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• Monbaliu J.-C., Tinant B., and Marchand-Brynaert J. J. Mol. Struct. (2007) 10.1016/j.molstruc.2007.08.018
• Robiette R., Defacqz N., Peeters D., and Marchand-Brynaert J. Curr. Org. Synth. 2 (2005) 453-477
• Robiette R., Cheboub-Benchaba K., Peeters D., and Marchand-Brynaert J. J. Org. Chem. 68 (2003) 9809-9812 and references cited therein
• Kukhar V.P., and Hudson H.R. Aminophosphonic and Aminophosphinic Acids, Chemistry and Biological Activity (2000), J. Wiley & Sons Ltd, New York
• Moonen K., Laureyn I., and Stevens C.V. Chem. Rev. 104 (2004) 6177-6215
• Streith J., and Defoin A. Synthesis (1994) 1107-1117
• Vogt P.F., and Miller M.J. Tetrahedron 54 (1998) 1317-1348
• Yamamoto Y., and Yamamoto H. Eur. J. Org. Chem. (2006) 2031-2043
• Comins D.L., Kuethe J.T., Miller T.M., Fevrier F.C., and Brooks C.A. J. Org. Chem. 70 (2005) 5221-5234
• Kaname M., Yoshinaga K., Arakawa Y., and Yoshifuji S. Tetrahedron Lett. 40 (1999) 7993-7994
• Wróblewski A.E., and Glowacka I. Tetrahedron 61 (2005) 11930-11938
• Pudovik A.N., and Konovalova I.V. J. Gen. Chem. USSR 31 (1961) 1580
• Pudovik A.N., Konovalova I.V., and Ishmaevan E.A. Zh. Obshch. Khim. 33 (1963) 2509
• Claibourne E., Griffin C.E., and Daniewski W.M. J. Org. Chem. 35 (1970) 1691-1693
• Darling S.D., and Subramanian N. J. Org. Chem. 40 (1975) 2851-2852
• Lidström P., Tierney J., Wathey B., and Westman J. Tetrahedron 57 (2001) 9225
• Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284
• Perreux L., and Loupy A. Tetrahedron 57 (2001) 9199-9223
• Procedure for 1,2-(di-t-butyloxycarbonyl)-3-diethoxyphosphono-3,6-dihydro-1,2-pyridazine 3: A mixture of t-butyl azodicarboxylate (5.3 mmol) and 1 (5.3 mmol) with a few drops of toluene was stirred in a microwave oven under 650 W irradiation at 120 °C for 1 h. The reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel to give 3 as a yellow oil (>99%). Rf (ethyl acetate) = 0.6; 1H NMR (500 MHz; 50 °C, CDCl3) δ: 5.94 (br s, 2H), 5.04 (br d, 1H, J = 19.6 Hz), 4.41 (dd, 1H, J = 7 and 7.7 Hz), 4.27-4.15 (m, 4H), 3.76-3.63 (m, 1H), 1.47 (br s, 18H), 1.31 (t, 3H, J = 7.2 Hz), 1.25 (t, 3H, J = 7.2 Hz); 13C NMR (125 MHz; CDCl3, major rotamer) δ: 154.17, 152.68, 126.07, (d, JC-P = 7.7 Hz) 121.25, 81.02, 63.58 (d, JC-P = 6.5 Hz), 62.77 (d, JC-P = 6.1 Hz), 51.3 (d, JC-P = 162.3 Hz), 41.55 (d, JC-P = 2.1 Hz), 28.58 (m), 16.71 (m); 31P NMR (121 MHz; CDCl3, H3PO4) δ: 21.23; IR (NaCl, ν, cm-1) 2984, 2934, 1734, 1420, 1284, 1015, 952; ESI HRMS m/z for C18H33N2O7PNa [M+Na+]: calcd 443.1918; found 443.1921.
