention has a relatively obvious proliferation inhibition effect on liver cancer HepG2, lung cancer A549 and intestinal cancer HCT116, and the anti-tumor activity of part of compounds is higher than the anti-liver cancer HepG2 activity of Peganumine A reported in literatures.
Enantioselective synthesis of 1-aryl tetrahydroisoquinolines by the rhodium-catalyzed reaction of 3,4-dihydroisoquinolinium tetraarylborates
Li, Wei-Sian,Kuo, Ting-Shen,Wu, Ping-Yu,Chen, Chien-Tien,Wu, Hsyueh-Liang
supporting information, p. 1141 - 1146 (2021/02/16)
The 1-aryl tetrahydroisoquinolines (1-aryl THIQs) are omnipresent in biologically active molecules. Here we report on the direct asymmetric synthesis of these valuable compounds via the reaction of 3,4-dihydroisoquinolinium tetraarylborates. The dual roles of anionic tetraarylborates, which function as both prenucleophiles and stabilizers of 3,4-dihydroisoquinolinium cations, enable this rhodium(I)-catalyzed protocol to convergently provide enantioenriched 1-aryl THIQs in good yields (≤95%) with ≤97% ee, as demonstrated by the formal synthesis of (?)-solifenacin and the facile synthesis of (?)-Cryptostyline I.
Gold(I)-Catalyzed Cyclization-3-Aza-Cope-Mannich Cascade and Its Application to the Synthesis of Cephalotaxine
Sakai, Takeo,Okumura, Chise,Futamura, Masatoshi,Noda, Naotaka,Nagae, Akari,Kitamoto, Chiharu,Kamiya, Madoka,Mori, Yuji
supporting information, p. 4391 - 4395 (2021/05/26)
The discovery of a new gold(I)-catalyzed cascade reaction involving cyclization onto a vinylammonium, 3-aza-Cope rearrangement, and Mannich cyclization is reported. A variety of fused nitrogen heterocycles were prepared from simple cyclic tertiary amines using 1-5 mol % of a AuCl(PPh3)/Ag[C5(CN)5] cocatalyst system. The developed reaction was used in a study aimed at synthesizing cephalotaxine. A five-step operation from norhydrastinine provided demethylcephalotaxinone in 39.1% overall yield, which was transformed to (-)-cephalotaxine in two steps.
One-pot method for preparing 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride
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, (2020/03/09)
The invention provides a one-pot method for preparing 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride. The method comprises the following steps: with 3,4-dimethoxyphenylethylamine and a formylation reagent as raw materials, carrying out a reaction to prepare an intermediate solution, and subjecting the prepared intermediate solution to a further reaction with a solution containing oxalyl chloride; after the reaction is finished, adding phosphotungstic acid for catalytic cyclization; then adding an alcohol solvent for oxalic acid removal to obtain a target product; and finally, cooling andcrystallizing a reaction solution, carrying out filtering, leaching a filter cake, and carrying out drying to obtain the target product. According to the invention, process operation is extremely simple, and the 6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride (with a purity of 99.0% or above and a single impurity content of less than or equal to 0.15%) meeting the cGMP quality index requirements and having yield of 75% or above can be obtained only by cooling, filtering, leaching and drying after the one-pot reaction, so process material, manpower and equipment costs are obviously reduced;the process safety level of the method is obviously improved; waste materials are few; and good industrial application prospects are obtained.
Cyclopropenones in the synthesis of indolizidine, pyrrolo[2,1-a]isoquinoline and indolizino[8,7-b]indole alkaloids
Jamshaid, Faisal,Kondakal, Vishnu V.R.,Newman, C. Declan,Dobson, Rhianne,Jo?o, Heidi,Rice, Craig R.,Mwansa, Joseph M.,Thapa, Bimod,Hemming, Karl
supporting information, (2020/09/18)
An attempted synthesis of the indolizidine natural product castanospermine resulted in the successful addition of cyclopropenone to a sugar-derived poly-hydroxylated cyclic imine to give an indolizidinone product, but with the installation of an extra hydroxy group at the castanospermine 8a-bridgehead position. This was also observed in our previous approach to the australine and hyacinthacine pyrrolizidine natural products. The same oxidative phenomenon occurred during the synthesis of pyrrolo[1,2-a]isoquinolines from the reaction of aldimine dihydroisoquinolines with cyclopropenones, whereas ketimine based dihydroisoquinolines gave pyrrolo[1,2-a]isoquinolines without bridgehead oxidation. These results may have some significance for the origins of the bridgehead hydroxy natural products jenamidine B1/B2, clazamycin A/B and legonmycin A/B. The precursor cyclic aldimine for the synthesis of the indolizino[8,7-b]indoles gave dimeric indolizino[8,7-b]indoles, whereas the corresponding cyclic ketimines behaved as expected and gave the indolizino[8,7-b]indole core after reaction with cyclopropenones.
Tetrabenazine intermediate as well as synthesis method and application thereof as, well as intermediate product for synthesis (by machine translation)
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Paragraph 0082; 0086-0088; 0091; 0095-0098-0099-0100; 0103, (2020/02/14)
The invention belongs to, the field of drug synthesis, and particularly relates to a butanaphenazine, intermediate and a synthesis method, thereof, as well as a synthesis: method 3,4 - thereof; and, 6,7 . (by machine translation)
