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
Rent the article at a discountRent now
* Final gross prices may vary according to local VAT.Get Access
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 ...
- M. D. Varney, C. L. Palmer, J. G. Deal, S. Webber, K. M. Welsh, C. A. Bartlett, C. A. Morse, W. W. Smith, and C. A. Janson, J . Med. Chem., 38, 1892 (1995). CrossRef
- S. Roknic, L. Glavas-Obrovac, I. Karner, I. Piantanida, M. Zinic, and K. Pavelic, Chemotherapy, 46, 143 (2000). CrossRef
- H.-C. Becker and B. Norden, J . Am. Chem. Soc., 119, 5798 (1997). CrossRef
- А. V. Aksenov, N. A. Aksenov, O. N. Nadein, and I. V. Aksenova, Synlett, 2628 (2010).
- A. V. Aksenov, N. A. Aksenov, O. N. Nadein, and A. E. Tsys, Khim. Geterotsikl. Soedin., 1265 (2010). [Chem. Heterocycl. Compd., 46, 1025 (2010)].
- 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
- Cover Date
- Print ISSN
- Online ISSN
- Springer US
- Additional Links
- polyphosphoric acid
- Industry Sectors