1859-75-2Relevant academic research and scientific papers
Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes
Fan, Pei,Lan, Yun,Zhang, Chang,Wang, Chuan
, p. 2180 - 2186 (2020/03/03)
An unprecedented asymmetric acyl-carbamoylation of pendant alkenes tethered on aryl carbamic chlorides with both aliphatic and aromatic aldehydes has been developed via the cooperative catalysis of a chiral nickel-PHOX complex and tetrabutylammonium decatungstate. This reaction represents the first example of merging hydrogen-atom-transfer photochemistry and asymmetric transition metal catalysis in difunctionalization of alkenes. Using this protocol, a variety of oxindoles bearing a challenging quaternary stereogenic center are furnished under mild conditions in highly enantioselective manner.
Site-Selective Linear Alkylation of Anilides by Cooperative Nickel/Aluminum Catalysis
Okumura, Shogo,Komine, Takuya,Shigeki, Erika,Semba, Kazuhiko,Nakao, Yoshiaki
supporting information, p. 929 - 932 (2017/12/26)
We report meta- and para-selective linear alkylation reactions of anilides with alkenes by nickel/N-heterocyclic carbene (NHC) and aluminum catalysis. With a less bulky NHC, the alkylation reaction of N-methyl-N-phenylcyclohexanecarboxamides proceeded mainly at the meta position. In contrast, a bulky NHC ligand led to the para-selective alkylation of N-sec-alkyl anilides.
C–C bond-forming reactions of ground-state aryl halides under reductive activation
Emery, Katie J.,Tuttle, Tell,Kennedy, Alan R.,Murphy, John A.
, p. 7875 - 7887 (2016/11/17)
Under basic conditions aryl halides can undergo SRN1 reactions, BHAS reactions and benzyne formations. Appropriate complex substrates afford an opportunity to study inherent selectivities. SRN1 reactions are usually favoured under ph
Visible-light-mediated reaction: Synthesis of quinazolinones from 1,2-dihydroquinazoline 3-oxides
Wu, Chun-Ku,Yang, Ding-Yah
, p. 65988 - 65994 (2016/07/26)
1-Methyl-2-phenylquinazolin-4(1H)-ones were synthesized in good yield by exposing 1,4-dimethyl-2-phenyl-1,2-dihydroquinazoline 3-oxides or 1-methyl-2-phenyl-1,2-dihydroquinazoline 3-oxides to visible light in acetonitrile in the absence of any external ph
Silica gel-mediated hydroamination/semipinacol rearrangement of 2-alkylaminophenylprop-1-yn-3-ols: Synthesis of 2-oxindoles from alkynes and 1-(2-aminophenyl) ketones
Susanti, Dewi,Ng, Linda Li Ru,Chan, Philip Wai Hong
supporting information, p. 353 - 358 (2014/05/20)
2-Alkylaminophenylprop-1-yn-3-ols, prepared from the lithium diisopropylamide (LDA)- mediated 1,2-addition of alkynes to 1-(2-aminophenyl) ketones, can be converted to 3,3-disubstituted 2-oxindoles by using silica gel in n-hexane/ ethyl acetate (20:1 v/v) as the reaction medium. The utility of the approach as a potential scale-up strategy for the synthesis of 2-oxindoles was exemplified by the large-scale synthesis of one adduct in excellent yield. The synthetic applicability of this chemistry was also demonstrated by the recycling of the silica gel up to 8 times with no apparent loss of activity being observed for the same example.
Copper-catalyzed intramolecular oxidative C(sp3)-H amidation of 2-aminoacetophenones: Efficient synthesis of indoline-2,3-diones
Huang, Jinbo,Mao, Tingting,Zhu, Qiang
supporting information, p. 2878 - 2882 (2014/05/20)
An efficient synthesis of diverse indoline-2,3-diones from 2-aminoacetophenones through copper-catalyzed intramolecular C(sp3)-H amidation is developed. The reaction proceeds in DMSO by using O2 as the sole oxidant to provide the desired products in moderate to good yields.
Asymmetric synthesis of 1,3-diamines. II: Diastereoselective reduction of atropisomeric N-tert -butanesulfinylketimines
Martjuga, Marina,Belyakov, Sergey,Liepinsh, Edvards,Suna, Edgars
experimental part, p. 2635 - 2647 (2011/06/20)
Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for at
Evolution from a natural flavones nucleus to obtain 2-(4-propoxyphenyl) quinoline derivatives as potent inhibitors of the S. aureus NorA efflux pump
Sabatini, Stefano,Gosetto, Francesca,Manfroni, Giuseppe,Tabarrini, Oriana,Kaatz, Glenn W.,Patel, Diixa,Cecchetti, Violetta
experimental part, p. 5722 - 5736 (2011/10/09)
Overexpression of efflux pumps is an important mechanism by which bacteria evade the effects of substrate antimicrobial agents. Inhibition of such pumps is a promising strategy to circumvent this resistance mechanism. NorA is a Staphylococcus aureus efflux pump that confers reduced susceptibility to many structurally unrelated agents, including fluoroquinolones, resulting in a multidrug resistant phenotype. In this work, a series of 2-phenyl-4(1H)- quinolone and 2-phenyl-4-hydroxyquinoline derivatives, obtained by modifying the flavone nucleus of known efflux pump inhibitors (EPIs), were synthesized in an effort to identify more potent S. aureus NorA EPIs. The 2-phenyl-4- hydroxyquinoline derivatives 28f and 29f display potent EPI activity against SA-1199B, a strain that overexpresses norA, in an ethidium bromide efflux inhibition assay. The same compounds, in combination with ciprofloxacin, were able to completely restore its antibacterial activity against both S. aureus SA-K2378 and SA-1199B, norA-overexpressing strains.
A practical, metal-free synthesis of 1H-Lndazoles
Counceller, Carla M.,Eichman, Chad C.,Wray, Brertda C.,Stambuli, James P.
supporting information; experimental part, p. 1021 - 1023 (2009/04/07)
The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0-23 °C and is amenable to scale-up. The synthesis of 1 H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.
Regioselective synthesis of silylated pyrazolines and indazolines by reaction of pyrazolium and indazolium salts with silyllithium reagents
Gonzalez-Nogal, Ana M.,Calle, Mariola,Calvo, Luis A.,Cuadrado, Purificacion,Gonzalez-Ortega, Alfonso
, p. 4663 - 4669 (2007/10/03)
Pyrazolium salts react with dimethylphenylsilyl- and tert- butyldiphenylsilyllithium to give, in general, only one of the two possible 5-silyl-3-pyrazolines. On the other hand, indazolium and isoindazolium salts lead to 3-silylindazolines and occasionally
