(2H, m, H-4 and H-6 of the aromatic ring), 7.92 (1H, dd, J = 4.5, 7.8 Hz, H-5 of the aromatic ring), 8.09 (1H, s, H-2 of adenine), 8.23 (1H, d, J = 8.3 Hz, H-3 of the aromatic ring), 8.48 (1H, s, H-8 of adenine); 13C NMR (DMSO-d6): d 118.4, 125.7, 127.4, 129.6, 130.2, 134.8, 139.7, 144.4, 149.8, 153.2, 156.2; MS (m/z): 256 (M+); Anal. calcd. for C11H8N6O2: C, 51.56; H, 3.15; N, 32.80. Found: C, 51.74; H, 2.92; N. 32.96.
9-(2,4-Dinitro-phenyl)-9H-purin-6-ylamine (2b). Column chromatography on silica gel eluting with EtOAc-n-hexane (3:1) gave yellowish brown solid; mp 285-287 °C (Lit.8a mp 286-288 °C); 1H NMR (DMSO-d6): d 7.55 (2H, s, NH2), 8.08 (1H, s, H-2 of adenine), 8.19 (1H, d, J = 8.7 Hz, H-6 of the aromatic ring), 8.57 (1H, s, H-8 of adenine), 8.74 (1H, d, J = 8.7 Hz, H-5 of the aromatic ring), 8.93 (1H, s, H-3 of the aromatic ring).
6-Chloro-9-(2,4-dinitro-phenyl)-9H-purine (2c). Column chromatography on silica gel eluting with EtOAc-n-hexane (1:3) gave pale red solid; mp 169-171 °C (Lit.8a mp 167-169 °C); 1H NMR (DMSO-d6): d 8.21 (1H, d, J = 8.7 Hz, H-6 of the aromatic ring), 8.62 (1H, s, H-8 of 6- chloropurine), 8.73 (1H, d, J = 8.7 Hz, H-5 of the aromatic ring), 8.92 (1H, s, H-3 of aromatic ring), 9.01 (1H, s, H-2 of 6-chloropurine).
9-(3-Nitropyridin-2-yl)-9H-purin-6-one (2d). Column chromatography on silica gel eluting with EtOAc gave yellow solid; mp 252-254 °C (Lit.8a mp 253-255 °C); 1H NMR (DMSO-d6): d 7.88 (1H, dd, J = 4.8, 8.1 Hz, H-5 of pyridine), 8.06 (1H, s, H-2 of hypoxanthin), 8.59 (1H, s, H- 8 of hypoxanthin), 8.71 (1H, d, J = 8.2 Hz, H-4 of pyridine), 8.95 (1H, d, J = 4.8 Hz, H-6 of pyridine), 12.76 (1H, br, NH).
Acknowledgements
The authors thank Payame Noor University for the financial support of this work.
References and Notes
1. (a) Clark, J. H.; Rhodes, C. N. Clean Synthesis Using Porous Inorganic Solid Catalysts and Supported Reagents; 1st Edn., Royal Society of Chemistry: London, 2000. (b) Sheldon, R. A.; van Bekkum, H. Fine Chemicals Through Heterogeneous Catalysis; 1st Edn., Wiley-VCH: Weinheim, 2001. (c) Kybett, A. P.; Sherrington, D. C. Supported Catalysts and their Applications; 1st Edn., Royal Society of Chemistry: London, 2001. (d) Salehi, P.; Zolfigol, M. A.; Shirini, F.; Baghbanzadeh, M. Curr. Org. Chem. 2006, 10, 2171 (Review). (e) Hasaninejad, A.; Zare, A.; Sharghi, H.; Shekouhy, M. ARKIVOC 2008, (xi), 64. (f) Khalafi- Nezhad, A.; Zare, A.; Parhami, A.; Soltani Rad, M. N.; Nejabat, G. R. J. Iran. Chem. Soc. 2007, 4, 271. (g) Hasaninejad, A.; Zare, A.; Sharghi, H.; Shekouhy, M.; Khalifeh, R.; Salimi Beni, A.; Moosavi Zare, A. R. Can. J. Chem. 2007, 85, 416. (h) Khalafi-Nezhad, A.; Zare,
