1
3
H-6 and H-8), 7.77-7.8 (m, 1H, H-5), 12.43 (br s, 1H, OH); C-NMR (68 MHz, DMSO-d ) δ
6
+
1
1
10.4, 115.5, 123.7, 130.0, 142.5, 159.6; MS (EI) m/z 135 (M ); HR-MS. Calcd for C H N O:
6
5 3
35.0433 Found: 135.0428.
1
0. All new compounds are fully characterized. Data for selected compounds; 4a: mp 166-168 °C (colorless
-
1
1
crystals from hex-CH Cl ); IR (KBr, cm ) 1666; H-NMR (270 MHz, CDCl ) δ 5.30 (s, 2H,
2
2
3
CH ), 6.86 (t, 1H, J = 6.9 Hz, H-6), 7.19 (d, 1H, J = 9.2 Hz, H-8), 7.34-7.37 (m, 5H, Ph), 7.46
2
1
3
(
dd, 1H, J = 9.2 Hz, J = 6.9 Hz, H-7), 8.22 (d, 1H, J = 6.9 Hz, H-5); C-NMR (68 MHz, CDCl )
3
δ 52.6, 108.5, 112.5, 125.6, 127.7, 128.6, 129.0, 133.9, 134.1, 138.5, 154.1; MS (EI) m/z 225
+
+
(
M ) 91 (PhCH ); Anal. Calcd for C H N O 0.5H O: C, 66.65; H, 5.16; N, 17.94. Found: C,
•
2
13 11
3
2
-
1
ꢀ
66.51; H,5.19; N, 17.88. 5a: mp 145-147 °C (colorless crystals from hex-CH Cl ); IR (KBr, cm )
2 2
1
1
702 (C=O); H-NMR (270 MHz, CDCl ) δ 5.17 (s, 2H, CH ), 6.45 (t, 1H, J = 6.9 Hz, H-6), 7.06
3 2
(
d, 1H, J = 6.9 Hz, H-8), 7.09 (t, 1H, J = 6.9 Hz, H-7), 7.26-7.42 (m, 5H, aromatic), 7.77 (d, 1H,
1
3
J = 6.9 Hz, H-5); C-NMR (68 MHz, CDCl ) δ 49.7, 110.5, 115.4, 123.7, 128.0, 128.3, 128.7,
3
+
+
1
6
29.8, 135.8, 141.6, 148.9; MS (EI) m/z 225 (M ), 91(PhCH ); Anal. Calcd for C H N O: C,
2 13 11 3
9.32; H, 4.92; N, 18.65. Found: C, 69.18; H, 4.97; N, 18.77. 6a: mp 127-129 °C (colorless
-
1
1
crystals from hex-PhH); IR (KBr, cm ) 1722, 1684; H-NMR (270 MHz, CDCl ) δ 3.49 (s, 3H,
3
Me), 3.78 (s, 3H, Me), 3.87 (s, 3H, Me), 3.93 (s, 3H, Me), 4,51 (d, 1H, J = 16 Hz, PhCH ), 5.72
2
(
d, 1H, J = 16 Hz, PhCH ), 6.57 (d, 1H, J = 8.3 Hz), 6.93 (dd, 1H, J = 8.3 Hz, J = 5 Hz), 7.26-
2
7
.36 (m, 5H, Ph), 7.55 (dd, 1H, J = 8.3 Hz, J = 5 Hz), 8.29 (d, 1H, J = 5 Hz); 13C-NMR (68
MHz, CDCl ) δ 53.2, 53.3, 56.7, 104.6, 109.0, 118.0, 123.4, 127.6, 128.2, 128.4, 136.2, 137.9,
3
+
1
45.8, 147.8, 151.3, 156.4, 157.4, 159.9, 161.9, 163.4, 165.0; MS (CI) m/z 510 (M + 1); Anal.
Calcd for C H N O : C, 58.94; H, 4.55; N, 8.25. Found: C, 59.10; H, 4.46; N, 8.22.
2
5 23 3 9
1
4
1
1. X-Ray crystallographic data for 4a: C H N O, M = 225.09, colorless prismatic, orthorhombic,
13 11 3
space group Pccn (alt. setting No. 56), a = 12.356 (3) Å, b = 14.074 (3) Å, c = 13.102 (3) Å, α =
3
-1
9
0.00°, β = 90.00°, γ = 90.00°, V = 2278 (1) Å , Z = 4, Dc 0.71 g/cm , F(000) = 360.00, µ(Cu
-
1
Kα) = 5.03 cm , graphite monochromated CuKα (λ = 1.54178 Å), T = 14 °C. Final discrepancy
factor: R = 0.052 and Rw = 0.058.
1
1
2. H. Barnighausen, F. Jellinek, J. Munnik, and A. Vos, Acta. Crystallogr., 1963, 16, 471.
1
4
2. X-Ray crystallographic data for 6a: C H N O, M = 509.47, colorless plates, triclinic, space
2
5
23
3
group P1 (alt. setting No. 2), a = 10.362 (8) Å, b = 15.226 (9) Å, c = 8.615 (8) Å, α = 90.33 (6)°, β
3
-1
=
109.04 (6)°, γ = 75.49 (5)°, V = 1239 (1) Å , Z = 2, Dc 1.365 g/cm , F(000) = 820.00, µ(Mo
-
1
Kα) = 0.77 cm , graphite monochromated MoKα (λ = 0.71069 Å), T = 23 °C. Final discrepancy
factor: R = 0.110 and Rw = 0.116.
1
4. The structures of 4a and 6a were solved by the direct method (SHELEX-86).