J.R.A. Cottam, P.J. Steel / Tetrahedron 64 (2008) 2915e2923
2921
(4H, H2, H6), 2.35 (4H, H8), 1.64 (4H, H9), 1.56 (2H, H10).
4.3.22. Compound 12Z
13C NMR (75 MHz, CDCl3): d 156.80, 150.45, 145.39,
139.96, 139.56, 139.27, 130.32, 128.87, 128.42, 127.72, 127.39,
120.78, 45.78, 37.36, 26.32, 22.85. ESI-MS: found
MHþ¼525.2309; C34H29N4O2 requires MHþ¼525.2291.
Method B from 5Z and 7a. White solid. Yield 45%. Mp
98e99.5 ꢀC. Anal. Found: C, 79.95; H, 6.72; N, 6.22. Calcd
for C30H30N2O2: C, 79.97; H, 6.71; N, 6.22. 1H NMR
(300 MHz, CHCl3): d 8.56 (2H, H60), 7.69 (2H, H40), 7.52
(2H, H30), 7.20 (2H, H50), 7.16 (4H, H3, H5), 6.89 (4H, H2,
H6), 5.16 (4H, CH2), 2.19 (4H, H8), 1.50 (6H, H9, H10).
13C NMR (75 MHz, CDCl3): d 157.27, 155.91, 148.60,
141.54, 137.30, 128.16, 122.67, 121.43, 114.35, 70.19, 45.05,
37.33, 26.37, 22.87. ESI-MS: found MHþ¼451.2364;
C30H31N2O2 requires MHþ¼451.2386.
4.3.18. Compound 11AP
Method A from 5AP and 6d. Yellow crystalline solid. Yield
60%. Mp 136.5 ꢀC. Anal. Found: C, 76.77; H, 5.00; N, 9.08.
Calcd for C36H27N4O2$1/3H2O$CH3COCH3: C, 76.70; H,
5.39; N, 9.17. 1H NMR (500 MHz, CHCl3): d 8.69 (2H,
H30), 8.07 (2H, H80), 7.80 (2H, H50), 7.68 (2H, H60), 7.63
(2H, H70), 7.34 (2H, H300, H500), 7.27e7.14 (11H, H2, H3,
H5, H6, H200, H400, H600), 2.28 (3H, H8). 13C NMR
(75 MHz, CDCl3): d 156.77, 150.93, 148.72, 145.94, 139.91,
139.09, 130.45, 129.97, 128.81, 128.69, 128.04, 127.73,
127.54, 126.22, 120.49, 104.70, 51.13, 22.78. ESI-MS: found
MHþ¼547.2112; C36H27N4O2 requires MHþ¼547.2134.
4.3.23. Compound 12AP
1
Method B from 5AP and 7a. Brown oil. Yield 98.1%. H
NMR (500 MHz, CHCl3): d 8.54 (2H, H60), 7.65 (2H, H40),
7.50 (2H, H30), 7.22 (2H, H50), 7.15 (1H, H400), 7.08 (4H,
H200, H300, H500, H600), 7.00 (4H, H3, H5), 6.88 (4H, H2,
H6), 5.16 (4H, CH2), 2.12 (3H, H8). 13C NMR (75 MHz,
CDCl3): d 157.06, 156.22, 149.21, 148.83, 141.70, 136.62,
129.50, 128.33, 127.58, 125.64, 122.37, 121.05, 113.77, 70.27,
51.01, 30.41. ESI-MS: found MHþ¼473.2249; C32H29N2O2
requires MHþ¼473.2229.
4.3.19. Compound 11P
Method A from 5P and 6d. Yellow solid. Yield 39%. Mp
174e175 ꢀC. Anal. Found: C, 78.51; H, 5.82; N, 8.54. Calcd
1
for C40H34N4O2$CH3COCH3: C, 78.16; H, 6.10; N, 8.48. H
4.3.24. Compound 12P
Method B from 5P and 7a. White crystalline solid. Yield
80%. Mp 171 ꢀC. Anal. Found: C, 81.73; H, 7.03; N, 5.28.
NMR (500 MHz, CHCl3): d 8.67 (2H, H30), 8.07 (2H, H80),
7.79 (2H, H50), 7.66 (2H, H60), 7.62 (2H, H70), 7.32 (4H,
H3, H5), 7.20 (4H, H200, H300, H500, H600), 7.18 (2H, H2,
H6), 1.72 (12H, H8). 13C NMR (75 MHz, CDCl3): d 150.54,
147.79, 147.60, 140.09, 139.34, 139.05, 130.40, 128.76,
128.07, 127.76, 127.46, 126.40, 120.48, 104.70, 42.34,
30.77. ESI-MS: found MHþ¼603.2753; C40H35N4O2 requires
MHþ¼603.2760.
