83463-80-3Relevant academic research and scientific papers
NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines
Chen, Qian,Gao, Yang,Hu, Xiao-Qiang,Huo, Yanping,Li, Xianwei,Yang, Simin
, p. 7772 - 7779 (2021/06/30)
Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.
Photochemistry of 2-Phenylbenzothiazole with Ethoxyacetylene and Ethoxypropyne. Synthesis of 1,5-Benzothiazepines
Sindler-Kulyk, M.,Neckers, D. C.
, p. 4914 - 4919 (2007/10/02)
Photocycloaddition reactions of 2-phenylbenzothiazole with electron-rich alkynes, ethoxyacetylene, and ethoxypropyne gave substituted 1,5-benzothiazepines in a one-step processes.
