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CC BY 4.0 · Pharmaceutical Fronts 2023; 05(04): e227-e242
DOI: 10.1055/s-0043-1777345
Review Article

Pictet–Spengler-Based Multicomponent Domino Reactions to Construct Polyheterocycles

Jun-Duo Hu
1   Department of Pharmaceutical Engineering, College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People's Republic of China
,
Li-Liang Huang
1   Department of Pharmaceutical Engineering, College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People's Republic of China
,
Huang-Di Feng
1   Department of Pharmaceutical Engineering, College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People's Republic of China
2   Shanghai Frontiers Science Research Center for Druggability of Cardiovascular Noncoding RNA, Institute for Frontier Medical Technology, Shanghai University of Engineering Science, Shanghai, People's Republic of China
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Abstract

The Pictet–Spengler reaction is one of the important methodological arsenals in synthetic and medicinal chemistry, acting as an amenable tool for preparing tetrahydroisoquinoline, tetrahydro-β-carbolines, polycyclic skeletons, and value-added products. More than 100 years after its initial discovery, the Pictet–Spengler reaction's response has not withdrawn from the stage, but it has once again become the focus of attention with new features. The review summarizes recent advances in Pictet–Spengler-based multicomponent reactions from 2007 to 2022, including three-component and four-component Pictet–Spengler cyclization reactions in the presence of metal catalysts, organocatalysts, biological enzyme catalysts, and so on. These Pictet–Spengler-based multicomponent protocols provide an atom-/step economic approach for the synthesis of a library of new chemical entities.

Keywords

Pictet–Spengler reaction - multicomponent reactions - domino reactions - cyclization - heterocycles


Publication History

Received: 24 July 2023

Accepted: 04 November 2023

Article published online:
08 December 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)

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