Unusual reaction of 1H-perimidines with sodium azide and benzoyl hydrazine in polyphosphoric acid
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Azapyrenes are used as organic luminophores and dyes, and they include compounds with high cytostatic and analgesic activity [1–3]. None the less there are a limited number of methods for the synthesis of such compounds, particularly those with functional groups. In this work, we propose a one-pot method for preparing the 10-amino-1,2,6,8-tetraazapyrenes 8a-c, based on our recently discovered method for the amination of perimidines with sodium azide in polyphosphoric acid (PPA) [4,5].
It was found that a reaction of perimidines 1a-c with NaN3 in PPA at 70-80°C, and further with benzoyl hydrazine in the ratio 1:3:1 at 125-135°C gave the previously unknown 10-amino-1,2,6,8-tetraazapyrenes 8a-c in 34-41% yields.
The reaction scheme, as reported in the studies [4,5], includes the formation of the intermediates 2a-c which are acylated by benzoyl hydrazine to give compounds 3a-c (found in equilibrium with 4a-c). Through an intramolecular nucleophilic substitution the latter are converted to th ...
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- Unusual reaction of 1H-perimidines with sodium azide and benzoyl hydrazine in polyphosphoric acid
Chemistry of Heterocyclic Compounds
Volume 48, Issue 8 , pp 1275-1277
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- benzoyl hydrazine
- polyphosphoric acid
- sodium azide
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