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C.V. Yelamaggad, V.P. Tamilenthi / Tetrahedron 65 (2009) 6403–6409
4.5.1. Compound T-3
4.5.6. Compound T-8
Yield: 80%; a yellow solid [Found: C, 76.86; H, 4.93; N, 5.67.
C45H37N3O3 requires C, 77.23; H, 5.33; N, 6.00.]. IR (KBr pellet): nmax
in cmꢂ1 3054, 2928, 1616, and 1265. UV–vis: lmax¼304.9 nm,
Yield: 79%; a yellow solid [Found: C, 78.90; H, 6.61; N, 4.80.
C
55H57N3O3 requires C, 78.64; H, 6.84; N, 5.00.]. IR (KBr pellet): nmax
in cmꢂ1 3054, 2940, 1600, and 1265. UV–vis: lmax¼303.3 nm,
3
¼2.1ꢃ109 L molꢂ1 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d
13.87 (s, 1H,
3
. d 13.9 (s, 1H,
¼1.3ꢃ109 L molꢂ1 cmꢂ1 1H NMR (400 MHz, CDCl3):
OH), 8.49 (s, 1H, CH]N), 7.68 (d, J¼8.1 Hz, 4H, Ar), 7.63 (d, J¼8.2 Hz,
4H, Ar), 7.53 (d, J¼8.7 Hz, 4H, Ar), 7.24–7.20 (m, 3H, Ar), 7.02 (d,
J¼8.3 Hz, 4H, Ar), 6.95 (d, J¼8.7 Hz, 2H, Ar), 6.52–6.47 (m, 2H, Ar),
4.26–4.18 (m, 8H, 4ꢃOCH2), and 2.34–2.27 (m, 4H, 2ꢃCH2). 13C NMR
(100 MHz, CDCl3): 163.7, 162.9, 159.6, 159.5, 158, 145.3, 141.0, 133.2,
132.6, 131.4, 128.4, 127.1, 122, 119.1, 115.2, 113.2, 110.1, 107.4, 101.7,
64.5, 29.3, and 29.1. MS (FABþ): m/z calcd for C45H38N3O3 (Mþ1):
700.0; found: 700.2.
OH), 8.49 (s, 1H, CH]N), 7.68 (d, J¼8.3 Hz, 4H, Ar), 7.63 (d, J¼8.4 Hz,
4H, Ar), 7.51 (d, J¼8.7 Hz, 4H, Ar), 7.24–7.21 (m, 3H, Ar), 6.97 (d,
J¼8.3 Hz, 4H, Ar), 6.92 (d, J¼8.8 Hz, 2H, Ar), 6.49–6.45 (m, 2H, Ar),
4.06–4.01 (m, 8H, 4ꢃOCH2), and 1.89–1.56 (m, 24H, 12ꢃCH2). 13C
NMR (100 MHz, CDCl3): 163.8, 163.2, 159.8, 159.5, 158, 145.3, 141,
133.2, 132.6, 131.4, 128.4, 127.1, 122, 119.1, 115.2, 113.2, 110.1, 107.4,
101.7, 67.2, 29.7, 28.9, and 22.7. MS (FABþ): m/z calcd for
C55H57N3O3: 839.0; found: 839.1.
4.5.2. Compound T-4
4.5.7. Compound T-9
Yield: 81%; a yellow solid [Found: C, 77.60; H, 5.28; N, 5.71.
C47H41N3O3 requires C, 77.56; H, 5.63; N, 5.77.]; IR (KBr pellet): nmax
in cmꢂ1 3054, 2928, 1610, and 1265. UV–vis: lmax¼297.3 nm,
Yield: 79%; a yellow solid [Found: C, 78.37; H, 6.94; N, 5.03.
C57H61N3O3 requires C, 78.86; H, 7.08; N, 4.84.]. IR (KBr pellet): nmax
in cmꢂ1 3054, 2932, 1610, and 1265. UV–vis: lmax¼301.9 nm,
3
¼0.76ꢃ109 L molꢂ1 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d
13.92 (s,1H,
3
¼0.25ꢃ109 L molꢂ1 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d 13.91 (s, 1H,
OH), 8.49 (s, 1H, CH]N), 7.68 (d, J¼8.1 Hz, 4H, Ar), 7.63 (d, J¼8.2 Hz,
4H, Ar), 7.52 (d, J¼8.7 Hz, 4H, Ar), 7.22–7.20 (m, 3H, Ar), 6.98 (d,
J¼8.3 Hz, 4H, Ar), 6.92 (d, J¼8.7 Hz, 2H, Ar), 6.48–6.44 (m, 2H, Ar),
4.04–3.99 (m, 8H, 4ꢃOCH2), and 2.01–1.38 (m, 8H, 4ꢃCH2). MS
(FABþ): m/z calcd for C47H42N3O3 (Mþ1): 728.3; found: 728.7.
