8115
3. (a) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Heathcock, C. H.; Vol. 2. Ed. Pergamon
Press: New York, 1991; Vol. 2. (b) Reser, A.; Leyshon, L. J.; Saunders, D.; Mijovic, M. V.; Bright, A.; Bogie,
J. J. Am. Chem. Soc. 1972, 94, 2414.
4. (a) Roussilhe, J.; Despax, B.; Lopez, A.; Pailous, N. J. Chem. Soc., Chem. Commun. 1982, 380. (b) Roussilhe, J.;
Fargin, E.; Lopez, A.; Despax, B.; Pailous, N. J. Org. Chem. 1983, 48, 3736. (c) Fery-Forgues, S.; Paillous, N.
J. Org. Chem. 1986, 51, 672. (d) Houpis, I. N.; Molina, A.; Lynch, J.; Reamer, R. A.; Volante, R. P.; Reider, P.
J. J. Org. Chem. 1993, 58, 3176. (e) Dryanska, V.; Ivanov, Chr. Synthesis 1976, 37.
5. (a) Evans, D. A.; Sacks, C. E.; Kleschick, W. A.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789. (b) Houpis,
I. N.; Molina, A.; Lynch, J.; Reamer, R. A.; Volante, R. P.; Reider, P. J. J. Org. Chem. 1993, 58, 3176. (c)
Advani, S. B.; Sam, J. J. Pharm. Sci. 1968, 57, 1693. (d) Kay, J. M.; Smith, P.; Heath, D.; Will, J. A. Cardiovasc.
Res. 1976, 10, 200. (e) Badin, J.; Tinland, B. Res. Commun. Chem. Pathol. Pharmacol. 1973, 6, 1099. (f) Dunwell,
D. W.; Evans, D. J. Med. Chem. 1977, 20, 797. (g) Sato, Y.; Imai, M.; Amano, K.; Iwamatsu, K.; Konnno, F.;
Kurata, Y.; Sakakibara, S.; Hachisu, M.; Izumi, M.; Matsuki, N.; Saito, H. J. Med. Chem. 1998, 41, 3015.
6. Desali, R. D.; Hunter, R. F.; Rahman Khan Khakidi, A. J. Chem. Soc. 1934, 1186.
7. (a) Hein, D. W.; Alheim, R. J.; Leavitt, J. J. J. Am. Chem. Soc. 1957, 79, 427. (b) Galatis, L. C. J. Am. Chem.
Soc. 1948, 70, 1967. (c) Oliveros, L. Bull. Soc. Chim. Fr. 1974, 2628. (d) Tseitlin, G. M.; Takarev, B. V.; Kulagin,
V. N. J. Org. Chem. 1982, 18, 931. (e) Nelson, R. E.; Matchett, J. R.; Tindall, J. B. J. Am. Chem. Soc. 1928, 50,
922. (f) Perry, R. J. J. Org. Chem. 1992, 57, 2883. (g) Tseitlin, G. M.; Tokarev, B. V.; Kulagin, V. N. J. Org.
Chem. 1982, 18, 931. (h) Ramana, D. V.; Kantharaj, E. J. Chem. Soc. Perkin Trans. 2, 1995, 1497.
8. (a) Hiratani, K.; Kasuga, K.; Goto, M.; Uzawa, H. J. Am. Chem. Soc. 1997, 119, 12677. (b) Hiratani, K.;
Takahashi, T.; Kasuga, K.; Sugihara, H.; Fujiwara, K.; Ohashi, K. Tetrahedron Lett. 1995, 36, 5567. (c) Hiratani,
K.; Uzawa, H.; Kasuga, K.; Kambayashi, H. Tetrahedron Lett. 1997, 38, 8993.
1
9. 1a: Colorless solid; mp 131.1–133.5°C; H NMR (CDCl3): l 2.08 (s, 3H, ꢀCH3), 4.72 (s, 4H, ꢀCH2ꢀOꢀ), 5.44 (s,
2H, CH2ꢁC), 6.91 (d, J=7.8 Hz, 2H, Ar), 6.98–7.02 (m, 4H, Ar), 7.75 (bs, 1H, NH), 8.32 (d, J=7.3, 2H, Ar).
IR (KBr): 3296, 1660, 1600, 1260 cm−1. HRMS calcd for C20H22N2O4 354.1578, found 354.1574. 1b: Colorless
1
solid; mp 119.2–123.0°C; H NMR (CDCl3): l 4.78 (s, 4H, ArꢀCH2ꢀ), 5.48 (s, 2H, CH2ꢁC), 7.18 (d, J=7.0, 2H,
Ar), 7.27 (t, J=7.8, 2H, Ar), 7.42–7.48 (m, 6H, Ar), 7.62 (dd, J=0.9, 7.9, 2H, Ar), 8.06 (dd, J=1.4, 8.2, 4H, Ar).
