To a solution of dienone 2 [1] (1 g, 3.4 mmol) in absolute ethanol (20 mL) was added 4-methyl o-phenylenediamine 1 (0.41 g, 3.4 mmol) and the mixture was refluxed for 1 hour [2,3]. The solid was then filtered and washed twice with 10 mL of ethanol to afford product 3 as an orange solid (1.14 g, 88%).
Melting point: 180-181°C.
IR (KBr, cm-1): 1560 (C=O); 1240 (C=C).
1H-NMR (200 MHz, CDCl3, δ, ppm): 8.05 (m, 4H, -CH Benz); 7.56 (m, 6H, -CH Benz.bis: p-H, m-H); 7.12 (m, 3H, -CH Benz); 6.57 (s, 2H, -CHCO); 2.48 (s, 3H, CH3).
E. A: Anal. Calc. for C25H20N2O2: C 78.93, H 5.30, N 7.36, Found: C 79.04, H 5.30, N 7.07.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3References and Notes
- Saalfrank, R. W.; Lôw, N.; Demleitner, B.; Stalk, D.; Teichert, M. Chem. Eur. J. 1998, 4, 1305.
- Touzani, R.; Benhadda, T.; Elkadiri, S.; Ramdani, A.; Maury, O.; Lebozec, H.; Toupet, L.; Dixneuf., P. H. New. J. Chem. 2001, 25, 391–394.
- Waring, M. J.; Ben-hadda, T.; Kotchevar, A. T.; Ramdani, A.; Touzani, R.; El Kadiri, S.; Hakkou, A.; Bouakka, M.; Ellis, T. Molecules 2002, 7, 641–656.
- Sample availability: available from the authors.
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