129812-23-3Relevant academic research and scientific papers
One-step regioselective synthesis of benzofurans from phenols and α-Haloketones
Wang, Bingqiao,Zhang, Qiu,Luo, Juan,Gan, Zongjie,Jiang, Wengao,Tang, Qiang
, (2019)
Reported here is the direct synthesis of naphthofurans and benzofurans from readily available phenols and α-haloketones promoted by titanium tetrachloride which combines Friedel-Crafts-like alkylation and intramolecular cyclodehydration into one step. This simple protocol allows for the formation of a variety of high value naphthofurans and benzofurans within which a series of cyclic and acyclic groups are readily incorporated. This process demonstrates the advantages of high levels of regioselectivity, broad substrate scope, and moderate to excellent yields.
Titanium tetrachloride promoted cyclodehydration of aryloxyketones: Facile synthesis of benzofurans and naphthofurans with high regioselectivity
Zhang, Qiu,Luo, Juan,Wang, Bingqiao,Xiao, Xiaoqin,Gan, Zongjie,Tang, Qiang
supporting information, p. 1337 - 1340 (2019/04/16)
An efficient and facile method for the synthesis of a broad series of benzofurans and naphthofurans is described. The direct intramolecular cyclodehydration of aryloxyketones in the presence of titanium tetrachloride affords the corresponding benzofurans and naphthofurans with good regioselectivity and yields.
Method for synthesizing naphthofuran derivative by taking titanium tetrachloride as dehydrating agent
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Paragraph 0032-0035, (2019/04/17)
The invention discloses a method for preparing a naphthofuran derivative by taking naphthoxy ketone as a raw material through dehydrating cyclization under the action of titanium tetrachloride. Namely, under protection of inert gas, alpha-naphthoxy ketone
Preparation method of naphthofuran derivative
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Paragraph 0040-0043, (2019/04/17)
The invention discloses a method for efficiently synthesizing a naphthofuran derivative from naphthol and an alpha-haloketone under the action of titanium tetrachloride by one step. The method specifically includes adding the naphthol and polyfluoroalcoho
Br?nsted Acid Catalyzed Functionalization of Aromatic Alcohols through Nucleophilic Substitution of Hydroxyl Group
Mishra, Abhishek Kumar,Biswas, Srijit
, p. 2355 - 2363 (2016/04/04)
The hydroxyl groups of naphthol and tautomerizable phenol derivatives have been substituted by O-, S-, N-, and C-centered nucleophiles under solvent-free reaction conditions. The products are generated in good to excellent yields. para-Toluenesulfonic acid exhibits the best catalytic activity compared to other Bronsted acids. Experimental observations suggest that the reaction proceeds through the intermediacy of the keto tautomer of naphthol. Nucleophilic addition to the carbonyl group followed by elimination of water generates the desired product. The present methodology provides access to substituted naphtho[2,1-b]furan derivatives. The products generated using N-centered nucleophiles can be further transformed to important classes of organic molecules such as benzocarbazole and imidazole derivatives.
Synthesis and phototransformations of novel styryl-substituted furo-benzobicyclo[3.2.1]octadiene derivatives
Kika?, Ilijana,?kori?, Irena,Marini?, ?eljko,?indler-Kulyk, Marija
experimental part, p. 9405 - 9414 (2011/02/21)
Novel cis- and trans-(o-H/Me/vinyl) substituted styryl furo-benzobicyclo[3. 2.1]octadiene derivatives (7a,b, 8) were prepared and transformed to the novel naphthofuran derivatives of benzobicyclo[3.2.1]octadiene (6a,b) and novel phenanthrene-benzobicyclo[
Furocoumarin-, Naphthofuran-, and Furoquinoline-Annulated 1,2-Dioxetanes: Synthesis, Thermolysis. and Mutagenicity
Adam, Waldemar,Hauer, Hermann,Mosandl, Thomas,Saha-Moeller, Chantu R.,Wagner, Willi,Wild, Dieter
, p. 1227 - 1236 (2007/10/02)
The low temperature photooxygenation of the furocoumarins 1a-e, the naphthofurans 1f-h, and the furoquinoline 1i afforded the corresponding dioxetanes 2 in good yields, except the linearly annulated napthofuran 1f, which led exclusively to the allylic hydroperoxide 5f by ene reaction with singlet oxygen.The dioxetanes 2 were rigorously purified by means of low temperature silicagel chromatography and fully characterized.Thermolysis of the furocoumarin dioxetanes 2a-e led to the expected cleavage products 3a-e (acetyloxy- and acetyl-substituted coumarins), while the naphtho- and quinolinofuran dioxetanes 2g-i gave in addition to the cleavage products 3g-i also the spiroepoxides 4g-i.Intramolecular electron transfer from the aromatic moiety to the dioxetane ring, with subsequent cyclization of the radical-ion species and fragmentation is postulated as mechanism for the formation of this novel rearrangement product of dioxetanes.On heating in chloroform the spiroepoxides 4g,h rearranged into the 1,4-dioxole 6g, but heating of 4g in methanol gave the dioxine 7g by trapping of the dipolar intermeadiate. - The furocoumarin dioxetanes 2a,c,d showed high mutagenic activity in the Salmonella typhimurium strain TA 100 but not in the strain TA 2638.The naphtho- and quinolinofuran dioxetanes 2h,i and the spiroepoxides 4g,h were nonmutagenic in the TA 100 strain.Epoxide-like DNA damage appears to be responsible for mutagenicity of the furocoumarin dioxetanes 2a,c,d.
