18861-57-9Relevant academic research and scientific papers
Organic-inorganic hybrid silica materials containing imidazolium and dihydroimidazolium salts as recyclable organocatalysts for Knoevenagel condensations
Trilla, Montserrat,Pleixats, Roser,Man, Michel Wong Chi,Bied, Catherine
, p. 1815 - 1820 (2009)
Organic-inorganic hybrid silica materials containing imidazolium and dihydroimidazolium salts prepared from monosilylated and disilylated monomers by sol-gel methodologies are active and reusable organocatalysts for the Knoevenagel condensation of aromatic aldehydes with malononitrile and ethyl cyanoacetate under solvent-free conditions. Our immobilized systems present higher activities than related homogeneous bis-imidazolium salts, showing the cooperative effect of the matrix surface and the additional advantage of easy recycling. The best performances were obtained with the material derived from polycondensation of a disilylated dihydroimidazolium salt in the absence of tetraethoxysilane (TEOS). The Royal Society of Chemistry 2009.
Transition metal polyhydrides-catalyzed addition of activated nitriles to aldehydes and ketones via Knoevenagel condensation
Lin, Yingrui,Zhu, Xianchao,Xiang, Min
, p. 215 - 218 (1993)
Transition metal polyhydrides and dihydrogen complexes catalyze Knoevenagel addition of cyanoacetate to aldehydes and ketones under neutral and mild conditions, the adducts undergo dehydration to give substituted (E)-2-cyano-α,β-unsaturated esters exclusively.
New pyridinecarbonitriles from fluoro arylpropenones
Mishriky, N.,Asaad, F. M.,Ibrahim, Y. A.,Girgis, A. S.
, p. 35 - 39 (1994)
The facile synthetic approaches to 3-pyridinecarbonitriles are described.The first approach involves the base-catalyzed transformation of 4-hydroxy-1,1-cyclohexanedicarbonitrile 2a into 4a, b.The other route involves the base-catalyzed multi-step one-pot reaction of aryl methyl ketones with the appropriate arylidenemalononitriles 6, 11a, b.Careful study of the synthesis of 2a, b from 1a, b revealed the importance of controlling the reaction conditions.Thus, 1,7-dioxo-4,4-heptanedicarbonitriles 3a, b or 3-pyridinecarbonitrile 4a were obtained in addition to the desired 2a, b under different basic conditions.
Synthesis, biological evaluation and molecular docking studies of 4Hbenzo[ h]chromenes, 7H-benzo[h]chromeno[2,3-d]pyrimidines as Antitumor Agents
Halawa, Ahmed H.,Fouda, Ahmed M.,Al-Dies, Al-Anood M.,El-Agrody, Ahmed M.
, p. 77 - 88 (2016)
In the present study, novel derivatives of 7H-benzo[h]chromeno[2,3-d]pyrimidine were prepared from 4H-benzo[h]chromene-3-carbonitrile and ethyl 4H-benzo[h]chromene-3-carboxylate derivatives and were evaluated as potential cytotoxic agents. The structures of the synthesized compounds were established on the basis of spectral data, IR, 1H NMR, 13C NMR and MS data. The invitro antitumor activity of the synthesized compounds was investigated in comparison with the standard drug Colchicine using MTT colorimetric assay. We explored the Structure-Activity Relationship (SAR) of 4Hbenzo[ h]chromenes with modification at the 2- or 3-positions and 2,3-positions. It was found that some compounds showed good antitumor activity against the cell lines MCF-7, HCT-116 and HepG-2 as compared with Colchicine. The SAR study revealed that the antitumor activity of the synthesized compounds were significantly affected by the lipophilicity (hydrophobic or hydrophilic) of the substituent at 2- or 3-positions and 2,3-positions.
Highly Active Copper(I)-Chalcogenone Catalyzed Knoevenagel Condensation Reaction Using Various Aldehydes and Active Methylene Compounds
Mannarsamy, Maruthupandi,Prabusankar, Ganesan
, (2021/10/05)
First copper(I) chalcogenones catalysed Knoevenagel Condensation reactions have been reported. No illustration of the utilization of this copper-chalcogenone complex class in Knoevenagel Condensation catalysis can be found. Thus, copper(I) bis(benzimidazole-2-chalcogenone) catalysts [Cu(L1)4]+BF4? (1) and [Cu(L2)4]+BF4? (2) (L1 = bis(1-isopropyl-benzimidazole-2-selone)-3-ethyl; L2 = bis(1-isopropyl-benzimidazole-2-thione)-3-ethyl) have been utilized as catalysts in the Knoevenagel Condensation reactions. These copper(I) chalcogenone catalysts have shown high efficiency for the catalytic Knoevenagel Condensation of aryl aldehydes and active methylene compounds. In particular, complex 2, exhibit the best catalytic activities. The scope of the catalytic reactions has been investigated with 22 different molecules. The excellent catalytic activity has been depicted for various types of substrates with either electron-rich or deficient aryl aldehydes. The present investigation features relatively mild reaction conditions with good functional group tolerance and excellent yields. Graphic Abstract: The first copper(I)-chalcogenone complexes catalysed Knoevenagel Condensation reactions?have also been investigated, and revealed the best catalytic activities. [Figure not available: see fulltext.]