• Procedure for diethyl 1,2,3,6-tetrahydropyridazin-3-yl-3-phosphonate 4: To a solution of 3 (0.34 mmol) in chloroform (2.5 cm3) at room temperature was added TFA (2.72 mmol). After 15 h, the reaction mixture was concentrated in vacuo affording 4 as a yellow oil (95%). Rf [ethyl acetate/iPrOH 95:5] = 0.25; 1H NMR (300 MHz; CDCl3) δ: 6.06 (br s, 2H), 4.21 (m, 5H), 3.91-3.81 (m, 2H), 1.35 (t, 6H, J = 6.3 Hz); 13C NMR (75 MHz; CDCl3) δ: 122.81 (d, JC-P = 9.5 Hz), 121.19, 65.44 (d, JC-P = 155.4 Hz); 42.79, 16.56; 31P NMR (121 MHz; CDCl3, H3PO4) δ: 19.99; IR (NaCl, ν, cm-1) 3325, 1280, 1023; ESI HRMS m/z for C8H17N2O3PNa [M+Na+]: calcd 243.0875; found 243.0878.
• 2-Nitrosotoluene 5 was purchased from commercial source (Aldrich) as a dimeric form (colourless). In dichloroethane solution, the dissociation towards monomeric form was instantaneous (deep green solution). See:. Lee J., Chen L., West A.H., and Richter-Addo G.B. Chem. Rev. 102 (2002) 1019-1065
• Procedure for diethyl 3,6-dihydro-2-o-tolyl-1,2-oxazin-6-yl-6-phosphonate 6: A solution of 1 (6.58 mmol) in dichloroethane (10 cm3) and 2-nitrosotoluene (6.58 mmol) was stirred in a microwave oven under 500 W irradiation at 100 °C for 1 h. The reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel to give 6 as a brown oil (>99%). Rf (ethyl acetate) = 0.6; 1H NMR (500 MHz; CDCl3) δ: 7.16 (m, 4H), 6.13 (m, 2H), 5.1 (ddd, 1H, J = 7.6, 5.3 and 3 Hz), 4.14 (m, 4H), 3.88 (m, 1H), 3.57 (tdd, 1H, J = 7, 4.1 and 1.9 Hz), 2.33 (s, 3H), 1.28 (m, 6H); 13C NMR (125 MHz; CDCl3) δ: 147.76, 133.1, 130.99, 126.47, 126.34 (d, JC-P = 10 Hz), 125.85, 122.87 (d, JC-P = 5 Hz), 118.57, 75.68 (d, JC-P = 160 Hz), 63.49 (d, JC-P = 6.2 Hz), 62.86 (d, JC-P = 6.2 Hz), 52.15 (d, JC-P = 2.8 Hz), 18.33, 16.61 (dd, JC-P = 5.7 Hz); 31P NMR (121 MHz; CDCl3, H3PO4) δ: 18.2; IR (NaCl, ν, cm-1) 2935, 1495, 1454, 1209, 1068; ESI HRMS m/z for C15H22NO4PNa, [M+Na+]: calcd 334.1184; found 334.1171.
