1403336-41-3Relevant articles and documents
Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles
Mintz, Tomer,More, Nagnath Yadav,Gaster, Eden,Pappo, Doron
, p. 18164 - 18178 (2021/12/17)
In this study, a novel iron-catalyzed oxidative cross-coupling reaction between phenols and 3-alkyloxindole derivatives is reported. The efficient method, which is based on the FeCl3 catalyst and the t-BuOOt-Bu oxidant in 1,2-dichloroethane at 70 °C, affords 3-alkyl-3-(hydroxyaryl)oxindole compounds with a high degree of selectivity. The generality of the conditions was proven by reacting various substituted phenols, naphthols, and tyrosine derivatives with 3-alkyloxindoles. To apply the chemistry for the conjugation of tyrosine-containing short peptides with oxindolylalanine (Oia) derivatives, the reaction conditions were modified [Fe(O2CCF3)3 catalyst, t-BuOOt-Bu, HFIP, 70 °C], and amino acids with acid-stable N-protecting groups were used.
Lewis acid-catalyzed Friedel-Crafts alkylations of 3-hydroxy-2-oxindole: An efficient approach to the core structure of azonazine
Ghosh, Santanu,Kinthada, Lakshmana K.,Bhunia, Subhajit,Bisai, Alakesh
, p. 10132 - 10134 (2012/11/13)
A Lewis acid catalyzed Friedel-Crafts reaction of electron rich aromatics with 3-alkyl-3-hydroxy-2-oxindole (5) has been developed. The methodology provides a straightforward access to the core of azonazine (2) sharing an all-carbon quaternary stereocenter at the tetracyclic ring junction. The Royal Society of Chemistry 2012.
