6628-86-0Relevant articles and documents
Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent
Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro
supporting information, p. 1553 - 1558 (2021/02/26)
Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.
Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6121 - 6125 (2021/08/16)
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
Iron-Catalyzed Aerobic Oxidation of Alcohols: Lower Cost and Improved Selectivity
Jiang, Xingguo,Liu, Jinxian,Ma, Shengming
, p. 825 - 835 (2019/05/02)
An aerobic oxidation reaction of alcohols toward aldehydes or ketones using catalytic amounts of Fe(NO3)3·9H2O, 4-OH-TEMPO, and NaCl has been developed. Compared with the former catalytic system with TEMPO developed in this group, the new protocol using 4-OH-TEMPO, which is much cheaper on an industrial scale, accomplished the transformation with a higher selectivity, especially for aliphatic alcohols toward aldehydes. α,β-Unsaturated alkynals or alkynones can be efficiently synthesized from propargyl alcohols, which has been much less studied in the literature.
Pyrrolo[2,1-c][1,4] benzodiazepine-3,11-diones protect SHSY-5Y cells from Cd-induced apoptosis involving suppression of endoplasmic reticulum stress
Ma, Chao,Du, Ke,Zhao, Ying,Zhang, Linkui,Hu, Baichun,Cheng, Maosheng
, p. 5151 - 5158 (2018/09/27)
Cadmium (Cd) is a potent toxic heavy metal, some studies showed that Cd-induced apoptosis is through ER stress pathway. Compounds of pyrrolo[2,1–c][1,4]benzodiazepine (PBD)-3,11-diones were discovered as potent neuroprotective agents against Cd-induced toxicity in SH-SY5Y cells for the first time. In this study, twenty-six PBD-3,11-dione derivatives were synthesized and evaluated for their neuroprotective activity against Cd-induced toxicity by CCK-8 assay. Their preliminary SARs studies indicated that various substituents were tolerated on the benzene ring, and alkyl heterocycles groups at the N10-position of the PBD-3,11-dione scaffold were important for the activities. Among them, compound 13c exhibited the best activity (cell viability = 68.6%, 25 μM). Furthermore, we found that the compound 13c could inhibit cadmium-induced cell apoptosis with the downregulation of the ER stress markers GRP78, CHOP, cleaved-caspase12 and cleaved-caspase3 through western blotting. The results of in silico evaluation of ADME/T properties showed that 13c exhibited medium BBB penetration level and promising toxicity profiles. These results proved the potential of 13c as a promising lead compound against Cd-induced neurotoxicity.
Studies on Iron-Catalyzed Aerobic Oxidation of Benzylic Alcohols to Carboxylic Acids
Jiang, Xingguo,Ma, Shengming
, p. 1629 - 1639 (2018/02/26)
A comprehensive study on aerobic oxidation of benzylic alcohols to carboxylic acids with a catalytic amount each of Fe(NO 3) 3 ·9H 2 O, TEMPO, and KCl is conducted. Various synthetically useful functional groups are well tolerated in the reaction. Distinct electronic and steric effects are observed in the reaction: electron-withdrawing groups accelerate the reaction while electron-donating groups make the reaction slower, and ortho -substituted substrates react slower than meta -substituted substrates. Several large-scale reactions (100 mmol) are conducted using a slow air flow of 30 mL/min to demonstrate the practicality of this method in an academic laboratory.
A O-nitrobenzaldehyde synthetic method of compound
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Paragraph 0065; 0066; 0067; 0070; 0071, (2016/10/07)
The invention provides a preparation method for an o-nitrobenzaldehyde compound. The method directly taking benzaldehyde compounds as starting raw materials comprises the following steps: firstly, converting a formyl group into an O-methyl oximido; secondly, taking divalent palladium salt as a catalyst, and realizing the carbon-hydrogen bond activation single nitration reaction on an o-position of an oximido under the condition that both an oxidant and a nitration agent exist; finally, removing the O-methyl oximido by using strong organic acid to obtain the o-nitrobenzaldehyde compound. The nitration method provided by the invention has the advantage of specificity in the o-position of a nitration position, the reaction process is safe and environment-friendly, the substrate is excellent in adaptability, and various substituents can realize o-position nitration; various benzaldehyde is directly taken as raw materials, so that the reaction steps are simple, and the synthesizing method is a novel route for synthesizing various o-nitrobenzaldehyde compounds containing substituents.
Regiospecific synthesis of substituted 2-nitrobenzaldehydes from benzaldehydes through palladium-catalyzed chelation-assisted C-H nitration
Zhang, Wei,Wu, Degui,Zhang, Jian,Liu, Yunkui
, p. 5827 - 5835 (2014/10/15)
A regiospecific synthesis of substituted 2-nitrobenzaldehydes from substituted benzaldehydes has been developed that involves a three-step process with palladium-catalyzed chelation-assisted C-H nitration as the key step. In the process, O-methyl aldoxime serves as a removable directing group for the palladium-catalyzed ortho-nitration of substituted benzaldoximes and it can be removed in subsequent conversion of the resulting 2-nitrobenzaldoximes into 2-nitrobenzaldehydes.
2,4-DIAMINO-6,7-DIHYDRO-5H-PYRROLO[2,3]PYRIMIDINE DERIVATIVES AS FAK/Pyk2 INHIBITORS
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Page/Page column 49-50, (2012/07/27)
The invention relates to a novel class of 2,4-diamino-6,7-dihydro-5H-pyrrolo[2,3]pyrimidine derivatives as a FAK and/or Pyk2 inhibitor, to a process for their preparation, and to a composition thereof, as well as to use of the compounds for the inhibiting FAK and/or Pyk2 and method for the treatment of a FAK and/ or Pyk2 mediated disorder or disease.
9-Benzylidene-9H-fluorene derivatives linked to Monoaza-15-crown-5: Synthesis and metal ion sensing
Cao, Jing,Li, Yang,Feng, Junxiang
scheme or table, p. 1571 - 1574 (2012/09/07)
Two kinds of novel styryl chemosensory 2-FMNC and 3-FMNC, were designed and synthesized by an apporiate introduction of 9-benzylidene-9H-fluorene group as fluorophore with the aim at avoiding photoisomerisation. These 9-benzylidene-9H-fluorene derivatives showed the similar selectivity and sensitivity upon addition of metal ions. The sensitivity of FMNC to alkaline earth metal ions was Ba2+>Sr2+>Ca 2+≈Mg2+. Copyright
Highly practical copper(I)/TEMPO catalyst system for chemoselective aerobic oxidation of primary alcohols
Hoover, Jessica M.,Stahl, Shannon S.
supporting information; experimental part, p. 16901 - 16910 (2011/12/04)
Aerobic oxidation reactions have been the focus of considerable attention, but their use in mainstream organic chemistry has been constrained by limitations in their synthetic scope and by practical factors, such as the use of pure O2 as the oxidant or complex catalyst synthesis. Here, we report a new (bpy)CuI/TEMPO catalyst system that enables efficient and selective aerobic oxidation of a broad range of primary alcohols, including allylic, benzylic, and aliphatic derivatives, to the corresponding aldehydes using readily available reagents, at room temperature with ambient air as the oxidant. The catalyst system is compatible with a wide range of functional groups and the high selectivity for 1° alcohols enables selective oxidation of diols that lack protecting groups.
