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Freshly distilled cyclopentadiene 17 (1.05 g, 15.9 mmol) was added dropwise to a solution of the carbazoledione 3 (1 g, 5.3 mmol) in CH 2 Cl 2 (40 ml) stirred and cooled at 10 °C. The stirring was continued for 5 h at 10 °C then for 12 h at room temperature. The solution was concentrated under vacuum and the resulting residue was chromatographed on silica gel using CH 2 Cl 2 /MeOH (97 : 3) as the eluent Compound 18 was obtained as a yellow solid in 49% yield, mp 182 °C. IR (KBr) cm 1 : 3260 1700, 1640. 1 H- NMR (CDCl 3 ) d: 8.9 (1H, s, NH), s, H-12). 13 C-NMR (DMSO-d 6 ) d: 199, 1H, t, J5.3, 3.0 Hz, H-2 or H-3), 4.1 (1H, dd, J7.2, 3.8 Hz, H-11c), 3.59 (2H, s, p.5811 ,
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71 (s, 3H, 6'-CH 3, pp.7-4881 ,
36 (d, J = 8.2 Hz, 1H, 5-H) 13 C NMR (75 MHz, CDCl 3 ): ? ppm 15 ,
CDCl 3 ): ? ppm 15, 13 C NMR (75 MHz ,
38 mmol) in EtOH (50 mL) was added benzyl bromide (1130 mg, 6.61 mmol) or 4-methoxybenzyl bromide (1330 mg, 6.61 mmol). The solution was heated at reflux for 24 h, cooled ,
The orange reaction suspension was concentrated in vacuum then filtered to yield compound (6a) as an orange solid which was purified by recristallization from EtOH. It was obtained in 50% yield (90 mg). mp 279 °C IR (KBr): 1678, 1667, 1652 cm -1 . 1 H NMR (300 MHz98 (s, 2H, CDCl 3 ): ? ppm 1.48 (t, J = 7.0 Hz, 3H, CH 2 CH 3 ), 4.76), 8.33 (d, J = 7.2 Hz, 1H, 9-H). 13 C NMR (75 MHz, p.865 ,
94 (s, 2H, pp.48-52 ,