33143-89-4Relevant academic research and scientific papers
Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes
Cervi, Aymeric,Vo, Yen,Chai, Christina L. L.,Banwell, Martin G.,Lan, Ping,Willis, Anthony C.
, p. 178 - 198 (2020/12/22)
Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.
Copper-catalyzed intramolecular carbotrifluoromethylation of alkynes for the construction of trifluoromethylated heterocycles
Wang, Yanan,Jiang, Min,Liu, Jin-Tao
supporting information, p. 15315 - 15319 (2016/02/18)
A mild and efficient copper-catalyzed intramolecular carbotrifluoromethylation of alkynes has been achieved in the presence of Togni reagent as trifluoromethylating reagent. The reaction tolerates a range of substrates to give a group of trifluoromethylated heterocycles with high selectivities. A plausible mechanism was proposed on the basis of experimental results. And the Togni award goes to Copper-catalyzed intramolecular carbotrifluoromethylation of alkynes is carried out with a Togni reagent as the trifluoromethylating reagent (see scheme). Various trifluoromethylated heterocycles are synthesized in moderate to good yields. Moreover, a range of common functional groups is tolerated under the reaction conditions.
Semi-synthesis and biological evaluation of 1,2,3-triazole-based podophyllotoxin congeners as potent antitumor agents inducing apoptosis in HepG2 cells
Chen, Jinying,Ma, Liang,Zhang, Ronghong,Tang, Jie,Lai, Huijun,Wang, Jun,Wang, Guangcheng,Xu, Qinyuan,Chen, Tao,Peng, Fei,Qiu, Jingxiang,Liang, Xiaolin,Cao, Dong,Ran, Yan,Peng, Aihua,Wei, Yuquan,Chen, Lijuan
, p. 945 - 956 (2013/02/22)
A series of 4β-[(4-substituted)-1,2,3-triazol-1-yl]podophyllotoxin congeners were synthesized by employing click chemistry and further evaluated for their antitumor activity by MTT assay. Among them, six congeners (10, 11, 12, 13, 22, and 24) exhibited ap
Gold nanoparticles supported on TiO2 catalyse the cycloisomerisation/oxidative dimerisation of aryl propargyl ethers
Efe, Christina,Lykakis, Ioannis N.,Stratakis, Manolis
supporting information; experimental part, p. 803 - 805 (2011/04/12)
Gold nanoparticles supported on TiO2 (～1%) catalyse in high yields the selective cycloisomerisation of aryl propargyl ethers into the corresponding 2H-chromenes, under heterogeneous conditions. 2H,2′H-3, 3′-Bichromenes resulting from a catalytic oxidative dimerization pathway are also formed as by-products. The Royal Society of Chemistry 2011.
Ph3PAuNTf2 as a superior catalyst for the selective synthesis of 2H-chromenes: Application to the concise synthesis of benzopyran natural products
Lykakis, Ioannis N.,Efe, Christina,Gryparis, Charis,Stratakis, Manolis
supporting information; experimental part, p. 2334 - 2338 (2011/06/20)
Ph3PAuNTf2 (≈1 mol-%) catalyzes the selective cycloisomerization of substituted aryl propargyl ethers into 2H-chromenes in excellent yields. Benzofuran byproducts are formed only in the case of electron-deficient arenes, in up to 7% relative yield. The Ph 3PAuNTf2-catalyzed cyclization of aryl propargyl ethers was applied as a key step to the concise synthesis of the naturally occurring benzopyrans seselin, xanthyletin, precocenes I and II, 8-(3′,3′- dimethylallyl)wenteria chromene, and 2,2-dimethyl-8-prenylchromene-6-propenoic acid. Ph3PAuNTf2 is a general, highly efficient, and product-selective catalyst for the clean synthesis of 2H-chromenes from the cycloisomerization of aryl propargyl ethers.The Ph3PAuNTf 2-catalyzed cyclization was applied as a key step in the synthesis of several benzopyran-bearing naturally occurring substances. Copyright
Copper(I) iodide: A catalyst for the improved synthesis of aryl propargyl ethers
Bell,Davies,Geen,Mann
, p. 707 - 712 (2007/10/02)
Copper(I) iodide catalyses the reaction between phenols and dialkylpropargyl chlorides to give aryl 1,1-dialkylpropargyl ethers 5 a-k and 7a-e in good yields and purity. These ethers are important as precursors to the 2H-1-benzopyrans 8a-l and 9a-e.
Improved Synthesis of Aryl 1,1-Dimethylpropargyl Ethers
Godfrey, Jollie D.,Mueller, Richard H.,Sedergran, Thomas C.,Soundarajan, Nachimuthu,Colandrea, Vincent J.
, p. 6405 - 6408 (2007/10/02)
An efficient, general, and practical synthesis of aryl 1,1-dimethylpropargyl ethers has been developed.
