M. Hosseini-Sarvari / Tetrahedron 64 (2008) 5459–5466
5465
3
3
(250 MHz, CDCl3): 1.13 (3H, t, JHH 7.0 Hz, –OCH2Me), 1.27 (3H, t, JHH
6.9 Hz, –OCH2Me), 3.77 (3H, s, PhOMe), 3.73–3.77 (1H, m,
–OCH2CH3), 3.78–3.87 (1H, m, –OCH2CH3), 4.07–4.13 (2H, m,
–OCH2CH3), 6.65 (1H, d, JHP 25 Hz, CHP), 5.33 (1H, br s, –NH), 6.80–
6.93 (5H, m, ArH), 7.13 (1H, t, J 7.4 Hz, ArH), 7.36 (2H, d, J 7.1 Hz,
(62.9 MHz, CDCl3): 16.1 (d, JCP 5.7 Hz, OCH2CH3), 16.3 (d, JCP
5.7 Hz, OCH2CH3), 55.0, 55.1 (JCP 152.9 Hz, CHP), 61.9 (d, 2JCP 6.9 Hz,
OCH2CH3), 63.4 (d, 2JCP 6.9 Hz, OCH2CH3), 101.2, 105.8, 106.4, 113.2,
127.5, 128.9, 129.9, 147.7, 157.5, 159.1; 31P NMR (202 MHz, CDCl3/
H3PO4):
d
20.42; m/z 365 (Mþ).
3
ArH); dC (62.9 MHz, CDCl3): 16.2 (d, JCP 5.7 Hz, OCH2CH3), 16.4 (d,
2
3JCP 5.7 Hz, OCH2CH3), 54.9 (d, 1JCP 153 Hz, CHP), 55.2, 63.2 (d, JCP
2.2.24. Compound 3x
7.4 Hz, OCH2CH3), 63.6 (d, 2JCP 7.1 Hz, OCH2CH3), 112.7, 114.2, 116.2,
White solid, mp 75 ꢀC. Found: C, 59.16; H, 6.62. C18H24NO5P
requires: C, 59.17; H, 6.62%. Rf (AcOEt/hexane 20:80) 0.25; nmax
(KBr): 3352 (–OH), 3303 (–NH), 1231 (P]O), 1100 (P–O–Et); dH
(250 MHz, CDCl3): 1.18 (3H, t, JHH 7.0 Hz, –OCH2Me), 1.28 (3H, t, JHH
7.0 Hz, –OCH2Me), 3.65 (3H, s, PhOMe), 3.70–3.73 (1H, m,
–OCH2CH3), 3.84–3.95 (1H, m, –OCH2CH3), 4.19–4.25 (2H, m,
–OCH2CH3), 4.83 (1H, d, JHP 24.6 Hz, CHP), 5.12 (1H, br s, –NH),
6.48–6.56 (3H, m, ArH), 6.64 (2H, d, J 8.6 Hz, ArH), 6.79 (1H, d, J
7.4 Hz, ArH), 7.34 (2H, d, J 8.6 Hz, ArH), 7.52 (1H, br s, OH); dC
118.2, 119.2, 126.4, 128.9, 130.0, 146.8, 159.5; 31P NMR (202 MHz,
CDCl3/H3PO4):
d
19.62; m/z 374 (Mþ).
2.2.19. Compound 3s12
White solid, mp 105 ꢀC (lit. 108–109 ꢀC); dH (250 MHz, CDCl3):
