Synthesis and transformations of pyrrolo[1,2-a][1,3,5]-triazines |
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Authors: | Jonas Verhoeven B Narendraprasad Reddy Lieven Meerpoel Jan Willem Thuring Guido Verniest |
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Institution: | 1. Research Group of Organic Chemistry, Department of Chemistry and Department of Bioengineering Sciences, Faculty of Sciences and Bioengineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium;2. Janssen Research & Development, Turnhoutseweg 30, B-2340 Beerse, Belgium |
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Abstract: | Pyrrolotriazines and related fused azaheterocycles have high potential for the synthesis of bioactive compounds, especially as a purine base isoster in carbon linked nucleosides. Although many structurally related compounds have already been synthesized and used in medicinal chemistry, pyrrolo1,3,5]triazines have barely been described. The present work describes the synthesis of such heterocycles via condensation of 2-amino-3-ethoxycarbonylpyrrole with ethoxycarbonyliso(thio)cyanate. In a brief reactivity study of the obtained fused pyrroles, O- and S-alkylation, ester hydrolysis as well as regioselective bromination at the 6-position was demonstrated. |
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Keywords: | Pyrrolotriazines Bromination Cyclocondensation Aminopyrrole Nucleoside analogues |
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