33844-17-6Relevant academic research and scientific papers
Synthesis of 2-substituted indoles through cyclization and demethylation of 2-alkynyldimethylanilines by ethanol
Zhao, Guangkuan,Roudaut, Christelle,Gandon, Vincent,Alami, Mouad,Provot, Olivier
supporting information, p. 4204 - 4210 (2019/08/07)
Herein, we demonstrated that 2-alkynyldimethylamines easily cyclize in EtOH according to a 5-endo-dig annulation into 2-substituted indoles without the aid of any additives or any metal catalysts to activate the triple bond. Thus, a variety of functionalized 2-styrylindoles, 2-arylindoles, 2-alkynylindoles, and 2-alkylindoles were prepared in high to excellent yields according to an environmentally friendly protocol. The mechanism has been explored to better understand this eco-friendly access to 2-substituted indoles and DFT calculations rationalized the role of the solvent in this N-annulation/dealkylation process.
Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles
Xia, Hai-Dong,Zhang, Yan-Dong,Wang, Yan-Hui,Zhang, Chi
supporting information, p. 4052 - 4056 (2018/07/15)
A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.
Design and Synthesis of Novel Nonsteroidal Phytoestrogen-based Probes as Potential Biomarker: Evaluation of Anticancer Activity and Docking Studies
Kumar, Sumit,Verma, Nishant,Zubair, Swaleha,Faisal, Syed Mohd,Kazmi, Shadab,Chakraborty, Sudipta,Owais,Ahmed, Naseem
, p. 2242 - 2257 (2017/07/25)
Two series of novel flavones and flavone-tanaproget conjugates were designed, synthesized, 125I-radiolabeled, and evaluated for their antiproliferative activity against human cancer cell lines (MCF-7, MDA-MB-231, and HeLa). They exhibited good-
Design, synthesis, molecular docking, and biological studies of novel phytoestrogen-tanaproget hybrids
Kumar, Sumit,Verma, Nishant,Kumar, Nikhil,Patel, Alok,Roy, Partha,Pruthi, Vikas,Ahmed, Naseem
supporting information, p. 460 - 474 (2016/04/05)
A diverse range of novel and highly functionalized flavonoid-based tanaproget hybrids were synthesized and evaluated in vitro for their antimicrobial and antiproliferative activities. Novel products were synthesized in good yields (81-95%) under Pd-cataly
Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Thota Jagadeshwar,Sridhar, Balasubramanian,Reddy, Maddi Sridhar
supporting information, p. 2226 - 2229 (2015/05/13)
We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C - C bond migration. (Chemical Equation Presented).
A highly effective one-pot synthesis of quinolines from 2-alkynylnitrobenzenes
Okuma, Kentaro,Ozaki, Saori,Seto, Jun-Ichi,Nagahora, Noriyoshi,Shioji, Kosei
experimental part, p. 935 - 942 (2010/09/18)
A highly effective one-pot synthesis of poly-substituted quinolines from 2-alkynylnitrobenzenes using inexpensive reagents has been developed. Reaction of 2-alkynylnitrobenzenes with Sn/HCl in EtOH resulted in the formation of 2-aminophenyl ketones and subsequently condensed in situ with ketones to form tri-substituted quinolines in 80-97% yields.
p-Toluenesulfonic acid promoted annulation of 2-alkynylanilines with activated ketones: Efficient synthesis of 4-Alkyl-2, 3-disubstituted quinolines
Peng, Changlan,Wang, Yong,Liu, Lanying,Wang, Honggen,Zhao, Jiaji,Zhu, Qiang
scheme or table, p. 818 - 822 (2010/04/02)
Reactions between readily available 2-alkynylanilines and activated ketones such as ss-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2, 3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquinolines, which are difficult to obtain by classical methods such as the Friedlaender reaction. Quinoline dimers can be prepared efficiently with alkyl or aryl linkers at C-4.
