Base-Promoted [4 + 3] Cycloadditions Enabling the Construction of Polycycle-Fused Uracils from N -Aminoisoquinolinium Derivatives

Organic Letters 2026

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Authors: Wen-Rong Wu, Yuan-Jie Meng, Juan Chen, Zifeng Yang, Xinxing Liu, Xinxing Liu, Xiang Liu, Xiang Liu, Pengju Feng, Shang‐Shi Zhang
DOI: 10.1021/acs.orglett.5c04929
Cited by: 3
References: 50

Abstract

As the sole nucleobase characteristic of RNA, uracil possesses a unique heterocyclic architecture that endows it with exceptional value as a privileged scaffold in medicinal chemistry. Herein, we report a versatile and efficient strategy for constructing polycyclic uracil derivatives through rare [4 + 3] cycloaddition reactions of N -aminoisoquinolinium, N -aminoquinolinium, or N -aminopyridinium salts with uracil-derived aldehydes. This protocol exhibits a broad substrate scope (36 examples), excellent functional-group tolerance, consistently high yields, and good scalability. The resulting products display diverse synthetic utility, as demonstrated by downstream derivatizations.

Fields of Study & Subjects

Click Chemistry and Applications Synthesis of heterocyclic compounds Catalytic C–H Functionalization Methods

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
3
Pages
960–965
Publication date
13 January 2026
Language
EN