9078
C. Hu et al. / Tetrahedron 65 (2009) 9075–9080
d
7.94 (br s, 1H), 7.84–7.81 (m, 2H), 7.72–7.69 (m, 2H), 7.48 (s, 1H),
4.15. Compound 11g–II (P2[Phth)
7.23 (d, J¼8.4 Hz, 1H), 7.05 (d, J¼1.6 Hz, 1H), 7.00 (d, J¼8.4 Hz, 1H),
4.00 (t, J¼8.0 Hz, 2H), 3.13 (t, J¼8.0 Hz, 2H), 2.43 (s, 3H); 13C NMR
A red solid; yielded 60%; mp >250 ꢀC; IR (KBr) nmax: 3357, 1770,
(75 MHz, CDCl3)
d
168.4,134.5, 133.8,132.2, 128.7,127.6,123.7, 123.1,
1715, 1392, 1321, 1284, 1103, 717 cmꢂ1; 1H NMR (400 MHz, DMSO-
122.1, 118.4, 111.9, 110.7, 38.6, 24.4, 21.4; HRMS (ESI) m/z calcd for
C19H17N2O2 (MþH)þ 305.1285; found 305.1283.
d6)
d
11.69 (br s, 1H), 7.82–7.74 (m, 6H), 7.45 (s, 1H), 7.24 (t, J¼8.0 Hz,
1H), 3.77 (t, J¼6.8 Hz, 2H), 3.14 (t, J¼6.8 Hz, 2H); 13C NMR
(100 MHz, DMSO-d6) d 167.6, 142.5, 139.3, 134.3, 131.4, 129.5, 122.9,
4.10. Compound 11e–I (P2[(Boc)2)
122.0, 118.3, 116.9, 110.2, 39.5 (in solvent peaks), 25.9; HRMS (ESI)
m/z calcd for C18H14N3O4 (MþH)þ 336.0979; found 336.0973.
A white solid; yielded 56%; mp 158–160 ꢀC; IR (KBr) nmax: 3311,
2980, 1771, 1367, 1283, 1130, 1087, 936, 846, 717 cmꢂ1
;
1H NMR
4.16. Compound 11h–I (P2[(Boc)2)
(400 MHz, DMSO-d6)
d
10.93 (br s, 1H), 7.31 (dd, J¼8.8, 4.8 Hz, 1H),
7.22 (dd, J¼10, 2.4 Hz, 1H), 7.17 (d, J¼2.4 Hz, 1H), 6.89 (dt, J¼9.2,
2.4 Hz, 2H), 3.70 (t, J¼7.2 Hz, 2H), 2.87 (t, J¼8.0 Hz, 2H), 1.37 (s,
A pale yellow solid; yielded 16%; mp 184–188 ꢀC; IR (KBr) nmax
3299, 2984, 1773, 1366, 1139, 1100, 742 cmꢂ1 1H NMR (400 Hz,
CDCl3)
9.42 (br s, 1H), 7.36 (t, J¼4.4 Hz, 1H), 7.04 (s, 1H), 7.03 (s,
1H), 6.87 (d, J¼2.4 Hz, 1H), 4.04 (t, J¼6.4 Hz, 2H), 3.25 (t, J¼6.0 Hz,
2H), 1.29 (s, 18H); 13C NMR (100 MHz, CDCl3)
152.4 (2C), 138.2,
126.2, 125.0, 124.4, 121.9, 119.8, 111.9, 110.5, 81.9 (2C), 47.6, 27.7 (6C),
25.8; HRMS (ESI) m/z calcd for C20H27ClN2O4Na (MþNa)þ 417.1552;
found 417.1555.
:
;
18H); 13C NMR (100 MHz, DMSO-d6)
d
156.7 (d, J¼230 Hz), 152.0
d
(2C), 132.9, 127.5 (d, J¼9 Hz), 125.2, 112.3 (d, J¼10 Hz), 111.1 (d,
J¼4 Hz), 108.9 (d, J¼26 Hz), 102.7 (d, J¼22 Hz), 81.5 (2C), 46.6, 27.5
(6C), 24.4; HRMS (ESI) m/z calcd for C20H27FN2O4Na (MþNa)þ
401.1847; found 401.1841.
