42887-67-2Relevant articles and documents
Palladium-catalyzed chelation-assisted aromatic C-H nitration: Regiospecific synthesis of nitroarenes free from the effect of the orientation rules
Zhang, Wei,Lou, Shaojie,Liu, Yunkui,Xu, Zhenyuan
, p. 5932 - 5948 (2013/07/26)
A palladium-catalyzed chelation-assisted ortho-nitration of aryl C-H bond is described. A range of azaarenes such as 2-arylquinoxalines, pyridines, quinoline, and pyrazoles were nitrated with excellent chemo- and regioselectivity. Using the O-methyl oximyl group as a removable directing group, the regiospecific synthesis of a variety of o-nitro aryl ketones was achieved starting from aryl ketones via a three-step process involving the Pd-catalyzed ipso-nitration of C-H bond as a key step. Mechanistic investigations support a silver-mediated radical mechanism involving Pd((II/III) and/or Pd(II/IV) catalytic cycles under oxidizing conditions.
Ionic diamine rhodium complex catalyzed reductive N-heterocyclization of 2-nitrovinylarenes
Okuro, Kazumi,Gurnham, Joanna,Alper, Howard
experimental part, p. 4715 - 4720 (2011/07/08)
Ionic diamine rhodium complex (1) catalyzes the reductive N-cyclization of 2-vinylnitroarenes using carbon monoxide as a reducing agent to afford functionalized indoles. The catalytic system allows direct access to indoles with ester and ketone groups at the 2- or 3-position, in good yields.
Syntheses of Zindoxifene and Analogues by Titanium-Induced Oxo-Amide Coupling
Fuerstner, Alois,Jumbam, Denis N.,Seidel, Guenter
, p. 1125 - 1130 (2007/10/02)
Highly reactive titanium on graphite is used to reductively cyclize electron-rich acylamino carbonyl compounds 7, 8, 12, 14, and 16 to the corresponding indole derivatives 9, 10, 13, 15, and 17.Compound 9b is a known precursor of the mammary tumor-inhibiting compound zindoxifene (2).The other products are new analogues of this anticancer drug, exhibiting the substitution pattern previously recognized to be essential for high pharmacological activity. - Key Words: Indoles, 2-aryl- / Titanium graphite / Zindoxifene / Tumor-growth inhibitors / Alkylidenation, intramolecular