42925-43-9Relevant academic research and scientific papers
Bi(OTf)3-Catalyzed Alkyl-Intercepted Meyer-Schuster Rearrangement of Propargylic Alcohols for the Synthesis of 1,2,3,5-Tetrasubstituted Pentane-1,5-diones
Wang, Zhihai,Sun, Yuxing,Zhang, Qinglin,Pan, Wanyong,Li, Tiantian,Yin, Yan
, p. 3329 - 3340 (2022/02/25)
An alkyl intercepted Meyer-Schuster rearrangement reaction with α,β-unsaturated ketones as the electrophiles was first investigated, which provided a facile method to construct 2-methylene-pentane-1,5-diones. Then the in situ generated 2-methylene-pentane-1,5-diones underwent a Michael addition to give diverse 2-malononitrile methyl substituted pentane-1,5-diones in a one-pot fashion. This transformation was reliable on a gram scale. The high yield, convenient experimental operation, and 100% atom economy made it a valuable method for the construction of 1,2,3,5-tetrasubstituted pentane-1,5-dione derivatives.
Method for preparing phenyl propenone compound by catalyzing phenylacetylene through molecular sieve
-
Paragraph 0076-0080, (2021/03/13)
The invention belongs to the field of molecular sieve catalysis and organic synthesis, and discloses a method for preparing a phenyl propenone compound by catalyzing phenylacetylene through a molecular sieve, which comprises the following steps: adding a phenylacetylene compound I, aldehyde II and a molecular sieve catalyst into a small reaction kettle without adding an organic solvent and any other assistants; performing stirring to react for 0.25-6 hours under the condition of heating at 30-90 DEG C, cooling the reaction kettle to room temperature, performing diluting with ethyl acetate, andcentrifugally separating the catalyst to obtain the phenyl allyl ketone compound III. The molecular sieve catalyst provided by the invention is H-beta of which the silica-alumina ratios are respectively 14 and 29. The method is simple in reaction process, high in catalytic activity and selectivity, recyclable, environmentally friendly and capable of achieving large-scale industrial production.
Enantioselective Conjugate Azidation of α,β-Unsaturated Ketones under Bifunctional Organocatalysis by Direct Activation of TMSN3
Humbrías-Martín, Jorge,Pérez-Aguilar, M. Carmen,Mas-Ballesté, Rubén,Dentoni Litta, Antonella,Lattanzi, Alessandra,Della Sala, Giorgio,Fernández-Salas, Jose A.,Alemán, José
, p. 4790 - 4796 (2019/09/16)
An enantioselective organocatalytic conjugate azidation of α,β-unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN3, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre-formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst. (Figure presented.).
Efficient catalytic performance of calcined tungstophosphoric acid for the Claisen-Schmidt condensation under solvent-free reaction
Alharthi, Abdulrahman I.
, p. 2579 - 2584 (2019/10/02)
Effect of calcination of tungstophosphoric acid catalyst was evaluated in terms of the synthesis of chalcone derivatives via Claisen-Schmidt condensation using the reaction of acetophenone and several substituted aldehydes. The catalyst was characterized before and after calcination by FT-IR to assess the effectiveness of the synthesis of the desired products. The calcined tungstophosphoric acid catalyst (HPW-CL) showed a better performance and high yield of Claisen-Schmidt products in a short period of time. It was also found out that the calcined tungstophosphoric acid provides a chemo selective, efficient and environmentally benign synthesis of chalcone in an excellent yield in a solvent-free system.
Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
supporting information, p. 2003 - 2006 (2018/04/16)
A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p
Imidazole-triazine type compound and preparation method and application thereof
-
Paragraph 0031; 0032; 0033; 0034; 0035; 0037, (2017/10/06)
The invention provides an imidazole-triazine type compound which is shown as the formula 3 in the description and a preparation method and application thereof. The method comprises the steps that a triazine compound and an alpha,beta-unsaturated ketone type compound are mixed and added into a solvent, under the existence of a metal copper catalyst and an oxidizing material, the mixed solution is stirred and reacts 5-20 hours under the temperature of 60-150 DEG C, after the reaction is finished, the reacted solution is subjected to post processing, and the imidazole-triazine type compound which is shown as the formula 3 is obtained; the metal copper catalyst is halogenide of the copper or a copper salt; the oxidizing material is a halogen elementary substance. The imidazole-triazine type compound can be applied to prepare antibacterial drugs or antibacterial agents, and the preferred antibacterial drugs are the drugs which inhibit activity of escherichia coli.
A convenient synthesis of 4-alkyl-3-benzoylpyrroles from α,β-unsaturated ketones and tosylmethyl isocyanide
Kumar, Kapil,More, Shital S.,Goyal, Sandeep,Gangar, Mukesh,Khatik, Gopal L.,Rawal, Ravindra K.,Nair, Vipin A.
supporting information, p. 2315 - 2319 (2016/05/10)
A convenient synthesis of 4-alkyl-3-benzoyl pyrrole was achieved from α,β-unsaturated ketones and tosylmethyl isocyanide in the presence of mild base LiOH·H2O. This method is very economical and was successfully utilized for the synthesis of various 4-alkyl-3-benzoylpyrrole derivatives with good to excellent yields.
Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols
Pennell, Matthew N.,Kyle, Michael P.,Gibson, Samantha M.,Male, Louise,Turner, Peter G.,Grainger, Richard S.,Sheppard, Tom D.
supporting information, p. 1519 - 1525 (2016/05/19)
The regioselective gold-catalysed hydration of propargylic alcohols to β-hydroxy ketones can be achieved by diverting the gold-catalysed Meyer-Schuster rearrangement through the addition of a protic additive with a pKa of 7-9 such as p-nitrophe
Triazole-gold promoted intermolecular propargyl alcohol addition to alkyne: the reaction cascade toward substituted allenes
Hosseyni, Seyedmorteza,Ding, Shengtao,Su, Yijin,Akhmedov, Novruz G.,Shi, Xiaodong
supporting information, p. 296 - 299 (2016/01/09)
Gold-catalyzed intermolecular propargyl alcohol addition to alkyne was achieved. The reaction of propargyl alcohol with a typical gold catalyst gave the hydration product almost exclusively. The triazole gold catalyst (TA-Au) successfully prevented the hydration, giving the vinyl ether followed by a 3,3-rearrangement. Synthetically useful substituted allenes were formed with high efficiency, substrate tolerability and chemoselectivity. Also, more than 95% chirality transfer from propargyl alcohol to allene was obtained.
Co-N-C Catalyst for C-C Coupling Reactions: On the Catalytic Performance and Active Sites
Zhang, Leilei,Wang, Aiqin,Wang, Wentao,Huang, Yanqiang,Liu, Xiaoyan,Miao, Shu,Liu, Jingyue,Zhang, Tao
, p. 6563 - 6572 (2015/11/18)
C-C bond-forming reactions are important in chemistry for construction of complex large molecules from readily available simple substrates. However, they usually involve the employment of organic halides and suffer from toxic or environmental issues. We report an efficient and environmentally benign methodology-aerobic oxidative cross-coupling of primary and secondary alcohols-to directly produce α,β-unsaturated ketones that are key intermediates for synthesis of agrochemical, pharmaceutical, and other fine chemicals. A noble-metal-free Co-N-C catalyst, derived from pyrolysis of cobalt-phenanthroline complexes on a mesoporous carbon support, is developed toward the target reactions and shows high catalytic activity (turnover frequency of 3.8 s-1 based on Co single atoms, surpassing the state of art in the literature), good recyclability, and wide applicability to diverse substrates (28 examples). The active sites in the Co-N-C catalyst are proposed to be Co single atoms bonded with N within graphitic sheets.
