The site-selective C8-alkylation of quinolines has been accomplished using cyclopropyl alcohols as the alkylating agents and -oxide as a weak chelating group in the presence of Co(III) catalysis via merging C-H/C-C bond activation. The use of cyclopropanol as the alkyl source, Co catalysis, substrate scope, HRMS analysis of the reaction intermediate, and late-stage mutation of drug molecules/natural products are the important practical features.
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Site-Selective C8-Alkylation of Quinolines with Cyclopropanols: Merging C-H/C-C Bond Activation.
Org Lett
November 2023
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, Assam 781039, India.
The site-selective C8-alkylation of quinolines has been accomplished using cyclopropyl alcohols as the alkylating agents and -oxide as a weak chelating group in the presence of Co(III) catalysis via merging C-H/C-C bond activation. The use of cyclopropanol as the alkyl source, Co catalysis, substrate scope, HRMS analysis of the reaction intermediate, and late-stage mutation of drug molecules/natural products are the important practical features.
View Article and Find Full Text PDFSite-Selective C8-Alkylation of Quinoline -Oxides with Maleimides under Rh(III) Catalysis.
J Org Chem
June 2021
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
The site-selective modification of quinolines and their analogs has emerged as a pivotal topic in medicinal chemistry and drug discovery. Herein, we describe the rhodium(III)-catalyzed C8-alkylation of quinoline -oxides with maleimides as alkylating agents, resulting in the formation of bioactive succinimide-containing quinoline derivatives. The reaction proceeds under mild conditions with complete functional group tolerance.
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