An aza-Diels-Alder approach to chlorinated quinolines, benzoquinolines, and polybenzoquinolines

Juhwan Kim; Mehran J Umerani; Reina Kurakake; Huiting Qin; Joseph W Ziller; Alon A Gorodetsky; Young S Park

doi:10.1039/d0ra06744j

An aza-Diels-Alder approach to chlorinated quinolines, benzoquinolines, and polybenzoquinolines

RSC Adv. 2021 Apr 14;11(23):13722-13730. doi: 10.1039/d0ra06744j. eCollection 2021 Apr 13.

Authors

Juhwan Kim¹, Mehran J Umerani², Reina Kurakake², Huiting Qin¹, Joseph W Ziller³, Alon A Gorodetsky^{1

2

3}, Young S Park^{1

4}

Affiliations

¹ Department of Chemical and Biomolecular Engineering, University of California, Irvine Irvine CA 92697 USA alon.gorodetsky@uci.edu.
² Department of Materials Science and Engineering, University of California, Irvine Irvine CA 92697 USA.
³ Department of Chemistry, University of California, Irvine Irvine CA 92697 USA.
⁴ Department of Chemistry, Ulsan National Institute of Science and Technology (UNIST) 50 UNIST-gil Ulsan 44919 Republic of Korea youngspark@unist.ac.kr.

Abstract

Quinolines and quinoline-containing macromolecules are renowned for their valuable biological activities and excellent materials properties. Herein, we validate a general strategy for the synthesis of chloro-containing quinoline, benzoquinoline and polybenzoquinoline variants via the aza-Diels-Alder reaction. The described findings could be ultimately implemented in other synthetic pathways and may open new opportunities for analogous quinoline-derived materials.