Work

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

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide We report a metal-free method for the site-selective C6-β-aminoalkylation of tetrahydroquinolines using N -arylsulfonyl aziridines in HFIP at room temperature. HFIP activates aziridines through hydrogen bonding, promoting a regioselective S N 2-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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c02643

Authors: Yunus Taskesenligil, Murat Aslan, Nurullah Saracoglu

Institutions: Atatürk University, Ankara University

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Türkiye Bilimsel ve Teknolojik Araştırma Kurumu