A novel method for the synthesis of 1,8-dihydropyrido[2,3,4-gh]perimidin-7(6H)-ones
Rent the article at a discountRent now
* Final gross prices may vary according to local VAT.Get Access
Many organic luminphores and dyes are polynuclear aromatic and heteroaromatic compounds, including pyrene and its heterocyclic analogs. Effective medicines, (e.g., the antitumor compound AG 311) and luminescent intercalators have been discovered on the basis of 4,9-diazapyrenes [1–3].
At this time the majority of azapyrenes are unavailable. Primarily this is due to the absence of efficient methods for the peri-annelation of heterocyclic rings. In this study, we propose a method for the peri-annelation of an [ab]pyridine ring to perimidines, which is based on a previously unknown intramolecular variant of our recently discovered acetamidation of aromatic compounds using nitroalkanes in polyphosphoric acid (PPA) [4,5].
We have shown that the reaction of the perimidines 1a-c with 1.05-fold molar excess of β-nitrostyrene (2) in PPA for 5 h at 65-70°C led to previously unknown 8-phenyl-1,8-dihydropyrido[2,3,4-gh]perimidin7(6H)-ones 6a-c in 76-84% yields.
The reaction mechanism probably include
- 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
- A. 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)].
- A novel method for the synthesis of 1,8-dihydropyrido[2,3,4-gh]perimidin-7(6H)-ones
Chemistry of Heterocyclic Compounds
Volume 48, Issue 8 , pp 1269-1271
- Cover Date
- Print ISSN
- Online ISSN
- Springer US
- Additional Links
- polyphosphoric acid
- Industry Sectors