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

Key words

enamines - cyclization - 1,3-dielectrophiles - heterocycles - purines - regioselectivity

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