1386
A. BAHY, Y. KACEM, AND B. BEN HASSINE
0.99 (d, 2CH3-iBu), 2.44 (m, CH-iBu), 2.60 (dd, H4, J ¼ 10.5 Hz, J ¼ 13.5 Hz), 2.85
(dd, H4’, J ¼ 6.9 Hz, J ¼ 13.5 Hz), 3.20 (dd, H, (CH2-iBu), J ¼ 14.1Hz, J ¼ 6.6 Hz),
3.52 (dd, H, (CH2-iBu), J ¼ 14.1Hz, J ¼ 9.3 Hz), 4.49 (dd, H3, J ¼ 6.9 Hz, J ¼ 10.5 Hz),
7.18–7.39 (m, 10Harom); 13C NMR (75.5 MHz, CDCl3): 20.5–20.9 (2CH3-iBu), 26.7
(3CH3-tBu), 28.2 (CH-iBu), 47.7 (C-tBu), 47.8 (C4), 60.0 (CH2-iBu), 65.2 (C3), 90.4
(C5), 126.1–140.9 (Carom), 154.9 (C7), 170.5 (C9). HRMS calcd. for C25H31N3O3
[M þ H]þ: 422.2444; found: 422.2438. Retention time (tR) ¼ 7.743.
2-Isopropyl-6-isobutyl-3-(2-methoxyphenyl)-8-phenyl-1-oxa-2,6,8-tria-
zaspiro[4.4]nonane-7,9-dione 13. White crystals (50%); mp ¼ 135–137 ꢀC (etha-
1
nol); Rf 0.34 (cyclohexane=ethyl acetate 90:10); H NMR (300 MHz, CDCl3): 0.90
(dd, 2CH3-iBu), 1.14 (dd, 2CH3-iPr), 2.23 (m, CH-iBu), 2.56 (dd, H4, J ¼ 8.1 Hz,
0
J ¼ 13.8 Hz), 3.06–3.36 (m, H4 , CH2-iBu, CH-iPr), 3.87 (OCH3), 4.91 (t, H3),
6.90–7.65 (m, 9Harom); 13C NMR (75.5 MHz, CDCl3): 17.9–21.8 (2CH3-iPr),
20.4–20.6 (2CH3-iBu), 28.2 (CH-iBu), 43.5 (C4), 47.7 (CH2-iBu), 55.6 (CH-iPr),
55.7 (OCH3), 61.1 (C3), 92.6 (C5), 110.8–132.0 (Carom), 155.0 (C7), 157.3
(C-OCH3), 170.8 (C9). HRMS calcd. for C25H31N3O4 [M þNa]þ: 460.2212; found:
460.2225. Retention time (tR) ¼ 6.107.
6-Isopropyl-2,3,8-triphenyl-1-oxa-2,6,8-triazaspiro[4.4]nonane-7,9-dione
14. White crystals (70%); mp ¼ 174–176 ꢀC (ethanol); Rf 0.34 (cyclohexane=ethyl
1
acetate 90:10); H NMR (300 MHz, CDCl3): 1.62 (dd, 2CH3-iPr), 2.86 (dd, H4,
0
J ¼ 10.5 Hz, J ¼ 13.5 Hz), 3.14 (dd, H4 , J ¼ 6.3 Hz, J ¼ 13.5 Hz), 4.25 (m, CH-iPr),
4.91 (dd, H3, J ¼ 6.3 Hz, J ¼ 10.5 Hz), 6.94–7.59 (m, 15Harom); 13C NMR
(75.5 MHz, CDCl3): 21.1 (2CH3-iPr), 45.8 (CH-iPr), 46.0 (C4), 71.3 (C3), 91.4 (C5),
120.1–137.4 (Carom), 148.6 (C7), 169.6 (C9). HRMS calcd. for C26H25N3O3 [M þ H]þ:
428.1974; found: 428.1979. Retention time (tR) ¼ 6.107.
2-Tert-butyl-6-isopropyl-3,8-diphenyl-1-oxa-2,6,8-triazaspiro[4.4]nonane-
7,9-dione 15. White crystals (60%); mp ¼ 147–149 ꢀC (ethanol); Rf 0.47
(cyclohexane=ethyl acetate 90:10); 1H NMR (300 MHz, CDCl3): 1.02 (s, 3CH3-
tBu), 1.61 (dd, 2CH3-iPr), 2.66 (dd, H4, J ¼ 10.8 Hz, J ¼ 13.2 Hz), 2.96 (dd, H4’,
J ¼ 6.6 Hz, J ¼ 13.2 Hz), 4.30 (m, CH-iPr), 4.55 (dd, H3, J ¼ 6.6 Hz, J ¼ 10.8 Hz),
7.29–7.49 (m, 10Harom); 13C NMR (75.5 MHz, CDCl3): 20.9–21.1 (2CH3-iPr), 26.4
(3CH3-tBu), 45.5 (CH-iPr), 48.6 (C4), 59.5 (C-tBu), 65.0 (C3), 90.1 (C5),
125.9–140.2 (Carom), 153.0 (C7), 170.1 (C9). HRMS calcd. for C24H29N3O3 [M þ H]þ:
408.2287; found: 408.2278. Retention time (tR) ¼ 7.283.
2,6-Diisopropyl-3-(2-methoxyphenyl)-8-phenyl-1-oxa-2,6,8-triazaspiro[4.4]-
nonane-7,9-dione 16. White crystals (60%); mp ¼ 129–131 ꢀC (ethanol); Rf 0.33
1
(cyclohexane=ethyl acetate 90:10); H NMR (300 MHz, CDCl3): 1.13 (dd, 2CH3-
iPr), 1.15 (dd, 2CH3-iPr), 2.50 (dd, H4, J ¼ 10.5 Hz, J ¼ 13.5 Hz), 3.11 (dd, H4’,
J ¼ 6.6 Hz, J ¼ 13.5 Hz), 3.15 (m, CH-iPr), 3.85 (OCH3), 3.98 (m, CH-iPr), 4.89 (t,
H3), 6.88–7.61 (m, 9Harom); 13C NMR (75.5 MHz, CDCl3): 16.9–21.5 (2CH3-iPr),
20.8–20.9 (2CH3-iPr), 44.1 (C4), 45.4 (CH-iPr), 54.9 (CH-iPr), 55.4 (OCH3), 60.5
(C3), 91.9 (C5), 110.5–131.4 (Carom), 153.0 (C7), 157.0 (C-OCH3), 170.3 (C9). HRMS
calcd. for C24H29N3O4 [M þ H]þ: 424.2237; found: 424.2244. Retention time
(tR ¼ 7.164).