IR (KBr): 3431, 3338, 1656, 1602, 1258, cm−1. HRMS calcd for C30H26N2O4 478.1891, found 478.1803. 1c:
1
Colorless solid; mp 149.3–151.0°C; H NMR (CDCl3): l 2.06 (s, 3H, CH3ꢀC(ꢁO)ꢀ), 2.30 (s, 3H, CH3ꢀAr), 4.68
(s, 4H, ꢀCH2ꢀOꢀ), 5.40 (s, 2H, CH2ꢁC), 6.80 (s, 2H, Ar), 7.73 (bs, 1H, NH), 8.17 (s, 2H, Ar). IR (KBr): 3288,
1660, 1262 cm−1. HRMS calcd for C22H26N2O4 382.1891, found 382.1929. 1d: Colorless solid; mp 131.8–133.7°C;
1H NMR (CDCl3): l 2.33 (s, 3H, CH3ꢀAr), 4.73 (s, 4H, ꢀCH2ꢀOꢀ), 5.45 (s, 2H, CH2ꢁC), 6.79–6.80 (m, 4H, Ar),
7.40 (t, J=7.7, 4H, Ar), 7.49 (t, J=7.5, 2H, Ar), 7.78–7.80 (m, 4H, Ar), 8.36 (s, 2H, Ar), 8.49 (bs, 1H, NH). IR
(KBr): 3444, 3425, 1669, 1595, 1253 cm−1. HRMS calcd for C32H30N2O4 506.2204, found 506.2249.
10. The reaction of 2-N-benzoyl aminophenol with 3-chloro-2-chlorometyl-1-propene in the presence of NaH did not
give 1b, but the [1+1] cyclic compound obtained in 70% yield by O- and N-alkylation of the isobutenyl dichloride
with hydroxyl and amide groups, respectively. KOH could be also used as a base for the etherification in ethanol.
1
11. 2a: Colorless solid; mp 94.7–96.7°C; H NMR (CDCl3): l 2.58 (s, 6H, CꢀCH3), 3.59 (s, 4H, ArꢀCH2ꢀ), 4.93 (s,
2H, CH2ꢁC), 7.09 (d, J=7.4, 2H, Ar), 7.21 (t, J=7.7, 2H, Ar), 7.50 (d, J=7.9, 2H, Ar). IR (KBr): 1614, 1268
cm−1. HRMS calcd for C20H18N2O2 318.1367, found 318.1362. 3a: Colorless oil; 1H NMR (CDCl3): l 1.44 (s, 3H,
CH3ꢀC(ꢀOꢀ)), 2.09 (s, 3H, ꢀC(ꢁO)CH3), 2.54 (s, 3H, CH3), 2.96 (d, J=15.4, 1H, ArꢀCHꢀ), 3.11 (d, J=13.8, 1H,
ArꢀCHꢀ), 3.19 (d, J=15.4, 1H, ArꢀCHꢀ), 3.28 (d, J=13.8, 1H, ArꢀCHꢀ), 6.75 (t, J=7.7, 1H, Ar), 6.79 (d,
J=6.8, 1H, Ar), 7.07 (d, J=7.6, 1H, Ar), 7.17 (t, J=7.7, 1H, Ar), 7.47 (d, J=7.9, 1H, Ar), 8.00 (d, J=7.9, 1H,
Ar). IR (KBr): 3277, 1671, 1624 cm−1. HRMS calcd for C20H20N2O3 336.1473, found 336.1478. 4a: Colorless
1
solid; mp 77.4–78.8°C; H NMR (CDCl3): l 2.54 (s, 3H, CꢀCH3), 2.56 (s, 3H, CꢀCH3), 3.37 (s, 2H, ArꢀCH2ꢀ),
3.45 (s, 2H, ArꢀCH2ꢀ), 4.81 (s, 1H, CH2ꢁC), 4.82 (s, 1H, CH2ꢁC), 7.00–7.02 (m, 4H, Ar), 7.15 (t, J=7.7, 1H, Ar),
7.38 (s, 1H, Ar), 7.43 (d, J=8.0, H, Ar). IR (KBr): 1613 cm−1. HRMS calcd for C20H18N2O2 318.1367, found
318.1405. 2b: Colorless solid; mp 122.6–123.9°C; 1H NMR (CDCl3): l 3.71 (s, 4H, ArꢀCH2ꢀ), 5.09 (s, 2H,
CH2ꢁC), 7.18 (d, J=7.0, 2H, Ar), 7.27 (t, J=7.8, 2H, Ar), 7.42–7.48 (m, 6H, Ar), 7.62 (dd, J=0.9, 7.9, 2H, Ar),
8.06 (dd, J=1.4, 8.2, 4H, Ar). IR (KBr): 1615 cm−1. HRMS calcd for C30H22N2O2 442.1680, found 442.1704. 3b:
Colorless solid; mp 61.5–63.0°C; 1H NMR (CDCl3): l 1.50 (s, 3H, CH3ꢀC(ꢀOꢀ)), 3.16 (d, J=15.4, 1H, ArꢀCHꢀ),
3.22 (d, J=13.8, 1H, ArꢀCHꢀ), 3.36 (d, J=15.4, 1H, ArꢀCHꢀ), 3.53 (d, J=13.8, 1H, ArꢀCHꢀ), 6.92 (t, J=7.5,
1H, Ar), 6.95 (d, J=7.2, 1H, Ar), 7.22 (d, J=6.6, 1H, Ar), 7.30 (t, J=7.7, 1H, Ar), 7.43 (d, J=7.2, 1H, Ar), 7.48
(d, J=7.5, 1H, Ar), 7.61 (dd, J=1.2, 8.3, 1H, Ar), 7.69 (dd, J=1.1, 8.0, 1H, Ar), 7.84 (bs, 1H, NH), 8.10 (d,
J=7.0, 2H, Ar), 8.27 (d, J=8.0, 1H, Ar). IR (KBr): 1675, 1626 cm−1. HRMS calcd for C30H24N2O3 460.1786,