The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline -oxides with -alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2'-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.
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http://dx.doi.org/10.1021/acs.orglett.4c04375 | DOI Listing |
Org Lett
December 2024
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline -oxides with -alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2'-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.
View Article and Find Full Text PDFOrg Biomol Chem
May 2024
School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), Beijing 102488, China.
A Lewis acid-promoted electrophilic thiocyanation/cyclization of -alkynylanilines for the synthesis of indole derivatives has been developed. The reaction utilizes MeSiBr as the Lewis acid and -thiocyanatosuccinimide as the thiocyanation reagent. A series of 2-aryl-3-thiocyanato indoles were prepared in moderate to high yields under mild conditions without metals and oxidants.
View Article and Find Full Text PDFChem Commun (Camb)
March 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China.
Herein, a palladium-catalyzed and ligand-controlled protocol for the divergent synthesis of pyrrole[2,3-]indole and urea derivatives has been described. Pyrrole[2,3-]indoles ("cyclization on" products) tandem cyclization of -alkynylanilines with isocyanides in the absence of a ligand and ureas ("cyclization off" products) oxidative amination of anilines with isocyanides in the presence of a ligand were obtained both in moderate to good yields with high selectivity. In this chemistry, cyclic and acyclic products were easily accessed with the same starting materials under the regulation of the ligand.
View Article and Find Full Text PDFChem Commun (Camb)
December 2023
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, China.
Cascade alkyl migration of 2-alkynylanilines an aromaticity destruction and reconstruction process is reported. The first alkyl migration is triggered by generation of a dearomatized arenium species oxidation and cyclization, and the second is driven by the force to restore the aromaticity of rearrangement products. The reaction gave rise to a range of multi-functionalized indoles.
View Article and Find Full Text PDFChem Commun (Camb)
July 2023
Department of Chemistry, Indian Institute of Technology Hyderabad (IITH) Kandi, 502284, Sangareddy, Telangana, India.
Substituted organoselenium compounds are crucial structural motifs in pharmaceutical molecules. Herein, we report a metal, oxidant, and base-free electrochemical approach to access 3-selenylindoles through an oxidative cyclization of 2-alkynylanilines with diselenides. This environmentally friendly approach demonstrates a wide range of substrate scope under mild reaction conditions in an electrochemical undivided cell setup.
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