Article 2026 · 0 citations

Site-Selective C6-β-Aminoalkylation of Tetrahydroquinolines with <i>N</i>-Arylsulfonyl Aryl Aziridines in Hexafluoroisopropanol: A Modular Approach to C6-Alkylated Quinolines

Taskesenligil, Yunus, Aslan, Murat, Saracoglu, Nurullah

Abstract

We report a metal-free method for the site-selective C6-beta-aminoalkylation of tetrahydroquinolines using N-arylsulfonyl aziridines in HFIP at room temperature. HFIP activates aziridines through hydrogen bonding, promoting a regioselective SN2-type ring opening. The method features broad functional group tolerance, high yields (up to 89%), and full stereochemical fidelity with chiral aziridines. Gram-scale synthesis with solvent recovery highlights its practicality, while postsynthetic oxidation provides direct access to C6-alkylated quinolines.

Keywords

C-H FUNCTIONALIZATION BOND ACTIVATION C-7 ACYLATION INDOLINES DYES VIRANTMYCIN ALKYLATION INHIBITORS LIGANDS DRUGS

WoS Categories

Chemistry, Organic

Citation

Journal: JOURNAL OF ORGANIC CHEMISTRY
Year: 2026
Volume: 91
Issue: 3
Pages: 1405-1411
ISSN: 0022-3263
eISSN: 1520-6904
DOI: 10.1021/acs.joc.5c02643
WoS UID: WOS:001659279400001

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