71095-56-2Relevant academic research and scientific papers
Domino Synthesis of 3-Alkyliden-2,3-Dihydro-4-Quinolones
Raga, Esther,Escolano, Marcos,Torres, Javier,Rabasa-Alca?iz, Fernando,Sánchez-Roselló, María,del Pozo, Carlos
, p. 1102 - 1107 (2019/01/30)
The synthesis of 3-alkyliden-2,3-dihydro-4-quinolones has been accomplished in a domino fashion through a three-step sequence that comprised an initial aza-Baylis-Hillman reaction, followed by a 1,3-rearrangement and an intramolecular amination. Starting from readily available aryl vinyl ketones and N-tosyl imines, the reaction with PPh3, CsOAc and CuI in CH3CN gave rise, in good overall yields, to final 3-alkyliden-4-quinolone derivatives, valuable scaffolds in medicinal chemistry. The simultaneous addition of two bases, PPh3 and CsOAc, was found to be crucial for the success of the process. While PPh3 promoted the reversible aza-Baylis-Hillman reaction, CsOAc triggered the subsequent 1,3-rearrangement, which shifted the initial equilibrium and allowed to complete the synthetic sequence upon the addition of CuI. (Figure presented.).
Enantioselective addition of selenosulfonates to α,β-unsaturated ketones
Luo, Shilong,Zhang, Nan,Wang, Zhen,Yan, Hailong
, p. 2893 - 2901 (2018/05/03)
An organo-catalyzed enantioselective addition of selenosulfonates to α,β-unsaturated ketones was developed for the first time. With a chiral squaramide as an efficient catalyst, the desired α-selenylated ketones were obtained in a good yields with high enantioselectivity up to 89% ee, and good results could be obtained on a gram scale. The products could also be efficiently transformed into useful building blocks with a propenylic stereocenter; the strategy presented in this study may find further applications in organic synthesis.
Novel synthetic method for 7-halogen-1-indanone
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Paragraph 0031; 0032; 0033; 0034, (2018/07/07)
The invention discloses a novel synthetic method for 7-halogen-1-indanone. The reaction general formula of the method is shown in the description, wherein X is fluorine, chlorine or bromine. The method provided by the invention uses o-halogenated acetophenone as a starting raw material, an iron-catalyzed carbonyl methylenation reaction is performed to obtain a vinyl ketone, and acid-catalyzed ringclosure is performed to obtain the 7-halogen-1-indanone. The method provided by the invention has the advantages that the raw materials are simple and easy to obtain, the post-treatment is simple andthe total yield is high, and can provide an important reference for industrialized production.
Fluorine-containing three-membered ring compound, preparation method of fluorine-containing three-membered ring compound and preparation method of fluoroalkyl sulfonium salt
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Paragraph 0172; 0173; 0174; 0175; 0194; 0195, (2016/10/08)
The invention discloses a fluorine-containing three-membered ring compound shown in the formula V-a, V-b or V-c and a preparation method thereof. The preparation method comprises that in an organic solvent, fluoroalkyl sulfur ylide shown in the formula II
Diastereoselective Johnson-Corey-Chaykovsky trifluoroethylidenation
Duan, Yaya,Zhou, Bin,Lin, Jin-Hong,Xiao, Ji-Chang
supporting information, p. 13127 - 13130 (2015/08/18)
(2,2,2-Trifluoroethyl)diphenylsulfonium triflate was found to be an efficient ylide reagent for the Johnson-Corey-Chaykovsky reaction to afford trifluoromethyl epoxides, cyclopropanes and aziridines. Interestingly, excellent but different diastereoselectivity was observed for these transformations. Both trifluoromethyl epoxides and cyclopropanes were obtained with trans-selectivity, whereas aziridines were obtained with cis-selectivity.
Oxa-Michael addition promoted by the aqueous sodium carbonate
Guo, Shi-Huan,Xing, Sheng-Zhu,Mao, Shuai,Gao, Ya-Ru,Chen, Wen-Liang,Wang, Yong-Qiang
supporting information, p. 6718 - 6720 (2014/12/11)
An efficient Michael addition of alcohols to activated alkenes promoted by sodium carbonate with water as reaction medium has been developed. The reaction provides a general, economical and environmentally friendly approach for the synthesis of β-alkoxycarbonyl compounds.
Allenyl azide cycloaddition chemistry: Application to the total synthesis of (±)-meloscine
Feldman, Ken S.,Antoline, Joshua F.
, p. 934 - 937 (2012/05/05)
The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3
Highly efficient route to functionalized tetrahydrocarbazoles using a tandem cross-metathesis/intramolecular-hydroarylation sequence
An, Xiao-Lei,Chen, Jia-Rong,Li, Chang-Feng,Zhang, Fu-Gen,Zou, You-Quan,Guo, Ying-Cen,Xiao, Wen-Jing
, p. 2258 - 2265 (2011/06/11)
The scope of the novel ruthenium-catalyzed tandem cross-metathesis/ intramolecular-hydroarylation sequence is described. This methodology offers a practical and efficient synthesis of structurally diverse and complex tetrahydrocarbazoles in good to excellent yields (up to 98%). Moreover, preliminary efforts towards the development of an enantioselective version of the current process by sequential catalysis with ruthenium complex and chiral amine are presented, with high yields and enantioselectivities (up to 88% yield and 91% ee).
Palladium-catalyzed intramolecular α-arylation of aliphatic ketone, formyl, and nitro groups
Muratake, Hideaki,Natsume, Mitsutaka,Nakai, Hiroshi
, p. 11783 - 11803 (2007/10/03)
Intramolecular arylation of properly designed substrates bearing a ketone, formyl, or nitro terminating group was achieved by use of a PdCl 2(Ph3P)2-Cs2CO3 reaction system to form a variety of carbocyclic compounds. Arylation in ketone compounds afforded benzene-annulated bridged or spirocycloalkanone derivatives, depending on the structure of the cyclization precursors. Arylation in formyl compounds occurred at the α-position (α-arylation) or at the carbonyl carbon (carbonyl-arylation) depending on the structure of the cyclization precursors and on the reaction solvent. An α-arylated secondary nitro group was partially transformed to ketone in the manner of the Nef reaction, whereas a tertiary nitro group was partially eliminated to afford a styrene-type olefin. Graphical Abstract