• Leach A.G., and Houk K.N. J. Org. Chem. 66 (2001) 5192-5200
• Tang M., and Pyne S.G. J. Org. Chem. 68 (2003) 7818-7824
• Procedure for diethyl syn-4,5-dihydroxy-2-o-tolyl-3,4,5,6-tetrahydro-1,2-oxazin-6-yl-6-phosphonate 7: A solution of 6 (9.4 mmol) in acetone (30 cm3) was treated successively by water (20 cm3), NMO (20.68 mmol) and K2OsO2(OH)4 (0.47 mmol) at room temperature. After 24 h, toluene (30 cm3) was added and concentrated in vacuo. The resulting dark oil was directly purified by column chromatography on silica gel to give 7 as a slightly yellow oil (>95%). Rf (ethyl acetate/iPrOH 95:5) = 0.43; 1H NMR (500 MHz; CD3CN) δ: 7.54 (m, 4H), 4.55 (dd, 1H, J = 10.3 and 9.6 Hz), 4.12 (m, 5H), 3.97 (ddd, 1H, J = 12.9, 8.4 and 4.4 Hz), 3.86 (large s, 1H), 3.55 (large s, 1H), 3.4 (dd, 2H, J = 7.1 and 2.8 Hz), 2.36 (s, 3H), 1.30 (t, 3H, J = 6.9 Hz), 1.26 (t, 3H, J = 7.1 Hz); 13C NMR (125 MHz; CD3CN) δ: 148.28, 134.28, 131.54, 127.17, 126.8, 119.22, 76.41 (d, JC-P = 158.1 Hz), 67.76 (d, JC-P = 13.8 Hz), 66.9 (d, JC-P = 11.3 Hz), 63.81 (d, JC-P = 6.7 Hz), 63.44 (d, JC-P = 6.3 Hz), 58.54, 18.04, 16.65 (d, JC-P = 5.8 Hz); 31P NMR (121 MHz; CDCN, H3PO4) δ: 20.37; IR (NaCl, ν, cm-1) 3389, 2982, 1489, 1230, 1047, 976; ESI HRMS m/z for C15H24NO6PNa [M+Na+]: calcd 368.1239; found 368.1245.
• This structure has been deposited at the Cambridge Crystallographic Data Centre with the number 666038.
• Procedure for diethyl 4-(o-tolylamino)-1,2,3-trihydroxybutylphosphonate 9: A solution of 7 (1.6 mmol) in ethanol (25 cm3) was stirred for 15 h at room temperature under H2 atmosphere in the presence of Pd-C as catalyst (5 mol %). Afterwards, the reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel to give 7 as a white solid (>99%). Rf (ethyl acetate/iPrOH 95:5) = 0.6; mp 105-106 °C; 1H NMR (500 MHz; CDCl3) δ: 7.04 (m, 2H), 6.65 (m, 2H), 4.39 (br s, 3H), 4.14 (m, 6H), 3.96 (m, 1H), 3.47 (dd, 1H J = 12.6 and 4.2 Hz), 3.22 (dd, 1H, J = 12.6 and 6.5 Hz), 2.12 (s, 3H), 1.28 (dt, 6H, J = 7.1 and 3.9 Hz); 13C NMR (125 MHz; CDCl3) δ: 146.23, 130.33, 127.29, 123.49, 118.17, 111.23, 73.77, 71.19, 71.12, 69.54 (d, JC-P = 158.3 Hz), 63.70 (d, JC-P = 6.9 Hz), 63.31 (d, JC-P = 6.9 Hz), 46.56, 17.73, 16.62 (t, JC-P = 6.1 Hz); 31P NMR (121 MHz; CDCl3, H3PO4) δ: 24.62; IR (NaCl, ν, cm-1) 3366, 1608, 1514, 1213, 1028; ESI HRMS m/z for C15H27NO6P [M+H+]: calcd 348.1576; found 348.1577.
• Dixon J.D., Ley S.V., and Reynolds D.J. Chem. Eur. J. 8 (2002) 1621-1636
• Lepore S.D., Schacht A., and Wiley M.R. Tetrahedron Lett. 43 (2002) 8777-8779
• Procedure for (Z)-diethyl 4-(o-tolylamino)-1-hydroxybut-2-enyl-phosphonate 10: To a solution of 6 (6.4 mmol) in a AcOH/water 1:2 mixture (90 cm3) was added zinc dust (10.2 mmol). The reaction mixture was heated at 70 °C for 12 h with vigorous stirring. The mixture was cooled down (20 °C) and solid K2CO3 was added portionwise to pH 7, and then 3 N aqueous KOH to pH 9. The mixture was then extracted with ethyl acetate (3 × 50 cm3). The organic phase was dried over MgSO4 and concentrated in vacuo, affording 10 as a brown solid (>99%). Rf (ethyl acetate) = 0.32; mp 72-73 °C; 1H NMR (500 MHz; CDCl3): 7.15-7.07 (m, 2H), 6.73-6.64 (m, 2H), 5.89 (td, 1H, J = 10.1 and 6.1 Hz), 5.73 (m, 1H), 4.83 (t, 1H, J = 10 and 7.5 Hz), 4.23-4.19 (m, 4H), 3.94-3.85 (m, 2H), 2.18 (s, 3H), 1.36 (t, 6H, J = 7.1 Hz); 13C NMR (125 MHz; CDCl3) δ: 145.97, 132.32 (d, JC-P = 12.6 Hz), 130.52, 127.53 (d, JC-P = 3.8 Hz), 123.20, 118.14, 110.75, 66.13 (d, JC-P = 160.9 Hz), 63.52 (t, JC-P = 7.9 Hz), 41.12, 17.89, 16.86 (d, JC-P = 5.5 Hz); 31P NMR (121 MHz; CDCl3, H3PO4) δ: 23.05; IR (NaCl, ν, cm-1) 3323, 1605, 1514, 1238, 1051; ESI HRMS m/z for C15H24NO4PNa [M+Na+]: calcd 336.1341; found 336.1342.