1
Calcd for C36H36N2O2: C, 81.79; H, 6.86; N, 5.30. H NMR
(500 MHz, CHCl3): d 8.58 (2H, H60), 7.72 (2H, H40), 7.69
(2H, H30), 7.54 (2H, H50), 7.15 (4H, H3, H5), 7.09 (4H,
H200, H300, H500, H600), 6.88 (4H, H2, H6), 5.18 (4H, CH2),
1.63 (12H, H8). 13C NMR (75 MHz, CDCl3): d 157.45,
156.18, 149.02, 147.73, 143.41, 136.85, 127.82, 126.17, 122.52,
121.23, 114.07, 70.49, 41.83, 30.84. ESI-MS: found
MHþ¼529.2855; C36H37N2O2 requires MHþ¼529.2855.
4.3.20. Compound 11M
Method A from 5M and 6d. Orange solid. Yield 78%. Mp
143e144 ꢀC. Anal. Found: C, 79.68; H, 5.81; N, 9.05. Calcd
for C40H34N4O2: C, 79.71; H, 5.69; N, 9.30. 1H NMR
(500 MHz, CHCl3): d 8.61 (2H, H30), 8.02 (2H, H80), 7.73
(2H, H50), 7.62 (2H, H60), 7.57 (2H, H70), 7.29 (4H, H3,
H5), 7.25 (1H, H500), 7.18 (1H, H200), 716 (2H, H400, H600),
7.14 (4H, H2, H6), 1.71 (12H, H8). 13C NMR (75 MHz,
CDCl3): d 156.83, 150.47, 149.98, 147.72, 141.98, 139.92,
139.47, 139.16, 130.26, 128.84, 127.96, 127.63, 127.31,
125.60, 124.13, 120.47, 42.81, 30.82. ESI-MS: found
Mþ¼602.2681; C40H34N4O2 requires Mþ¼602.2682.
4.3.25. Compound 12M
Method B from 5M and 7a. White crystalline solid. Yield
84%. Mp 81e82 ꢀC. Anal. Found: C, 80.64; H, 7.21; N,
5.28. Calcd for C36H36N2O2$1/2H2O: C, 80.42; H, 6.94; N,
1
5.21. H NMR (500 MHz, CHCl3): d 8.56 (2H, H60), 7.66
(2H, H40), 7.51 (2H, H30), 7.18 (2H, H50), 7.17 (1H, H500),
7.10 (4H, H3, H5), 7.08 (1H, H200), 7.01 (2H, H400, H600),
6.86 (4H, H2, H6), 5.17 (4H, CH2), 1.60 (12H, H8). 13C
NMR (75 MHz, CDCl3): d 157.39, 156.08, 150.14, 149.03,
143.41, 136.71, 127.73, 127.33, 125.14, 123.97, 122.45, 121.17,
114.00, 70.48, 42.32, 30.81. ESI-MS: found MHþ¼529.2876;
C36H37N2O2 requires MHþ¼529.2855.
4.3.21. Compound 12A
Method B from 5A and 7a. White solid. Yield 26%. Mp
71e72 ꢀC. Anal. Found: C, 78.73; H, 6.51; N, 6.85. Calcd
for C27H26N2O2: C, 79.00; H, 6.38; N, 6.82. 1H NMR
(300 MHz, CHCl3): d 8.59 (2H, H60), 7.72 (2H, H40), 7.69
(2H, H30), 7.22 (2H, H50), 7.15 (4H, H3, H5), 6.88 (4H, H2,
H6), 5.18 (4H, CH2), 1.63 (6H, H8). 13C NMR (75 MHz,
CDCl3): d 157.46, 156.22, 149.11, 143.52, 136.79, 127.77,
122.52, 121.21, 114.12, 70.56, 41.68, 30.98. ESI-MS: found
MHþ¼411.2076; C27H27N2O2 requires MHþ¼411.2073.
4.3.26. Compound 13A
Method B from 5A and 7b. Yellow solid. Yield 53%. Mp
127e128.5 ꢀC. Anal. Found: C, 78.74; H, 6.43; N, 6.79. Calcd
for C27H26N2O2: C, 79.00; H, 6.38; N, 6.82. 1H NMR
(300 MHz, CHCl3): d 8.67 (2H, H20), 8.58 (2H, H60), 7.77
(2H, H40), 7.31 (2H, H50), 7.16 (4H, H3, H5), 6.88 (4H, H2,
H6), 5.04 (4H, CH2), 1.64 (6H, H8). 13C NMR (75 MHz,
CDCl3): d 156.20, 149.22, 148.83, 143.72, 135.36, 132.73,