318 Maghsoodlou et al.
J = 25.1 Hz, CHP), 6.53 (2H, d, J = 7.7 Hz), 6.74 (1H,
t, J = 7.4 Hz), 7.11 (2H, t, J = 7.3 Hz), 7.67 (2H, dd,
J = 2.2, J = 8.8 Hz), 8.19 (2H, d, J = 8.2 Hz).
Compound 11: Colorless crystals, mp 97–98◦C.
IR (KBr) νmax (cm−1): 3305 (NH); 1H NMR (300 MHz;
CDCl3) δ: 1.09, 1.32 (6H, 2t, J = 7.10 Hz, 2CH3), 3.77,
3.91 (6H, 2s, 2OCH3), 3.61–3.72 (1H, m), 3.86–3.90
(1H, m), 4.14–4.23 (2H, m), 4.61 (1H, br, NH), 5.29
(1H, d, J = 24.2 Hz, CHP), 6.45 (2H, d, J = 6.8 Hz),
6.61–6.70 (3H, m), 7.11 (2H, t, J = 7.7), 7.38 (1H, dd,
J = 2.5, 8.7 Hz); 13C NMR (75 MHz; CDCl3) δ: 16.21
(d, J = 5.9 Hz, CH3), 16.45 (d, J = 5.9 Hz, CH3), 47.50
(d, J = 155.2 Hz), 55.31 (s, OCH3), 55.72 (s, OCH3),
63.00 (d, J = 6.9 Hz, OCH2), 63.10 (d, J = 6.9 Hz,
OCH2), 98.39 (d, J = 2.3 Hz) 104.77, 113.61, 116.69,
118.09, 128.91 (d, J = 4.3 Hz), 129.08, 146.28 (d,
J = 14.8 Hz), 158.22 (d, J = 13.5 Hz), 160.45 (d,
J = 2.8 Hz); 31P NMR (121 MHz; CDCl3) δ: 23.92.
Anal. Calcd for C19H26NO5P: C, 60.15; H, 6.91; N,
3.69. Found: C, 60.32; H, 7.14; N, 3.59.
Compound 6: Colorless crystals, mp 57–59◦C. IR
1
(KBr) νmax (cm−1): 3305 (NH); H NMR (300 MHz;
CDCl3) δ: 1.18, 1.30 (6H, 2t, J = 7.1 Hz), 3.75–3.84
(1H, m), 3.96–4.22 (3H, m), 4.60 (1H, br, NH), 4.74
(1H, d, J = 24.4 Hz, CHP), 6.56 (2H, d, J = 8.4 Hz),
6.73 (1H, t, J = 7.3 Hz), 7.12 (2H, t, J = 7.4 Hz), 7.31
(2H, d, J = 8.5 Hz), 7.42 (2H, dd, J = 2.3, 8.6 Hz).
Compound 7: Colorless crystal, mp 63–65◦C. IR
1
(KBr) νmax (cm−1): 3325 (NH); H NMR (400 MHz;
CDCl3) δ: 1.13, 1.28 (6H, 2t, J = 7.0 Hz, 2CH3), 2.31
(3H, s, CH3), 3.64–3.73 (1H, m, OCH2), 3.89–3.99
(1H, m, OCH2), 4.05–4.16 (2H, m, 2OCH2), 4.73 (1H,
d, J = 24.1 Hz, CHP), 5.10 (1H, br, NH), 6.57–6.70
(3H, m), 7.07–7.14 (4H, m), 7.34 (2H, dd, J = 2.2,
8.2 Hz).
Compound 8: Colorless crystals, mp 134–136◦C.
IR (KBr) νmax (cm−1): 3305 (NH); 1H NMR (300 MHz;
CDCl3) δ: 3.44, 3.86 (6H, 2d, J = 10.8 Hz, 2OCH3),
4.62 (1H, br, NH), 5.42 (1H, d, J = 24.8, CHP), 6.58
(2H, d, J = 8.6 Hz), 6.71 (1H, t, J = 7.4 Hz), 7.09–
7.15 (2H, m), 7.21–7.28 (2H, m), 7.39–7.42 (1H, m),
7.57–7.61 (1H, m).
REFERENCES
[1] Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood,
J. M. J Med Chem 1989, 32, 1652.
[2] Peyman, A.; Stahl, W.; Wagner, K.; Ruppert, D.; Budt,
K.-H. Bioorg Med Chem Lett 1994, 4, 2601.
[3] Atherton, F. R.; Hassal, C. H.; Lambert, R. W. J Med
Chem 1986, 29, 29.
[4] Maier, L.; Spoerri, H. Phosphorus, Sulfur, Silicon Re-
lat Elem 1991, 61, 69.
[5] Emsley, J.; Hall, D. In: The Chemistry of Phospho-
rous; Harper & Row: London, 1976; p. 494.
[6] Meyer, J. H.; Barlett, P. A. J Am Chem Soc 1998, 120,
4600.
