23210-25-5Relevant articles and documents
Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives
Ece, Hamdiye,Tange, Yuji,Yurino, Taiga,Ohkuma, Takeshi
, p. 935 - 939 (2021/02/22)
3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc) 2. Wide varieties of diethyl phosphates derived from N -arylmandelamides were converted almost quantitatively into oxindoles. When N, N -dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.
Enantioselective Arylation of Oxindoles Using Modified BI-DIME Ligands
Mangunuru, Hari P. R.,Malapit, Christian A.,Haddad, Nizar,Reeves, Jonathan T.,Qu, Bo,Rodriguez, Sonia,Lee, Heewon,Yee, Nathan K.,Song, Jinhua J.,Busacca, Carl A.,Senanayake, Chris H.
, p. 4435 - 4443 (2018/11/21)
The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i -Pr-BI-DIME and Me 2 -BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd 2 (dba) 3 / i -Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me 2 -BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.
Reduction of 3-aminoquinoline-2,4(1H,3H)-diones and deamination of the reaction products
Klásek, Antonín,Ly?ka, Antonín,Rouchal, Michal,Rudolf, Ond?ej,R??i?ka, Ale?
, p. 595 - 612 (2014/06/09)
3-Aminoquinoline-2,4-diones were stereoselectively reduced with NaBH 4 to give cis-3-amino-3,4-dihydro-4-hydroxyquinolin-2(1H)-ones. Using triphosgene (=bis(trichloromethyl) carbonate), these compounds were converted to 3,3a-dihydrooxazolo[4,5-