862487-14-7Relevant articles and documents
Palladium(II)-Catalyzed C(sp2)-H Carbonylation of Sterically Hindered Amines with Carbon Monoxide
Cheng, Xiu-Fen,Wang, Tao,Li, Yan,Wu, Yun,Sheng, Jie,Wang, Rui,Li, Chao,Bian, Kang-Jie,Wang, Xi-Sheng
supporting information, p. 6530 - 6533 (2018/10/20)
A palladium-catalyzed, amine-directed C(sp2)-H carbonylation of α,α-disubstituted benzylamine under 1 atm of CO for the facile synthesis of sterically hindered benzolactam has been developed. The key to success is the use of 2,2,6,6-tetramethyl-1-piperidinyloxy as the crucial sole oxidant. The synthetic utility of this transformation has been demonstrated by the first concise synthesis of the natural product spiropachysin-20-one.
A Copper-Catalyzed Aerobic [1,3]-Nitrogen Shift through Nitrogen-Radical 4-exo-trig Cyclization
Li, Yan,Wang, Rui,Wang, Tao,Cheng, Xiu-Fen,Zhou, Xin,Fei, Fan,Wang, Xi-Sheng
supporting information, p. 15436 - 15440 (2017/11/01)
A novel radical [1,3]-nitrogen shift catalyzed by copper diacetate under an oxygen atmosphere (1 atm) has been developed for the construction of a diverse range of indole derivatives from α,α-disubstituted benzylamine. In this reaction, oxygen was used as a clean terminal oxidant, and water was produced as the only by-product. Five inert bonds were cleaved, and two C?N bonds and one C?C double bond were constructed in one pot during this transformation. This unique method demonstrated broad application protential for the late-stage modification of biologically active natural products and drugs. Mechanistic investigations indicate that a unique 4-exo-trig cyclization of an aminyl radical onto a phenyl ring is involved in the catalytic cycle.
Facile synthesis of sterically hindered and electron-deficient secondary amides from isocyanates
Sch?fer, Gabriel,Matthey, Coraline,Bode, Jeffrey W.
, p. 9173 - 9175 (2012/11/07)
The big easy: The direct coupling of Grignard reagents to isocyanates provides a facile and robust solution for the synthesis of sterically hindered and electron-deficient secondary amides. The products are obtained in high yields without the need for excess reagents or chromatographic purification. Copyright
Ti-catalyzed reactions of hindered isocyanates with alcohols
Spino, Claude,Joly, Marc-Andre,Godbout, Cedrickx,Arbour, Melissa
, p. 6118 - 6121 (2007/10/03)
Highly hindered and sensitive isocyanates react with alcohols under mild catalysis by titanium tetra-t-butoxide to give high yields of the corresponding carbamates.
Selective muscarinic antagonists. I. Synthesis and antimuscarinic properties of 4-piperidyl benzhydrylcarbamate derivatives
Naito, Ryo,Takeuchi, Makoto,Morihira, Koichiro,Hayakawa, Masahiko,Ikeda, Ken,Shibanuma, Tadao,Isomura, Yasuo
, p. 1274 - 1285 (2007/10/03)
A series of 1-substituted-4-piperidyl benzhydrylcarbamate derivatives were synthesized and evaluated for binding affinity to M1, M2 and M3 receptors, and for antimuscarinic activities. Receptor binding assays indicated that 1-benzyl-4-piperidyl benzhydrylcarbamate derivatives showed higher affinities for M1 and M3 receptors, and good selectivities for M3 over M2 receptor, than the corresponding ester analog. These results indicate that the urethane bond is a novel linker for muscarinic antagonists, and serves to lock the molecular conformation and allows the hydrophobic portion and cationic site of the molecule to bind to M1 and M3 muscarinic receptors. Among the prepared compounds, 1-(4-methylaminobenzyl)-4-piperidyl benzhydrylcarbamate monohydrochloride (18b, YM-58790) exhibited potent inhibitory activity on bladder pressure in reflexly-evoked rhythmic contraction, comparable to oxybutynin and was approximately ten times less inhibitory on oxotremorine-induced salivary secretion than oxybutynin in rats. Further evaluation of antimuscarinic effects on bradycardia and pressor in pithed rats, and on tremor in mice, demonstrated that YM-58790 can be useful for treatment of urinary urge incontinence as a bladder-selective M3 antagonist with fewer side effects.
