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Synlett 2022; 33(05): 440-457
DOI: 10.1055/s-0040-1719845
DOI: 10.1055/s-0040-1719845
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Synthesis of Purines and Related Molecules by Cyclization Reactions of Heterocyclic Enamines
Abstract
A great variety of pharmacologically relevant fluorinated purine analogues are available by cyclization reactions of heterocyclic enamines with 1,3-dielectrophiles. The reactions usually proceed with excellent regioselectivities. As electrophiles, 1,3-diketones, enaminones or 3-chloro-2-en-1-ones were used. Other synthetic strategies are based on inverse-electron-demand Diels–Alder reactions of heterocyclic enamines with triazines. Purine analogues were further functionalized by transition-metal-catalyzed CH-coupling reactions or oxidative cyclizations, giving rise to more complex polycyclic products. Amidino-C-glycosides in their reactions with 1,3-dielectrophiles afforded pyrimidine-C-glycosides. Multicomponent reactions of heterocyclic enamines afforded complex products, including spirocyclic derivatives.
1 Introduction
2 1,3-Diketones
3 Enaminones
4 3-Chloro-2-en-1-ones
5 Triazines
6 Transition-Metal-Catalyzed Functionalizations
7 Pyrimidine-C-Nucleosides
8 Multicomponent Reactions
9 Conclusions
Publication History
Received: 06 September 2021
Accepted after revision: 15 September 2021
Article published online:
22 October 2021
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