Ball-Milling-Enabled Reactivity of Manganese Metal**
Bolt, Robert R. A.,Browne, Duncan L.,Howard, Joseph L.,Khan, Adam,Magri, Giuseppina,Morrill, Louis C.,Nicholson, William I.,Richards, Emma,Seastram, Alex C.
supporting information, p. 23128 - 23133 (2021/09/20)
Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.
Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss
Liu, Xiaoguang,Flores, Aimee A.,Situ, Lisa,Gu, Wen,Ding, Hui,Christofk, Heather R.,Lowry, William E.,Jung, Michael E.
, p. 2046 - 2063 (2021/02/16)
Herein, we report the synthesis and evaluation of novel analogues of UK-5099 both in vitro and in vivo for the development of mitochondrial pyruvate carrier (MPC) inhibitors to treat hair loss. A comprehensive understanding of the structure-activity relationship was obtained by varying four positions of the hit compound, namely, the alkyl group on the N1 position, substituents on the indole core, various aromatic and heteroaromatic core structures, and various Michael acceptors. The major discovery was that the inhibitors with a 3,5-bis(trifluoromethyl)benzyl group at the N1 position were shown to have much better activity than JXL001 (UK-5099) to increase cellular lactate production. Additionally, analogue JXL069, possessing a 7-azaindole heterocycle, was also shown to have significant MPC inhibition activity, which further increases the chemical space for drug design. Finally, more than 10 analogues were tested on shaved mice by topical treatment and promoted obvious hair growth on mice.
trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines
Meyer, Maximilian,Peri?, Milica,Sch?mberg, Fritz,Vilotijevi?, Ivan
supporting information, (2021/10/04)
trans-Selective hydrocyanation of ynoates and ynones in the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic conditions only. In these reactions, TMSCN reacts with the acid to generate hydrogen cyanide and the silyl ester which, unlike the acid, undergoes phosphine catalyzed hydrocyanation and gives the stereo-defined E-2-cyano-acrylic acids after work up.
Synthesis and Characterization of a Crown-Shaped 36-Molybdate Cluster and Application in Catalyzing Knoevenagel Condensation
He, Peipei,Kannan, Thirumurthy,Kong, Hui,Ma, Pengtao,Niu, Jingyang,Wang, Jiawei,Wang, Jingping,Xu, Baijie,Xu, Qiaofei
, (2020/07/27)
A novel crown-shaped 36-molybdate cluster with organophosphonate-functionalized polyoxomolybdates, (NH4)17Na7H12[Co(H2O)TeMo6O21{N(CH2PO3)3}]6·42H2O, has been successfully synthesized and well-characterized. It owns the highest nuclearity in the family of organophosphonate-based polyoxometalates reported so far. Furthermore, for the first time in the field, we illustrated that polyoxomolybdate could work as an effective heterogeneous catalyst for the Knoevenagel condensation reaction with high TOF (7714 h-1) and good recyclability. Impressively, the catalytic performance of 1 was also tested successfully in a large scale (～10 g) reaction, where 89percent of reaction yield and 3216 of TON were afforded.
Novel synthesis of 3-cyano-2-pyridones derivatives catalyzed by Au–Co/TiO2
Mehiaoui, Nawel,Kibou, Zahira,Berrichi, Amina,Bachir, Redouane,Choukchou-Braham, Noureddine
, p. 5263 - 5280 (2020/09/21)
Abstract: The current work described a new and highly selective method for the synthesis of substituted 3-cyano-2-pyridones scaffolds using gold-cobalt supported on TiO2 as a robust and recyclable catalyst. The products were successfully obtained by one-pot, multicomponent manner. This procedure generated the desired products 2-pyridones derivatives in good yields, from simple and available starting materials using heterogeneous and reusable catalyst. The diversity of 3-cyano-2-pyridones derivatives was prepared and characterized by IR, 1H and 13C NMR data and confirmed by element analysis data. Graphic abstract: [Figure not available: see fulltext.].