0.93 (3H, t, JHH 7.0 Hz, –OCH2Me), 1.02 (3H, t, JHH 7.1 Hz, –OCH2Me),
3.54 (3H, s, PhOMe), 3.51–3.54 (1H, m, –OCH2CH3), 3.58–3.69 (1H, m,
–OCH2CH3), 3.88–3.93 (2H, m, –OCH2CH3), 4.45 (1H, d, JHP 23.8 Hz,
CHP), 4.96 (1H, br s, –NH), 6.28 (2H, d, J 8.5 Hz, ArH), 6.66 (2H, d, J
8.3 Hz, ArH), 6.95 (2H, d, J 8.8 Hz, ArH), 7.13 (2H, d, J 8.8 Hz, ArH).
3
3
(62.9 MHz, CDCl3): 16.1 (d, JCP 5.7 Hz, OCH2CH3), 16.3 (d, JCP
2
5.7 Hz, OCH2CH3), 55.2 (d, JCP 155.5 Hz, CHP), 55.4, 63.6 (d, JCP
6.9 Hz, OCH2CH3), 64.0 (d, 2JCP 6.9 Hz, OCH2CH3), 112.0, 113.5, 114.3,
2.2.20. Compound 3t
118.2, 119.8, 127.3, 129.2, 134.8, 145.2, 159.1; 31P NMR (202 MHz,
White solid, mp 98 ꢀC. Found: C, 50.45; H, 5.40. C18H23BrNO4P
requires: C, 50.48; H, 5.41%. Rf (AcOEt/hexane 20:80) 0.31; nmax
(KBr): 3323 (–NH), 1236 (P]O), 1100 (P–O–Et); dH (250 MHz,
CDCl3): 1.03 (3H, t, JHH 7.0 Hz, –OCH2Me), 1.15 (3H, t, JHH 6.8 Hz,
–OCH2Me), 3.64 (s, 3H, PhOMe), 3.56–3.61 (1H, m, –OCH2CH3),
3.82–3.86 (1H, m, –OCH2CH3), 3.98–4.07 (2H, m, –OCH2CH3), 4.59
(1H, d, JHP 23.9 Hz, CHP), 5.20 (1H, br s, –NH), 6.43 (1H, s, ArH),
6.64–6.81 (5H, m, ArH), 7.29 (2H, d, J 8.7 Hz, ArH); dC3(62.9 MHz,
CDCl3/H3PO4): d
21.0; m/z 365 (Mþ).
2.2.25. Compound 3y27a
White solid, mp 95 ꢀC (lit. 100–102 ꢀC); dH (250 MHz, CDCl3):
0.97 (3H, t, JHH 7.0 Hz, –OCH2Me), 1.11 (3H, t, JHH 7.0 Hz, –OCH2Me),
1.99 (3H, s, PhMe), 3.51 (3H, s, PhOMe), 3.52–3.57 (1H, m,
–OCH2CH3), 3.77–3.80 (1H, m, –OCH2CH3), 3.92–3.99 (1H, m, 2H,
–OCH2CH3), 4.58 (d, 1H, JHP 23.8 Hz, CHP), 5.35 (br s, –NH), 6.41 (2H,
d, J 7.5 Hz, ArH), 7.67 (2H, d, J 7.2 Hz, ArH), 6.74 (2H, d, J 8.2 Hz, ArH),
7.26 (2H, d, J 8.5 Hz, ArH).
3
CDCl3): 16.2 (d, JCP 5.7 Hz, OCH2CH3), 16.5 (d, JCP 5.7 Hz,
OCH2CH3), 54.9 (d, JCP 153 Hz, CHP), 55.3, 63.2, (d, JCP 7.1 Hz,
2
2
OCH2CH3), 64.4 (d, JCP 7.0 Hz, OCH2CH3), 112.1, 114.0, 116.7, 120.7,
122.9, 127.2, 129.0, 130.3, 147.9, 159.3; 31P NMR (202 MHz, CDCl3/
2.2.26. Compound 3z
H3PO4):
d
20.52; m/z 428 (Mþ).
White solid, mp 86 ꢀC. Found: C, 62.79; H, 7.20. C19H26NO4P re-
quires: C, 62.80; H, 7.21%. Rf (AcOEt/hexane 20:80) 0.33; nmax (KBr):
3321 (–NH), 1230 (P]O), 1100 (P–O–Et); dH (250 MHz, CDCl3): 1.01
(3H, t, JHH 7.0 Hz, –OCH2Me), 1.13 (3H, t, JHH 7.0 Hz, –OCH2Me), 2.1
(3H, s, PhMe), 3.61 (3H, s, PhOMe), 3.51–3.58 (1H, m, –OCH2CH3),
3.78–3.85 (1H, m, –OCH2CH3), 3.95–4.04 (2H, m, –OCH2CH3), 4.63
(1H, d, JHP 23.9 Hz, CHP), 5.75 (1H, br s, –NH), 6.28–6.40 (3H, m, ArH),
6.75 (2H, d, J 8.4 Hz, ArH), 6.86 (1H, t, J 7.7 Hz, ArH), 7.30 (2H, d, J
2.2.21. Compound 3u
White solid, mp 51 ꢀC. Found: C, 50.45; H, 5.40. C18H23BrNO4P
requires: C, 50.48; H, 5.41%. Rf (AcOEt/hexane 20:80) 0.32; nmax
(KBr): 3320 (–NH), 1231 (P]O), 1106 (P–O–Et); dH (250 MHz,
CDCl3): 1.11 (3H, t, JHH 7.0 Hz, –OCH2Me), 1.22 (3H, t, JHH 7.0 Hz,
–OCH2Me), 3.64 (3H, s, PhOMe), 3.66–3.67 (1H, m, –OCH2CH3),
3.75–3.77 (1H, m, –OCH2CH3), 3.94–4.07 (2H, m, –OCH2CH3), 4.70
(1H, d, JHP 23.8 Hz, CHP), 5.40 (1H, br s, –NH), 6.41 (1H, d, J 7.0 Hz,
ArH), 6.49 (1H, t, J 7.6 Hz, ArH), 7.82 (2H, d, J 8.6 Hz, ArH), 6.94 (1H,
t, J 7.8 Hz, ArH), 7.28–7.36 (3H, m, ArH); dC (62.9 MHz, CDCl3): 16.2
(d, 3JCP 5.7 Hz, OCH2CH3), 16.4 (d, 3JCP 5.7 Hz, OCH2CH3), 55.1, 55.3
3
8.4 Hz, ArH); dC (62.9 MHz, CDCl3): 15.2 (d, JCP 5.7 Hz, OCH2CH3),
15.4 (d, 3JCP 5.7 Hz, OCH2CH3), 54.0, 54.1 (d, JCP 152.9 Hz, CHP), 62.0
(d, 2JCP 7.0 Hz, OCH2CH3), 62.2 (d, 2JCP 6.9 Hz, OCH2CH3), 109.8, 112.6,
112.9, 118.1, 126.7, 127.9, 128.0, 137.7, 145.5, 158.2; 31P NMR (202 MHz,
CDCl3/H3PO4):
d
22.82; m/z 363 (Mþ).
