78450-85-8Relevant academic research and scientific papers
Effect of Transition Metals on Chemodivergent Cross-Coupling of Acrylamides with Vinyl Acetate via C-H Activation
Logeswaran, Ravichandran,Jeganmohan, Masilamani
supporting information, p. 5679 - 5683 (2021/08/03)
A novel chemodivergent cross-coupling of acrylamides and vinyl acetates has been realized via metal-catalyzed vinylic C-H activation. The selective olefinic C-H vinylation and alkenylation reaction was examined with a variety of differently functionalized acrylamides. The reaction efficiently generates a range of highly synthetically valuable butadienes with good functional group tolerance in good to moderate yields. A possible catalytic reaction mechanism involving the chelation-assisted olefinic C-H activation via an acetate-assisted deprotonation pathway is proposed.
Enantioselective Construction of Quaternary All-Carbon Centers via Copper-Catalyzed Arylation of Tertiary Carbon-Centered Radicals
Wu, Lianqian,Wang, Fei,Chen, Pinhong,Liu, Guosheng
supporting information, p. 1887 - 1892 (2019/02/05)
An enantioselective copper-catalyzed arylation of tertiary carbon-centered radicals, leading to quaternary all-carbon stereocenters, has been developed herein. The tertiary carbon-centered radicals, including both benzylic and nonbenzylic radicals, were produced by the addition of trifluoromethyl radical to α-substituted acrylamides, and subsequently captured by chiral aryl copper(II) species to give C-Ar bonds with excellent enantioselectivity. Importantly, an acylamidyl (CONHAr) group adjacent to the tertiary carbon radical is essential for the asymmetric radical coupling. The reaction itself features broad substrate scope, excellent functional group compatibility and mild conditions.
Design, synthesis, and in vivo SAR of a novel series of pyrazolines as potent selective androgen receptor modulators
Zhang, Xuqing,Li, Xiaojie,Allan, George F.,Sbriscia, Tifanie,Linton, Olivia,Lundeen, Scott G.,Sui, Zhihua
, p. 3857 - 3869 (2008/02/10)
A novel series of pyrazolines 2 have been designed, synthesized, and evaluated by in vivo screening as tissue-selective androgen receptor modulators (SARMs). Structure-activity relationships (SAR) were investigated at the R 1 to R6 positions as well as the core pyrazoline ring and the anilide linker. Overall, strong electron-withdrawing groups at the R 1 and R2 positions and a small group at the R5 and R6 position are optimal for AR agonist activity. The (S)-isomer of 7c exhibits more potent AR agonist activity than the corresponding (R)-isomer. (S)-7c exhibited an overall partial androgenic effect but full anabolic effect via oral administration in castrated rats. It demonstrated a noticeable antiandrogenic effect on prostate in intact rats with endogenous testosterone. Thus, (S)-7c is a tissue-selective nonsteroidal androgen receptor modulator with agonist activity on muscle and mixed agonist and antagonist activity on prostate.
Synthesis of α-alkylacrylic esters
Marshalok, G.A.,Yatchishin, I. I.,Tolopko, D. K.
, p. 603 - 608 (2007/10/02)
By the reaction of α-alkylacryloyl chlorides with alcohols the esters of the acids were synthesized.The kinetic parameters of the process were determined.It was shown that an appreciable change in the reaction rate constant is only observed in the transition from acryloyl chloride to methacryloyl chloride and with substitution of methanol by ethanol.A method was developed for the production of methyl α-alkylacrylates by the reaction of the acids with alcohols in the presence of thionyl chloride without previous isolation of the corresponding acid chlorides.
Photochemistry of Aliphatic Imides. Synthesis of Azetidine-2,4-diones via Photochemical Isomerization of Succinimides and N-Formyl-N-methyl α, β -Unsaturated Amides
Maruyama, Kazuhiro,Ishitoku, Takeshi,Kubo, Yasuo
, p. 27 - 34 (2007/10/02)
Photochemical reactions of alkyl-substituted succinimides and N-formyl-N-methyl α, β -unsaturated amides were studied.Photolysis of succinimide 1 gave azetidine-2,4-dione 2 together with a small amount of 3.The photoinduced ring-contraction reaction is explained in terms of a two-photon mechanism.Similarly, several other succinimide derivates photochemically gave the corresponding azetidine-2,4-diones.In addition, the photochemical cyclization of 3 to 2 was extended to the synthesis of azetidine-2,4-diones from N-formyl-N-methyl α, β -unsaturated amides.