d
4.11. Compound 11e–II (P2[Phth)
4.17. Compound 11h–II (P2[Phth)
A yellow solid; yielded 49%; mp 122–124 ꢀC; IR (KBr) nmax: 3376,
1765, 1711, 1398, 1360, 1094, 1027, 991, 715 cmꢂ1
;
1H NMR
A yellow solid; yielded 23%; mp 220–222 ꢀC; IR (KBr) nmax: 3376,
(400 MHz, DMSO-d6)
d
10.91 (br s, 1H), 7.84–7.79 (m, 4H), 7.30 (dd,
1767, 1703, 1394, 1106, 716 cmꢂ1 1H NMR (400 MHz, DMSO-d6)
;
J¼8.8, 4.4 Hz, 1H), 7.26 (dd, J¼10.0, 2.4 Hz, 1H), 7.23 (d, J¼2.0 Hz,
d
11.17 (br s, 1H), 7.85–7.80 (m, 4H), 7.30 (dd, J¼7.6, 1.2 Hz, 1H), 7.20
1H), 6.88 (dt, J¼9.2, 2.4 Hz, 1H), 3.82 (t, J¼7.6 Hz, 2H), 2.98 (t,
(d, J¼2.4 Hz, 1H), 7.03 (t, J¼7.6 Hz, 1H), 6.99 (dd, J¼7.6, 1.2 Hz, 1H),
J¼7.6 Hz, 2H); 13C NMR (100 MHz, DMSO-d6)
d 167.8, 156.7 (d,
3.91 (t, J¼7.2 Hz, 2H), 3.23 (t, J¼7.2 Hz, 2H); 13C NMR (75 MHz,
J¼230 Hz), 134.3, 132.9, 131.6, 127.3 (d, J¼10 Hz), 125.1, 123.0, 112.4
(d, J¼10 Hz), 110.9 (d, J¼5 Hz), 109.1 (d, J¼26 Hz),102.6 (d, J¼23 Hz),
38.0, 23.7. HRMS (ESI) m/z calcd for C18H14FN2O2 (MþH)þ 309.1034;
found 309.1027.
DMSO-d6) d 167.8,137.9,134.4,131.6,125.3,124.6,123.5,123.0,121.8,
119.2, 110.8, 110.7, 39.5 (in solvent peaks), 24.9; HRMS (ESI) m/z
calcd for C18H14ClN2O2 (MþH)þ 325.0738; found 325.0730.
4.18. Compound 11i–I (P2[(Boc)2)
4.12. Compound 11f–I (P2[(Boc)2)
A white solid; yielded 52%; mp 115–116 ꢀC; IR (KBr) nmax: 3346,
A yellow solid; yielded 50%; mp 180–182 ꢀC; IR (KBr) nmax
3281, 2980, 1771, 1369, 1331, 1232, 1143, 1111, 1083, 742 cmꢂ1 1H
NMR (400 MHz, DMSO-d6)
:
2976, 1772, 1368, 1137, 1120, 1098, 740 cmꢂ1 1H NMR (400 MHz,
;
;
CDCl3)
d
8.00 (br s, 1H), 7.58 (d, J¼8.0 Hz, 1H), 7.35 (d, J¼8.0 Hz, 1H),
d
11.62 (br s, 1H), 8.48 (d, J¼2.0 Hz,
7.18 (dt, J¼8.0, 1.2 Hz, 1H), 7.10 (dt, J¼8.0, 1.6 Hz, 1H), 7.02 (d,
J¼2.0 Hz, 1H), 3.69 (t, J¼7.6 Hz, 2H), 2.77 (t, J¼7.6 Hz, 2H), 2.05–1.99
1H), 7.97 (dd, J¼8.8, 2.0 Hz, 1H), 7.50 (d, J¼8.8 Hz, 1H), 7.39 (s,
1H), 3.74 (t, J¼6.8 Hz, 2H), 2.99 (t, J¼6.8 Hz, 2H), 1.33 (s, 18H); 13C
(m, 2H), 1.48 (s, 18H); 13C NMR (75 Hz, CDCl3)
d 152.7 (2C), 136.3,
NMR (100 MHz, DMSO-d6)
d
152.0 (2C), 140.3, 139.4, 127.2, 126.7,
127.4, 121.9, 121.1, 119.1, 118.7, 115.8, 111.0, 82.1 (2C), 46.4, 29.3, 28.0
(6C), 22.4; HRMS (ESI) m/z calcd for C21H30N2O4Na (MþNa)þ
397.2098; found 397.2090.
116.4, 115.6, 114.1, 111.8, 81.5 (2C), 46.8, 27.4 (6C), 24.1; HRMS
(ESI) m/z calcd for C20H27N3O6Na (MþNa)þ 428.1792; found
428.1787.
