116509-98-9Relevant academic research and scientific papers
Sodium Phenoxide Mediated Hydroxymethylation of Alkynylsilanes with N-[(Trimethylsiloxy)methyl]phthalimide
Asano, Narumi,Sasaki, Keita,Chataigner, Isabelle,Shigeno, Masanori,Kondo, Yoshinori
, p. 6926 - 6930 (2017)
The hydroxymethylation of alkynylsilanes with formaldehyde generated in situ from N-[(trimethylsiloxy)methyl]phthalimide proceeds in the presence of a stoichiometric amount of NaOPh. The reaction occurs at room temperature by using an operationally simple one-step procedure. A variety of alkynylsilanes possessing electron-donating, electron-withdrawing, and halogen groups (including heteroaryl-substituted alkynylsilanes) provide hydroxymethylated products.
Synthesis of Substituted 1-Alkylidenephthalanes via Lithium-Promoted 5-exo-dig Cyclization
Bunse, Paul,Würthwein, Ernst-Ulrich,Wünsch, Bernhard
, p. 1806 - 1812 (2018)
A one-pot synthesis of 1-alkylidenephthalanes from 3-(2-bromophenyl)propyne derivatives has been developed. 3-(2-Bromophenyl)propynal acetals 9 and corresponding orthoester 19 were treated successively with n-butyllithium and various aldehydes and ketones at low temperature to obtain 1-alkylidenephthalanes 10 and 20 with various functional groups at the exocyclic methylene moiety. Halogen-metal exchange, nucleophilic addition to various carbonyl compounds, regioselective 5-exo-dig cyclization of the respective intermediate lithium alcoholate and hydrolysis represent the key steps in this Domino reaction. A two-step mechanism involving at first a synchronous cyclization to form a vinyllithium intermediate and then a methoxide elimination leading to the respective 1-methoxy allenes is suggested based on DFT-calculations.
Oxidative cyclization of 2-allenyl-1,1′-biphenyls with α-carbonyl alkyl bromides: Facile access to functionalized phenanthrenes
Wang, Cheng-Yong,Pan, Gao-Hui,Chen, Fan,Li, Jin-Heng
, p. 4730 - 4733 (2017)
A new copper-facilitated oxidative cyclization of 2-allenyl-1,1′-biphenyls with α-carbonyl alkyl bromides for producing functionalized phenanthrenes is presented, which represents the first allene 2,3-dicarbofunctionalization triggered by oxidative radical-medicated C3-addition of the terminal allene moiety and C-Br/C-H functionalization.
Synthesis and biological activity of new arenediyne-linked isoxazolidines
Romeo, Roberto,Navarra, Michele,Giofre, Salvatore V.,Carnovale, Caterina,Cirmi, Santa,Lanza, Giuseppe,Chiacchio, Maria A.
, p. 3379 - 3385 (2014)
Arenediyne-isoxazolidine conjugates have been synthesized as a new scaffold for the development of bioactive mimics. Some of the synthesized compounds are endowed with antiproliferative activity against three human cancer cell lines. Their thermal reactiv
One-pot synthesis of 3-substituted-4H-[1,2,3] triazolo[5,1-c][1,4]oxazin-6(7H)-ones from propargyl alcohols, chloroacetyl chloride, and sodium azide
Chen, Jun-Min,Liu, Xiao-Ling,Sheng, Shou-Ri,Wei, Mei-Hong,Zhang, Xiao-Lan
, p. 482 - 485 (2020/11/30)
An efficient, one-pot synthesis of 3-substituted-4H-[1,2,3]triazolo[5,1-c][1,4]oxazin-6(7H)-ones is developed via sequential esterification, substitution, and 1,3-dipolar cycloaddition processes of various propargyl alcohols, chloroacetyl chloride, and so
Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent
Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro
supporting information, p. 1553 - 1558 (2021/02/26)
Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.
Gold(I)-Catalyzed Cascade Cyclization Reactions of Allenynes for the Synthesis of Fused Cyclopropanes and Acenaphthenes
Ikeuchi, Takaya,Inuki, Shinsuke,Oishi, Shinya,Ohno, Hiroaki
supporting information, p. 7792 - 7796 (2019/05/15)
A gold-catalyzed reaction of phenylene-tethered allenynes with benzofurans gave 1-(naphth-1-yl)cyclopropa[b]benzofuran derivatives, whereas the reaction of 1-allenyl-2-ethynyl-3-methylbenzene derivatives in the absence of benzofurans gave acenaphthenes in good yields. These results can be rationalized by nucleophilic attack of the alkyne moiety on an activated allene to form a vinyl cation intermediate.
Development of a telescoped flow process for the safe and effective generation of propargylic amines
Donnelly, Kian,Zhang, Huan,Baumann, Marcus
, (2019/11/02)
Propargylic amines are important multifunctional building blocks that are frequently exploited in the synthesis of privileged heterocyclic entities. Herein we report on a novel flow process that achieves the safe and effective on-demand synthesis of propargylic amines in a telescoped manner. This process minimizes exposure to hazardous azide intermediates and renders a streamlined route into these building blocks. The value of this approach is demonstrated by the rapid generation of a small selection of drug-like thiazolines that result from a high-yielding reaction cascade between propargylic amines with different aryl isothiocyanates.
Benzo[b]tellurophenes as a potential histone H3 lysine 9 demethylase (KDM4) inhibitor
Choi, Yong-Sung,Jeong, Jin-Hyun,Kim, Yoon-Jung,Kwon, So Hee,Lee, Dong Hoon
, (2019/12/02)
Gene expression and tumor growth can be regulated by methylation levels of lysine residues on histones, which are controlled by histone lysine demethylases (KDMs). Series of benzo[b]tellurophene and benzo[b]selenophene compounds were designed and synthesi
Metal-Free Regioselective Chloroazidation of Internal Alkynes
Huang, Bin,Liffert, Raphael,Linden, Anthony,Gademann, Karl
supporting information, p. 981 - 984 (2019/01/04)
A metal-free, room temperature protocol for the regioselective chloroazidation of internal alkynes is disclosed. The reactions of internal alkynes with trimethylsilyl azide (TMSN3) in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) afforded the corresponding chloroazidoalkenes in good yields. This reaction has good functional group tolerance and is operationally simple.