OH), 8.49 (s, 1H, CH]N), 7.68 (d, J¼8.3 Hz, 4H, Ar), 7.63 (d, J¼8.2 Hz,
4H, Ar), 7.52 (d, J¼8.7 Hz, 4H, Ar), 7.22–7.19 (m, 3H, Ar), 6.98 (d,
J¼8.3 Hz, 4H, Ar), 6.92 (d, J¼8.7 Hz, 2H, Ar), 6.48–6.44 (m, 2H, Ar),
4.02–3.96 (m, 8H, 4ꢃOCH2), and 1.84–1.38 (m, 28H, 14ꢃCH2). 13C
NMR (100 MHz, CDCl3): 163.8, 163.2, 159.8, 159.5, 158, 145.3, 141,
133.2, 132.6, 131.4, 128.4, 127.1, 122, 119.1, 115.2, 113.2, 110.1, 107.4,
101.7, 68.2, 29.4, 29.2, and 26.0. MS (FABþ): m/z calcd for
C57H61N3O3: 868.1; found: 868.1.
4.5.3. Compound T-5
Yield: 80%; a yellow solid [Found: C, 77.91; H, 6.31; N, 5.33.
C49H45N3O3 requires C, 77.86; H, 6.00; N, 5.56.]. IR (KBr pellet): nmax
in cmꢂ1 3054, 2942, 1606, and 1265; UV–vis: lmax¼294 nm,
4.5.8. Compound T-10
3
¼1.7ꢃ109 L molꢂ1 cmꢂ1
.
1H NMR (400 MHz, CDCl3):
d
13.9 (s, 1H,
Yield: 79%; a yellow solid [Found: C, 79.15; H, 7.26; N, 4.81.
C59H65N3O3 requires C, 79.07; H, 7.31; N, 4.69.]. IR (KBr pellet):
nmax in cmꢂ1 3054, 2854, 1605, and 1265. UV–vis: lmax¼299.3 nm,
OH), 8.49 (s, 1H, CH]N), 7.69 (d, J¼8.2 Hz, 4H, Ar), 7.64 (d, J¼8.3 Hz,
4H, Ar), 7.53 (d, J¼8.6 Hz, 4H, Ar), 7.24–7.17 (m, 3H, Ar), 6.96 (d,
J¼8.4 Hz, 4H, Ar), 6.92 (d, J¼8.7 Hz, 2H, Ar), 6.48–6.44 (m, 2H, Ar),
4.01–3.99 (m, 8H, 4ꢃOCH2), and 1.85–1.38 (m, 12H, 6ꢃCH2). 13C
NMR (100 MHz, CDCl3): 163.8, 163.2, 159.8, 159.5, 158, 145.3, 141,
133.2, 132.6, 131.4, 128.4, 127.1, 122, 119.1, 115.2, 113.2, 110.1, 107.4,
101.7, 68.2, 29.2, and 25.9. MS (FABþ): m/z calcd for C49H45N3O3:
755.3; found: 755.6.
3
¼0.9ꢃ109 L molꢂ1 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d 14.01 (s, 1H,
OH), 8.46 (s, 1H, CH]N), 7.69 (d, J¼8.0 Hz, 4H, Ar), 7.64 (d,
J¼8.0 Hz, 4H, Ar), 7.53 (d, J¼8.0 Hz, 4H, Ar), 7.28–7.26 (m, 3H, Ar),
6.99 (d, J¼8.3 Hz, 4H, Ar), 6.92 (d, J¼8.7 Hz, 2H, Ar), 6.52–6.50 (m,
2H, Ar), 4.01–3.99 (m, 8H, 4ꢃOCH2), and 1.82–1.35 (m, 32H,
16ꢃCH2). MS (FABþ): m/z calcd for C59H65N3O3: 896.2; found:
896.4.
4.5.4. Compound T-6
Yield: 77%; a yellow solid [Found: C, 78.26; H, 6.85; N, 5.13.
C51H49N3O3 requires C, 78.14; H, 6.30; N, 5.36.]. IR (KBr pellet): nmax
in cmꢂ1 3054, 2940, 1625, and 1265. UV–vis: lmax¼293.9 nm,
4.5.9. Compound T-11
Yield: 79%; a yellow solid [Found: C, 79.33; H, 7.49; N, 4.76.