[7] Miller, D. J.; Hammond, S. M.; Anderluzzi, D.;
Bugg, T. D. H. J Chem Soc, Perkin Trans 1998, 1,
131.
[8] Manabe, K.; Kobayashi, S. Chem Commun 2000, 669.
[9] Xu, F.; Luo, Y.; Deng, M.; Shen, Q. Eur J Org Chem
2003, 4728.
[10] Ranu, B. C.; Hajra, A.; Jana, J. Org Lett 1999, 1, 1141.
[11] Chandrasekhar, S.; Jaya Prakash, S.; Jagadeshwar,
V.; Narsihmula, Ch. Tetrahedron Lett 2001, 42, 5561.
[12] Kudrimoti, S.; Bommena, Rao V. Tetrahedron Lett
2005, 46, 1209.
[13] Heydari, A.; Zarei, M.; Alijanianzadeh, R.; Tavakol,
H. Tetrahedron Lett 2001, 42, 3629.
[14] Yadav, J. S.; Reddy, B. V. S.; Madan, C. Synlett 2001,
1131.
[15] Yadav, J. S.; Reddy, B. V. S.; Raj, S.; Reddy, K. B.;
Prasad, A. R.; Synthesis 2001, 2277.
[16] Kaboudin, B.; Nazari, R. Tetrahedron Lett 2001, 42,
8211.
[17] Bhattacharya, A. K.; Rana, K. C. Tetrahedron Lett
2008, 49, 2598.
[18] Heydari, A.; Hamedi, H.; Pourayoubi, M. Catal Com-
mun. 2007, 8, 1224.
[19] Vahdat, S. M.; Baharfar, R.; Tajbakhsh, M.; Heydari,
A.; Baghbanian, S. M.; Khaksar, S. Tetrahedron Lett
2008, 49, 6501.
[20] Hosseini-Sarvari, M. Tetrahedron 2008, 64,
5459.
[21] Zolfigol, M. A. Tetrahedron 2001, 57, 9509.
Compound 9: Colorless crystals, mp 109–111◦C.
IR (KBr) νmax (cm−1): 3310 (NH); 1H NMR (300 MHz;
CDCl3) δ: 3.52, 3.86 (6H, 2d, J = 10.6 Hz, 2OCH3),
4.65 (1H, br, NH), 5.35 (1H, d, J = 24.7, CHP), 6.57
(2H, d, J = 8.7 Hz), 6.73 (1H, t, J = 8.6), 7.13 (2H,
t, J = 8.6), 7.21–7.26 (1H, dd, J = 1.8, 8.4 Hz), 7.43
(1H, s), 7.51–7.55 (1H, dd, J = 2.5, 8.4 Hz); 13C NMR
(75 MHz; CDCl3) δ: 51.19 (d, 1 J = 153.1 Hz, CHP),
2
2
53.86 (d, J = 6.9 Hz, OCH3), 53.96 (d, J = 6.9 Hz,
OCH3), 113.58, 118.70, 127.46 (d, J = 3.0 Hz),
128.93 (d, J = 4.2 Hz), 129.25, 129.30, 129.57 (d,
3 J = 2.3 Hz), 133.70, 133.98 (d, 3 J = 7.27 Hz), 145.47
(d, 2 J = 14.6 Hz); 31P NMR (121 MHz; CDCl3) δ:
24.06. Anal. Calcd for C15H16Cl2NO3P: C, 50.02; H,
4.48; N, 3.89. Found: C, 50.23; H, 4.56; N, 3.66.
Compound 10: Colorless crystals, mp 76–78◦C.
IR (KBr) νmax (cm−1): 3310 (NH); 1H NMR (300 MHz;
CDCl3) δ: 1.15, 1.33 (6H, 2t, J = 6.8 Hz, 2CH3), 3.90–
4.11 (2H, m), 4.19–4.29 (2H, m), 4.61 (1H, br, NH),
5.53 (1H, d, J = 26.9 Hz, CHP), 6.68–6.75 (3H, m),
6.92–6.98 (1H, m), 7.11–7.18 (4H, m); 13C NMR
(75 MHz; CDCl3) δ: 16.15 (d, 3 J = 6.5 Hz, OCH3),
3
1
16.45 (d, J = 6.5 Hz, CH3), 53.20 (d, J = 152.2 Hz,
CHP), 63.14 (d, 2 J = 7.5 Hz, OCH2), 63.64 (d,
2 J = 7.5 Hz, OCH2), 113.69 (CH), 115.59 (CH), 118.87
(CH), 122.54 (CH), 125.43 (CH), 129.30 (CH), 129.60
(d, J = 2.6 Hz), 129.73 (d, J = 2.7 Hz), 136, 145.95 (d,
J = 14.48 Hz); 31P NMR (121 MHz; CDCl3) δ: 20.92.
Anal. Calcd for C17H20ClFNO3P: C, 54.92; H, 5.42; N,
3.77. Found: C, 55.09; H, 5.56; N, 3.65.
Heteroatom Chemistry DOI 10.1002/hc