3226-15-1Relevant academic research and scientific papers
Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans
Yu, Xiaoye,Meng, Qing-Yuan,Daniliuc, Constantin G.,Studer, Armido
, p. 7072 - 7079 (2022/04/12)
The 2,3-dihydrobenzofuran scaffold is widely found in natural products and biologically active compounds. Herein, dearomatizing 2,3-fluoroaroylation of benzofurans with aroyl fluorides as bifunctional reagents to access 2,3-difunctionalized dihydrobenzofurans is reported. The reaction that occurs by cooperative NHC/photoredox catalysis provides 3-aroyl-2-fluoro-2,3-dihydrobenzofurans with moderate to good yield and high diastereoselectivity. Cascades proceed via radical/radical cross-coupling of a benzofuran radical cation generated in the photoredox catalysis cycle with a neutral ketyl radical formed through the NHC catalysis cycle. The redox-neutral transformation exhibits broad substrate scope and high functional group compatibility. With anhydrides as bifunctional reagents, dearomatizing aroyloxyacylation of benzofurans is achieved and the strategy can also be applied to N-acylated indoles to afford 3-aroyl-2-fluoro-dihydroindoles.
Asymmetric synthesis of 3-benzofuranones through 5-exo-trig cyclization of 4-nitroaryl olefins
Verma, Nishant,Kumar, Sumit,Ahmed, Naseem
supporting information, p. 3547 - 3550 (2016/07/18)
Organo-catalyzed aldol condensation of 2-hydroxyacetophenone and 4-nitrobenzaldehyde underwent regio- and enantioselective cyclization via intramolecular 5-exo-trigonal cyclization to give 4-nitroaryl-3-benzofuranones. The product formation indicated that
Piperidine-mediated annulation of 2-acylphenols with 4-nitrobenzaldehyde to 3-benzofuranones
Verma, Nishant,Kundi, Varun,Ahmed, Naseem
supporting information, p. 4175 - 4179 (2015/06/22)
Piperidine - mediated reactions of 2-acylphenols and 4-nitrobenzaldehydes afforded 3-benzofuranones in high yield (82-95%) at reflux temperature in ethanol. The electron density calculation of HOMO-LUMO energy in the chalcone intermediates by DFT showed t
Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone
Lo, Hong-Jay,Lin, Chin-Yin,Tseng, Mei-Chun,Chein, Rong-Jie
supporting information, p. 9026 - 9029 (2014/09/17)
A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.
TMSOTf-promoted addition of alkynes to aldehydes: A novel synthesis of chroman-4-ones
Ji, Yeon Park,Ullapu, Punna Reddy,Choo, Hyunah,Jae, Kyun Lee,Min, Sun-Joon,Ae, Nim Pae,Kim, Youseung,Baek, Du-Jong,Yong, Seo Cho
experimental part, p. 5461 - 5469 (2009/05/07)
A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Facile synthesis of 2,2′-dialkylated 4,4′-oxybiphenols
Maeyama, Katsuya,Fujiwara, Yasushi,Nishimuro, Makiya,Yoshida, Yasuhiko,Yonezawa, Noriyuki
, p. 603 - 609 (2007/10/03)
2,2′-Alkyl-disubstituted 4,4′-oxybiphenols (4) were prepared in good yields through esterification of 4,4′-oxybiphenol (1), AlCl 3-promoted Fries rearrangement, and AlCl3/NaBH 4-promoted reduction reaction. Copyright Taylo
Targeting the gatekeeper residue in phosphoinositide 3-kinases
Alaimo, Peter J.,Knight, Zachary A.,Shokat, Kevan M.
, p. 2825 - 2836 (2007/10/03)
A single residue in the ATP binding pocket of protein kinases-termed the gatekeeper-has been shown to control sensitivity to a wide range of small molecule inhibitors (Chem. Biol. 2004, 11, 691; Chem. Biol. 1999, 6, 671). Kinases that possess a small side chain at this position (Thr, Ala, or Gly) are readily targeted by structurally diverse classes of inhibitors, whereas kinases that possess a larger residue at this position are broadly resistant. Recently, lipid kinases of the phosphoinositide 3-kinase (PI3-K) family have become the focus of intense research interest as potential drug targets (Chem. Biol. 2003, 10, 207; Curr. Opin. Pharmacol. 2003, 3, 426). In this study, we identify the residue that corresponds structurally to the gatekeeper in PI3-Ks, and explore its importance in controlling enzyme activity and small molecule sensitivity. Isoleucine 848 of p110α was mutated to alanine and glycine, but the mutated kinase was found to have severely impaired enzymatic activity. A structural bioinformatic comparison of this kinase with its yeast orthologs identified second site mutations that rescued the enzymatic activity of the I848A kinase. To probe the dimensions of the gatekeeper pocket, a focused panel of analogs of the PI3-K inhibitor LY294002 was synthesized and its activity against gatekeeper mutated and wild-type p110α was assessed.
Non-metallocene compounds, method for the production thereof and use of the same for the polymerisation of olefins
-
, (2008/06/13)
The invention relates to a method for producing special transition metal compounds, to novel transition metal compounds and to the use of the same for the polymerisation of olefins.
Alkylation of dianions derived from 2-(1-iminoalkyl) phenols: Synthesis of functionalized 2-acyl phenols
Cimarelli, Cristina,Palmieri, Gianni
, p. 15711 - 15720 (2007/10/03)
A method has been developed for the almost exclusive C-alkylation of the 2-(l-liminoalkyl) phenols 1, important organic compounds with a range of employment, which allows the preparation of complex derivatives 4 with good yields starting from easily available materials. The operational simplicity of this method take advantages in providing a variety of alkylated 2-acyl phenols 5 by an easy hydrolysis of the 2-(1-iminoalkyl) phenols 4.
Study of bonding characteristics of some new metal complexes of salicylaldoxime (SALO) and its derivatives by far infrared and UV spectroscopy
Ramesh,Umasundari,Das, Kalyan K.
, p. 285 - 297 (2007/10/03)
New metal chelates of copper, lead and zinc with salicylaldoxime (SALO) and its derivatives have been prepared. The chelates have been characterized by elemental analysis, atomic absorption, infrared and UV spectroscopy. SALO behaves as a bidentate ligand forming neutral metal chelates through the phenolic oxygen and the oxime nitrogen. The M-O stretching frequencies for the transition metals show good agreement with the Irving-William's stability order Cu > Zn > Pb. Similar trend is seen for the M-N stretching frequencies in IR and the shift in transitions from UV spectral data for the metal chelates.