4.19. Compound 11i–II (P2[Phth)
4.13. Compound 11f-II (P2[Phth)
A yellow solid; yielded 77%; mp 130–132 ꢀC [lit.,22 mp 131–132];
A yellow solid; yielded 63%; mp 228–230 ꢀC; IR (KBr) nmax: 3432,
1H NMR (400 MHz, CDCl3)
d 8.02 (br s, 1H), 7.84–7.81 (m, 2H), 7.72–
1768, 1708, 1398, 1327, 1122, 720 cmꢂ1; 1H NMR (400 MHz, DMSO-
7.69 (m, 2H), 7.60 (d, J¼8.0 Hz, 1H), 7.32 (d, J¼8.0 Hz, 1H), 7.17 (dt,
J¼8.0, 0.8 Hz, 1H), 7.11 (dt, J¼8.0, 1.2 Hz, 1H), 7.08 (d, J¼2.0 Hz, 1H),
3.81 (t, J¼7.2 Hz, 2H), 2.84 (t, J¼7.2 Hz, 2H), 2.18–2.10 (m, 2H); 13C
d6)
d
11.58 (br s, 1H), 8.51 (d, J¼2.0 Hz, 1H), 7.94 (dd, J¼8.8, 2.0 Hz,
1H), 7.82–7.79 (m, 4H), 7.48 (d, J¼8.8 Hz, 1H), 7.44 (d, J¼2.4 Hz, 1H),
3.86 (t, J¼7.2 Hz, 2H), 3.10 (t, J¼7.2 Hz, 2H); 13C NMR (400 MHz,
NMR (100 MHz, CDCl3) d 168.5,136.3,133.8,132.1,127.3,123.1,121.9,
DMSO-d6)
d
167.8, 140.2, 139.4, 134.3, 131.5, 127.1, 126.4, 123.0, 116.4,
121.5, 119.1, 118.8, 115.1, 111.0, 37.8, 28.5, 22.4; HRMS (ESI) m/z calcd
115.3, 113.9, 111.9, 38.2, 23.4; HRMS (ESI) m/z calcd for C18H17N4O4
(MþNH4)þ 353.1244; found 353.1248.
for C19H17N2O2 (MþH)þ 305.1285; found 305.1286.
4.20. Compound 13
4.14. Compound 11g–I (P2[(Boc)2)
A yellow solid; yielded 60%; mp 170–172 ꢀC; IR (KBr) nmax
3382, 3358, 1767, 1702, 1398, 1082, 718 cmꢂ1 1H NMR (400 MHz,
CDCl3) 8.09 (br s, 1H), 7.85–7.83 (m, 2H), 7.72–7.69 (m, 2H), 7.38
:
A yellow solid; yielded 50%; mp 186–188 ꢀC; IR (KBr) nmax: 3269,
;
2985, 1766, 1521, 1367, 1328, 1138, 1103, 787 cmꢂ1
;
1H NMR
d
(300 MHz, CDCl3)
d
10.97 (br s, 1H), 7.93 (d, J¼7.8 Hz, 1H), 7.92 (d,
(d, J¼8.8 Hz, 1H), 7.02 (d, J¼1.6 Hz, 1H), 6.86 (d, J¼8.8 Hz, 1H),
J¼7.8 Hz, 1H), 7.20 (t, J¼7.8 Hz, 1H), 6.99 (d, J¼2.4 Hz, 1H), 4.02 (t,
3.99 (t, J¼8.0 Hz, 2H), 3.97 (s, 3H), 3.92 (s, 3H), 3.10 (t, J¼8.0 Hz,
J¼5.4 Hz, 2H), 3.17 (t, J¼5.4 Hz, 2H), 1.22 (s, 18H); 13C NMR (75 MHz,
2H); 13C NMR (100 MHz, CDCl3)
d 168.3, 147.2, 134.5, 133.8, 132.2,
CDCl3)
d
152.5 (2C), 142.7, 139.8, 129.8, 119.8, 119.4, 118.4, 117.5,
130.8, 124.2, 123.1, 121.6, 113.8, 112.7, 108.4, 60.8, 57.5, 38.4, 24.5;
HRMS (ESI) m/z calcd for C20H19N2O4 (MþH)þ 351.1339; found
351.1338.
110.6, 82.2 (2C), 47.3, 27.6 (6C), 27.0. HRMS (ESI) m/z calcd for
C20H27N3O6Na (MþNa)þ 428.1792; found 428.1785.