1359715-97-1Relevant articles and documents
Synthesis of α-Ketone-isoquinoline Derivatives via Tandem Ruthenium(II)-Catalyzed C-H Activation and Annulation
Wu, Xiao-Lin,Dong, Lin
, p. 6990 - 6993 (2018)
A new ruthenium(II)-catalyzed tandem C-H activation/cyclization/hydrolysis cascade process of 2H-imidazoles and alkynes for facile and regioselective access to α-ketone-isoquinolines has been successfully developed. 2H-Imidazole as the novel traceless directing group has been well applied in this paper. The protocol features mild reaction conditions and easily accessible starting materials, and α-ketone-isoquinolines could be applied to further construct more complex heterocyclic compounds.
Synthesis of 1-Benzyl-, 1-Alkoxyl-, and 1-Aminoisoquinolines via Rhodium(III)-Catalyzed Aryl C-H Activation and Alkyne Annulation
Zhou, Yiming,Hua, Ruimao
, p. 8862 - 8872 (2021/07/20)
One-pot syntheses of 1-benzyl-, 1-Alkoxyl-, and 1-Alkylamino-isoquinolines through automatic directing group (DGauto)-Assisted, rhodium(III)-catalyzed aryl C-H activation and annulation with internal alkynes were developed. The reactions affording 1-benzylisoquinolines involve a cascade oximation of diarylacetylenes with hydroxylamine, forming aryl benzyl ketone oxime, and oxime-Assisted rhodium(III)-catalyzed aryl C-H activation and followed annulation with another molecule of diarylacetylene in a one-pot manner. The formation of 1-Alkoxyl/amino isoquinolines includes the addition of nucleophilic alcohols or amines to aryl nitriles, imine-Assisted rhodium-catalyzed aryl C-H activation, and subsequent alkyne annulation.
Easy Access to 1-Amino and 1-Carbon Substituted Isoquinolines via Cobalt-Catalyzed C - H/N - O Bond Activation
Muralirajan, Krishnamoorthy,Kuppusamy, Ramajayam,Prakash, Sekar,Cheng, Chien-Hong
, p. 774 - 783 (2016/03/09)
A green atom-economical method for the synthesis of highly functionalized 1-amino and 1-carbon substituted isoquinolines from the reaction of N′-hydroxybenzimidamides and aryl ketoximes, respectively, with alkynes via pentamethylcyclopentadienylcobalt(III)-catalyzed C - H/N - O bond activation is described. The external oxidant-free annulation reaction uses the =NOH moiety in N′-hydroxybenzimidamides or N-aromatic ketone oximes as the directing group and internal oxidant. This first row transition metal-catalyzed annulation serves as an efficient alternative for the synthesis of isoquinolines, as water is the only by-product and expensive noble metals such as rhodium(III), iridium(III), palladium(II), and ruthenium(II) are not required. The reaction proceeds via C - H activation, alkyne insertion, reductive elimination, and N - O activation.