Ru(II)-Catalyzed Regioselective Hydroxymethylation of β-Carbolines and Isoquinolines via C-H Functionalization: Probing the Mechanism by Online ESI-MS/MS Screening
Autor
Tokala R.
Bora D.
Sana S.
Nachtigall F.M.
Santos L.S.
Shankaraiah N.
Resumen
A Ru(II)-catalyzed regioselective C-H activation toward hydroxymethylation of β-carbolines and isoquinolines as effective directing groups has been developed, and the mechanism was probed by using online electrospray ionization-tandem mass spectrometry. The introduction of the hydroxymethyl group in the biologically relevant molecules routed via C-H functionalization remains an important task. Gratifyingly, this protocol draws attention to the regioselective formation of monohydroxymethylated β-carboline/isoquinoline products exclusively. © 2019 American Chemical Society.
Colecciones
Ítems relacionados
Mostrando ítems relacionados por Título, autor o materia.
-
Article
Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement (2020)
Sathish, Manda; Nachtigall, Fabiane Manke; Santos, Leonardo S. (Royal Society of Chemistry, 2020-10-21)Tetrahydro-β-carboline (THBC) is a tricyclic ring system that can be found in a large number of bioactive alkaloids. Herein, we report a simple and efficient method for the synthesis of enantiopure THBCs through a chiral ... -
Article
Nickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor–Acceptor Cyclopropanes (2024)
Quezada, Víctor; Castroagudín, Mariña; Verdugo, Felipe; Ortiz, Sergio; Zaragoza, Guillermo; Nachtigall, Fabiane M.; Reis, Francisco A. A.; Castro-Alvarez, Alejandro; Santos, Leonardo S.; Nelson, Ronald (Multidisciplinary Digital Publishing Institute (MDPI), 2024)This article describes the development of a nickel-catalyzed regio- and diastereoselective formal [3+2] cycloaddition between N-substituted indoles and donor–acceptor cyclopropanes to synthesize cyclopenta[b]indoles. ... -
Article
Copper (II) as catalyst for intramolecular cyclization and oxidation of (1,4-phenylene)bisguanidines to benzodiimidazole-diylidenes (2020)
Mesias-Salazar A.; Trofymchuk O.S.; Daniliuc C.G.; Antiñolo A.; Carrillo-Hermosilla F.; Nachtigall F.M.; Santos L.S.; Rojas R.S. (Academic Press Inc., 2020)