Synthesis of novel 1,2,3,6-tetraazapyrene heterocyclic system representatives – 3,8-dihydropyrido[2',3',4':4,5]naphtho-[1,8-de][1,2,3]triazin-7(6H)-ones
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Amongst the few azapyrenes synthesized to this time, a series of compounds have been found having useful properties as organic luminophores, dyes, and effective medicines [1–3].
The poor availability of azapyrenes probably is mostly due to the absence of efficient methods for the peri-annelation of heterocyclic rings. In this work, we propose a method for the peri-annelation of an [ab]pyridine ring to the 1H-naphtho[1,8-de][1,2,3]triazine (1) through its reaction with β-nitrostyrenes.
We have shown that reaction of naphthotriazine 1 with a 1.05-fold molar excess of β-nitrostyrenes 2a-c for 3 h in PPA at 65-70°C gives the previously unknown 8-aryl-3,8-dihydropyrido[2',3',4':4,5']naphtho[1,8-de][1,2,3]triazin-7(6H)-ones 6a-c in 23-37% yields.
The reaction mechanism probably includes successive alkylation of the naphthotriazine 1 by the β-nitrostyrenes 2a-c to form the nitro compounds 3a-c and an intramolecular variant of our recently discovered acetamidation reaction of aromatic compounds b
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- Synthesis of novel 1,2,3,6-tetraazapyrene heterocyclic system representatives – 3,8-dihydropyrido[2',3',4':4,5]naphtho-[1,8-de][1,2,3]triazin-7(6H)-ones
Chemistry of Heterocyclic Compounds
Volume 48, Issue 8 , pp 1272-1274
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