153958-45-3Relevant academic research and scientific papers
Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones
Chen, Peng-Hao,Sieber, Joshua,Senanayake, Chris H.,Dong, Guangbin
, p. 5440 - 5445 (2015/09/28)
Here we report a reagent-free rhodium-catalyzed ring-expansion reaction via C-C cleavage of cyclobutenones. A variety of poly-substituted cyclopentenones and 1-indanones can be synthesized from simple cyclobutenones and benzocyclobutenones. The reaction condition is near pH neutral without additional oxidants or reductants. The potential for developing a dynamic kinetic asymmetric transformation of this reaction has also been demonstrated. Further study supports the proposed pathway involving Rh-insertion into the cyclobutenone C-C bond, followed by β-hydrogen elimination, olefin insertion and reductive elimination.
Catalytic intermolecular Pauson-Khand-type reaction: Strong directing effect of pyridylsilyl and pyrimidylsilyl groups and isolation of Ru complexes relevant to catalytic reaction
Itami, Kenichiro,Mitsudo, Koichi,Fujita, Kazuyoshi,Ohashi, Youichi,Yoshida, Jun-Ichi
, p. 11058 - 11066 (2007/10/03)
Some circumstantial evidence for the directing effect of the 2-pyhdylsilyl group in the Ru-catalyzed intermolecular Pauson-Khand-type reaction (PKR) of alkenyl(2-pyridyl)silane, alkyne, and carbon monoxide has been provided. Most importantly, we have succeeded in isolating several monometallic Ru complexes relevant to the catalytic reaction: Ru(vinylsilane)(CO)3 complexes and ruthenacyclopentene. While the stoichimetric reaction of the Ru(vinylsilane)(CO)3 complex with an alkyne led to the formation of the corresponding cyclopentenone (PKR product) at 100 °C, the ruthenacyclopentene intermediate was quantitatively produced at 50 °C. This complex was also converted to a cyclopentenone upon heating at 100 °C. Moreover, it was also found that the Ru(vinylsilane)(CO)3 complex and ruthenacyclopentene serve as catalysts in intermolecular PKR.
Agents for the treatment of overactive detrusor. VII. Synthesis and pharmacological properties of 2,3- and 3,4-diphenylcyclopentylamines, 2,3-diphenyl-2-cyclopentylamines, and related compounds
Taniguchi,Tsubaki,Take,Okumura,Terai,Shiokawa
, p. 896 - 902 (2007/10/02)
As part of our search for new agents for the treatment of overactive detrusor, 2,3- and 3,4-diphenylcyclopentylamines (3), 2,3-diphenyl-2-cyclopentenylamines (4), and related compounds (5 and 18) were synthesized and evaluated for inhibitory activity (i.v.) against urinary bladder rhythmic contraction in rats. Among them, some compounds involving N-tert-butyl-2,3-diphenyl-2-cyclopentenylamine (4b) exhibited inhibitory activity against bladder contraction superior to that of terodiline (2). Mydriatic activity (i.v.) of compound 4b in rats, an index of its side effects due to antimuscarinic activity, was found to be relatively weak in comparison with its inhibitory activity against bladder contraction. The pharmacological profile of 4b was examined in comparisen with that of terodiline. Most of the objective amines (3, 4, 5) were synthesized by preparation of Schiff bases from the corresponding cyclic ketones (6, 7, 8) and amines in the presence of TiCl4 in CH2Cl2 and subsequent reduction with NaBH4 in the presence of MeOH in one pot (method A).