2
2
(d, JCP 152.7 Hz, CHP), 63.5 (d, JCP 7.1 Hz, OCH2CH3), 63.7 (d, JCP
7.1 Hz, OCH2CH3), 110.5, 112.7, 113.6, 118.8, 126.7, 128.3, 128.8,
2.2.27. Compound 3aa34,35
132.4, 143.1, 159.4; 31P NMR (202 MHz, CDCl3/H3PO4):
428 (Mþ).
d
19.73; m/z
White solid, mp 65 ꢀC (lit. 67–69 ꢀC); dH (259 MHz, CDCl3): 0.96
(3H, t, JHH 7.0 Hz, –OCH2Me), 1.13 (3H, t, JHH 7.1 Hz, –OCH2Me), 2.43
(3H, s, PhMe), 3.57 (3H, s, PhOMe), 3.59–3.66 (1H, m, –OCH2CH3),
3.70–3.79 (1H, m, –OCH2CH3), 3.86–3.92 (2H, m, –OCH2CH3), 4.58
(1H, d, JHP 23.7 Hz, CHP), 4.85 (1H, br s, –NH), 6.24 (1H, d, J 8.0 Hz,
ArH), 6.52 (1H, t, J 7.3 Hz, ArH), 6.69 (2H, d, J 8.5 Hz, ArH), 6.77 (1H, t,
J 7.5 Hz, ArH), 6.89 (1H, d, J 7.1 Hz, ArH), 7.18 (2H, d, J 8.5 Hz, ArH).
2.2.22. Compound 3v33a,b
White solid, mp 52 ꢀC (lit. 54–55 ꢀC); dH (250 MHz, CDCl3): 1.07
(3H, t, JHH 7.0 Hz, –OCH2Me), 1.22 (3H, t, JHH 7.0 Hz, –OCH2Me), 3.68
(3H, s, PhOMe), 3.63–3.64 (1H, m, –OCH2CH3), 3.70–3.90 (1H, m,
–OCH2CH3), 4.03–4.10 (2H, m, –OCH2CH3), 5.70 (1H, br s, –NH), 6.51
(2H, d, J 8.8 Hz, ArH), 6.76 (2H, d, J 8.8 Hz, ArH), 6.82 (2H, d, J 8.3 Hz,
ArH), 7.34 (2H, d, J 8.5 Hz, ArH).
2.2.28. Compound 3ab14,28
White solid, mp 118 ꢀC (lit. 119 ꢀC); dH (250 MHz, CDCl3): 1.09
(3H, t, JHH 7.0 Hz, –OCH2Me), 1.27 (3H, t, JHH 7.0 Hz, –OCH2Me), 3.40
(6H, s, PhOMe), 3.62–3.70 (1H, m, –OCH2CH3), 3.87–3.92 (1H, m,
–OCH2CH3), 4.03–4.12 (2H, m, –OCH2CH3), 4.62 (1H, d, JHP 24.2 Hz,
CHP), 5.45 (1H, br s, –NH), 6.51 (2H, d, J 7.5 Hz, ArH), 6.67 (2H, d, J
7.2 Hz, ArH), 6.96 (2H, d, J 8.5 Hz, ArH), 7.20 (2H, d, J 8.5 Hz, ArH).
2.2.23. Compound 3w
White solid, mp 96 ꢀC. Found: C, 59.15; H, 6.60. C18H24NO5P
requires: C, 59.17; H, 6.62%. Rf (AcOEt/hexane 20:80) 0.28; nmax
(KBr): 3354 (–OH), 3334 (–NH), 1234 (P]O), 1101 (P–O–Et); dH
(250 MHz, CDCl3): 0.97 (3H, t, JHH 7.0 Hz, –OCH2Me), 1.06 (3H, t, JHH
7.0 Hz, –OCH2Me), 3.42 (3H, s, PhOMe), 3.44–3.87 (4H, m,
–OCH2CH3), 4.44 (1H, d, JHP 25.0 Hz, CHP), 5.12 (1H, br s, –NH), 5.91
(1H, s, –OH), 6.51–6.62 (6H, m, ArH), 7.05 (2H, d, J 8.8 Hz, ArH); dC
2.2.29. Compound 3ac
White solid, mp 125 ꢀC. Found: C, 59.32; H, 6.90. C18H25N2O4P
requires: C, 59.33; H, 6.92%. Rf (AcOEt/hexane 20:80) 0.29; nmax