C61H69N3O3 requires C, 79.27; H, 7.53; N, 4.55.]. IR (KBr pellet): nmax
in cmꢂ1 3054, 2922, 1605, and 1265. UV–vis: lmax¼301.2 nm,
3
¼1.3ꢃ109 L molꢂ1 cmꢂ1
. d 13.9 (s, 1H,
1H NMR (400 MHz, CDCl3):
OH), 8.49 (s, 1H, CH]N), 7.68 (d, J¼8.3 Hz, 4H, Ar), 7.63 (d, J¼8.4 Hz,
4H, Ar), 7.52 (d, J¼8.7 Hz, 4H, Ar), 7.22–7.20 (m, 3H, Ar), 6.99 (d,
J¼8.3 Hz, 4H, Ar), 6.92 (d, J¼8.7 Hz, 2H, Ar), 6.49–6.44 (m, 2H, Ar),
4.01–3.99 (m, 8H, 4ꢃOCH2), and 1.85–1.38 (m, 16H, 8ꢃCH2). 13C
NMR (100 MHz, CDCl3): 163.8, 163.2, 159.8, 159.5, 158.0, 145.3, 141,
133.2, 132.6, 131.4, 128.4, 127.1, 122, 119.1, 115.2, 113.2, 110.1, 107.4,
101.7, 68.1, 29.1, and 25.9. MS (FABþ): m/z calcd for C51H49N3O3:
782.4; found: 782.8.
3
¼1.14ꢃ109 L molꢂ1 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d 13.91 (s, 1H,
OH), 8.42 (s, 1H, CH]N), 7.61 (d, J¼8.2 Hz, 4H, Ar), 7.56 (d, J¼8.3 Hz,
4H, Ar), 7.45 (d, J¼8.6 Hz, 4H, Ar), 7.19–7.13 (m, 3H, Ar), 6.92 (d,
J¼8.6 Hz, 4H, Ar), 6.84 (d, J¼8.7 Hz, 2H, Ar), 6.40–6.38 (m, 2H, Ar),
3.94–3.67 (m, 8H, 4ꢃOCH2), and 1.78–1.25 (m, 36H, 18ꢃCH2). MS
(FABþ): m/z calcd for C61H69N3O3: 924.2; found: 924.5.
4.5.10. Compound T-12
Yield: 78%; a yellow solid [Found: C, 79.28; H, 7.27; N, 4.81.
C63H73N3O3 requires C, 79.46; H, 7.73; N, 4.41.]. IR (KBr pellet): nmax
in cmꢂ1 3054, 2918, 1603, and 1265. UV–vis: lmax¼302.1 nm,
4.5.5. Compound T-7
Yield: 81%; a yellow solid [Found: C, 78.31; H, 6.37; N, 5.29.
C53H53N3O3 requires C, 78.39; H, 6.58; N, 5.17.]. IR (KBr pellet): nmax
in cmꢂ1 3054, 2937, 1605, and 1265. UV–vis: lmax¼293.9 nm,
3
¼1.3ꢃ109 L molꢂ1 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d 13.91 (s, 1H,
OH), 8.41 (s, 1H, CH]N), 7.67 (d, J¼8.4 Hz, 4H, Ar), 7.63 (d, J¼8.4 Hz,
4H, Ar), 7.53 (d, J¼8.8 Hz, 4H, Ar), 7.22–7.20 (m, 3H, Ar), 6.99 (d,
J¼8.4 Hz, 4H, Ar), 6.92 (d, J¼8.8 Hz, 2H, Ar), 6.48–6.44 (m, 2H, Ar),
4.04–3.95 (m, 8H, 4ꢃOCH2), and 1.85–1.38 (m, 40H, 20ꢃCH2). MS
(FABþ): m/z calcd for C63H73N3O3: 952.2; found: 952.4.
3
¼2.1ꢃ109 L molꢂ1 cmꢂ1. 1H NMR (400 MHz, CDCl3):
d 14.01 (s, 1H,
OH), 8.49 (s, 1H, CH]N), 7.68 (d, J¼8.1 Hz, 4H, Ar),7.63 (d, J¼8.2 Hz,
4H, Ar), 7.52 (d, J¼8.6 Hz, 4H, Ar), 7. 23–7.16 (m, 3H, Ar), 6.98 (d,
J¼8.3 Hz, 4H, Ar), 6.92 (d, J¼8.7 Hz, 2H, Ar), 6.48–6.45 (m, 2H, Ar),
4.10–3.97 (m, 8H, 4ꢃOCH2), and 1.83–1.25 (m, 20H, 10ꢃCH2). 13C
NMR (100 MHz, CDCl3): 163.8, 163.2, 159.8, 159.5, 158, 145.3, 141,
133.2, 132.6, 131.4, 128.4, 127.1, 122, 119.1, 115.2, 113.2, 110.1, 107.4,
101.7, 68.1, 29.2, and 26. MS (FABþ): m/z calcd for C53H53N3O3:
812.0; found: 812.7.
Acknowledgements
We thank Dr. S. Krishna Prasad for helpful discussions.