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Synlett 2024; 35(06): 603-615
DOI: 10.1055/a-2091-1071
DOI: 10.1055/a-2091-1071
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Special Issue to Celebrate the Centenary Year of Prof. Har Gobind Khorana
Recent Advances in the Synthesis of 5-(Hetero)aryl Uracil Derivatives
This work was supported by the National Key R&D Program of China (2020YFA0707901), National Natural Science Foundation of China (22022704, 2202270, and 22271291) and Chinese Academy of Sciences.
Dedicated to Professor Yong-Jun Chen on the occasion of his 60th birthday.
Abstract
C5-Aryl/heteroaryl uracil-based compounds have attracted continuous interest because of their wide biological potential. In this review, we outline the primary synthetic methods used to prepare designated uracils, various combinations of which have been used to synthesize target compounds with potential biological activities. The significance of each approach and its limitations are also summarized.
1 Introduction
2 Coupling of Prefunctionalized Uracils with (Hetero)aryl Reagents
2.1 Negishi Coupling
2.2 Suzuki–Miyaura Coupling
2.3 Stille Coupling
3 Coupling of Functionalized Uracils with Nonactivated Aromatic (Hetero)cycles
3.1 Photochemically Induced Coupling
3.2 Palladium-Catalyzed Coupling
4 Coupling of Nonactivated Uracil/Uridine with Functionalized Aromatic (Hetero)cycles
4.1 Electrochemical Reduction
4.2 Transition-Metal-Catalyzed Coupling
4.3 Light-Promoted Coupling of Uracils with Diazonium Salts
5 Direct Coupling of Nonactivated Uracils with Nonactivated Aromatic (Hetero)cycles
6 Summary and Prospects
Key words
uracils - cross-coupling reaction - prefunctionalization - direct coupling - nucleosides - medicinal chemistryPublication History
Received: 24 April 2023
Accepted after revision: 10 May 2023
Accepted Manuscript online:
10 May 2023
Article published online:
14 July 2023
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