, Volume 48, Issue 8, pp 1275-1277
Date: 08 Nov 2012

Unusual reaction of 1H-perimidines with sodium azide and benzoyl hydrazine in polyphosphoric acid

Rent the article at a discount

Rent now

* Final gross prices may vary according to local VAT.

Get Access
This is an excerpt from the content

Azapyrenes are used as organic luminophores and dyes, and they include compounds with high cytostatic and analgesic activity [13]. 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

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1366–1368, August, 2012.