1196-38-9Relevant articles and documents
Green Oxidation of Amines to Imines Based on the Development of Novel Catalytic Systems Using Molecular Oxygen or Hydrogen Peroxide
Marui, Kuniaki,Nomoto, Akihiro,Akashi, Haruo,Ogawa, Akiya
, p. 31 - 42 (2016)
Amines are transformed into the corresponding imines by environmentally benign catalytic oxidation reactions. Gaseous oxygen or hydrogen peroxide is used as the oxidant, and water is the only byproduct. When a vanadium complex is used as the catalyst in an ionic liquid, the amine oxidation successfully proceeds with recycling of the catalyst. Amine oxidation with hydrogen peroxide as an oxidant in water is also attained by using copper(II) sulfate as catalyst. In addition, photoinduced oxidation of amines to imines is conducted by using oxygen as the oxidant in the presence of a zinc-chlorin complex as catalyst.
Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones
Bansode, Ajay H.,Suryavanshi, Gurunath
, p. 1390 - 1400 (2021)
A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).
Synthesis of novel tricyclic aryltriazole-3-thione compounds
Cai, Cuiman,Plummer, Janet S.,Connor, David,Holsworth, Daniel D.,Edmunds, Jeremy J.
, p. 349 - 356 (2005)
A new synthetic protocol has been developed to provide entry into a series of novel tricyclic aryltriazole-3-thiones analogs. The classical reaction conditions of subjecting an arylhydrazide with thiophosgene to form the thioisocyanate intermediate and ultimately the corresponding aryltriazole-3-thione framework were not successful. However, using a combination of carbon disulfide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to form the thioisocyanate intermediate was found to produce the novel tricyclic aryltriazole-3-thiones (5, 8a-c) in good yield. Copyright Taylor & Francis, Inc.
Unusual dirhodium tetraacetate catalyzed intramolecular cyclization of isoquinoline diazoamides
Chelucci, Giorgio,Culeddu, Nicola,Saba, Antonio,Valenti, Raffaela
, p. 8269 - 8270 (1999)
The dirhodium(II) tetraacetate catalyzed decomposition of an isoquinoline diazoamide leads to the unexpected formation of a 1,3-oxazin-4-one ring which is consistent with a rare example of an intramolecular metal-carbene hydride-abstraction mechanism.
Selective oxidation of benzylic hydrocarbons to carbonyl compounds catalyzed by Mn(III) salen complexes
Lee, Nam Ho,Lee, Chang-Seob,Jung, Duk-Sang
, p. 1385 - 1388 (1998)
Selective oxidation of benzylic hydrocarbons to the carbonyl compounds was achieved using a racemic Mn(III) salen complex 1 as the catalyst. The reaction proceeds in good yields under mild reaction conditions using iodosobenzene or aq. sodium hypochlorite as a stoichiometric oxidant.
Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
Li, Junxuan,Zhou, Jinlei,Wang, Yumei,Yu, Yue,Liu, Qiang,Yang, Tilong,Chen, Huoji,Cao, Hua
, p. 68 - 74 (2021/11/16)
Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]
Synthesis, in vitro cytotoxicity, and molecular docking study of novel 3,4-dihydroisoquinolin-1(2H)-one based piperlongumine analogues
Kulkarni, Mahesh R.,Lad, Nitin P.,Khedkar, Vijay M.,Gaikwad, Nitin D.
, p. 1359 - 1370 (2021/04/09)
With the aim of expanding the scope of SAR on piperlongumine (PL), a naturally occurring anticancer molecule, we have designed a novel hybrid molecule bearing 3,4-dihydroisoquinolin-1(2H)-one and trans-cinnamic acids. The structure, based on hybridization strategy, is used for hybridization of naturally occurring scaffolds. We have synthesized 14 hybrid molecules by coupling 3,4-dihydroisoquinolin-1(2H)-one core with cinnamic acids using the mix anhydride approach. The newly synthesized inhibitors were evaluated for cell viability against breast cancer MCF-7 and cervical cancer HeLa cell lines. Furthermore, the active compounds were screened for their potential in breast cancer MDA-MB-231, cervical cancer C33A cell lines, prostate cancer DU-145, PC-3, and normal VERO cells. From the series, compound 10g was seen to inhibit MCF-7 cell growth significantly with GI50 50 = 20 μM) and C33A (GI50 = 3.2 μM). While the inhibitor 10i inhibits MCF-7 breast cancer cell growth GI50 = 3.42 μM along with inhibition of cell growth in MDA-MB-231 (GI50 = 30 μM), HeLa (GI50 = 7.67 μM), C33A (GI50 = 13 μM), DU-145 (GI50 = 6.45 μM), PC-3 (GI50 = 8.68 μM), and VERO (GI50 = 2.93 μM), respectively. Furthermore, molecular docking study demonstrated these compounds could bind tightly to the colchicine domain of tubulin through a network of favorable steric and electrostatic interactions and thus act as a tubulin polymerization inhibitor.
