Photoinduced Dearomative Multiple Functionalization of Quinolines to Construct Highly Substituted 3D Frameworks

Asuha Shimose; Yuki Nagashima

doi:10.1055/s-0043-1773519

Synlett, Table of Contents

Synlett 2025; 36(09): 1111-1122
DOI: 10.1055/s-0043-1773519

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Photoinduced Dearomative Multiple Functionalization of Quinolines to Construct Highly Substituted 3D Frameworks

Asuha Shimose

^aDepartment of Chemical Science and Engineering, Institute of Science Tokyo, O-okayama, Meguro-ku, Tokyo 152-8550, Japan

^bGraduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

,

Yuki Nagashima ∗

^bGraduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

^cFusion Oriented Research for disruptive Science and Technology (FOREST), Japan Science and Technology Agency (JST), Japan

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Abstract

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Abstract

Dearomative functionalization of quinolines expands the chemical diversity of highly functionalized 3D frameworks, such as 1,2,3,4- and 5,6,7,8-tetrahydroquinoline derivatives, which are important pharmacophores, with minimal synthetic costs. In this short review, we cover recent reports on the visible-light-induced dearomative functionalization of quinolines with an emphasis on reaction design/strategies and mechanistic studies and provide a theoretical basis for developing further dearomative syntheses in the future.

1 Introduction

2 Dearomative Functionalizations through the Formation of Photoexcited Quinolines

3 Dearomative Functionalizations through the Formation of Photoexcited Reagents/Intermediates

4 Conclusion

Key words

dearomative functionalization - photoinduced reactions - quinoline - tetrahydroquinoline - 3D frameworks - mechanistic studies - DFT calculations

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