• Dodda R., and Zhao C.-G. Org. Lett. 8 (2006) 4911-4914
• Blazeswka K., Paneth P., and Gajda T. J. Org. Chem. 72 (2007) 878-887
• Shishido Y., and Kibayashi C. J. Org. Chem. 57 (1992) 2876-2883
• Procedure for diethyl 2,5-dihydro-1-o-tolyl-1-pyrrol-2-yl-2-phosphonate 12: To a solution of 10 (0.91 mmol), imidazole (0.91 mmol), triethylamine (0.91 mmol) and freshly recrystallized CBr4 (0.91 mmol) in dry dichloromethane (5 cm3) was added portionwise PPh3 (0.91 mmol) at 20 °C for 10 min. After 15 h, the reaction mixture was concentrated in vacuo, diluted with AcOEt, washed with 10% aqueous NH4Cl (1×), brine (1×) and water (2×). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The oily residue was purified by column chromatography on silica gel to give 12 as a yellow oil (75%). Rf (dichloromethane/ethyl acetate 3:1) = 0.33; 1H NMR (500 MHz; CDCl3): δ 7.09 (ddd, 2H, J = 12, 9.9 and 4.7 Hz), 6.91 (dt, 2H, J = 7.2 and 1.9 Hz), 5.99 (tq, 1H, J = 6.1 and 3.1 Hz), 5.99-5.95 (m, 1H), 5.02 (dq, 1H, J = 5.9, 5.8 and 2.3 Hz), 4.58-4.41 (m, 1H), 3.92 (m, 4H), 3.70 (tddd, 1H, J = 19.5, 14.1, 3.7, and 2 Hz), 2.33 (s, 3H), 1.13 (dt, 6H, J = 7.1 and 5.5 Hz); 13C NMR (125 MHz; CDCl3) δ: 149.02 (d, JC-P = 2.7 Hz), 133.52, 131.40, 129.87 (d, JC-P = 11.3 Hz), 126.70, 124.46 (d, JC-P = 5.6 Hz), 123.33, 120.71, 66.18 (d, JC-P = 168.3 Hz), 62.65 (d, JC-P = 7.1 Hz), 62.65 (d, JC-P = 7.3 Hz), 61.87, 19.54, 16.50 (dd, JC-P = 11.7 and 5.7 Hz); 31P NMR (121 MHz; CDCl3, H3PO4) δ: 21.98; IR (NaCl, ν, cm-1) 3446, 2249, 1493, 1240, 1055, 1026; ESI MS m/z (%) for C15H23NO3P [M+H+]: 296.12 (10), 279.27 (100).
• Robiette R., Marchand-Brynaert J., and Peeters D. J. Mol. Struct. (THEOCHEM) 587 (2002) 159-169
• Kaname M., Mashige H., and Yoshifyji S. Chem. Pharm. Bull. 49 (2001) 531-536
• Rao H., Jin Y., Fu H., Jiang Y., and Zhao Y. Chem. Eur. J. 12 (2006) 3636-3646