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1
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2642566088
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Minotti, G.; Menna, P.; Salvatorelli, E.; Cairo, G.; Gianni, L. Pharmacol. Rev., 2004, 56, 185-229.
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(2004)
Pharmacol. Rev
, vol.56
, pp. 185-229
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Minotti, G.1
Menna, P.2
Salvatorelli, E.3
Cairo, G.4
Gianni, L.5
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3
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0001853919
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Vanelle, P.; Terme, T.; Giraud, L.; Crozet, M. P. Recent Res. Devel. Org. Chem., 2000, 4, 1-28.
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(2000)
Recent Res. Devel. Org. Chem
, vol.4
, pp. 1-28
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Vanelle, P.1
Terme, T.2
Giraud, L.3
Crozet, M.P.4
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4
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0002632751
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Vanelle, P.; Terme, T.; Gellis, A., Crozet, M. P. Recent Adv. Devel. Ory. Chem., 2000, 1, 27-41.
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(2000)
Recent Adv. Devel. Ory. Chem
, vol.1
, pp. 27-41
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Vanelle, P.1
Terme, T.2
Gellis, A.3
Crozet, M.P.4
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6
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33646877668
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Vanelle, P, Ed, Research Signpost, Trivandrum
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Terme, T.; Crozet, M. P.; Maldonado, J.; Vanelle, P. In Electron Transfer Reactions in Organic Synthesis, Vanelle, P., Ed.; Research Signpost, Trivandrum, 2002, pp 1-42.
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(2002)
Electron Transfer Reactions in Organic Synthesis
, pp. 1-42
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Terme, T.1
Crozet, M.P.2
Maldonado, J.3
Vanelle, P.4
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7
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0034641454
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Vanelle, P.; Terme, T.; Crozet M. P. Tetrahedon Lett., 2000, 41, 6383-6385.
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(2000)
Tetrahedon Lett
, vol.41
, pp. 6383-6385
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Vanelle, P.1
Terme, T.2
Crozet, M.P.3
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8
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0019480945
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Kerdesky, F. A. J.; Ardecky, R. J.; Lakshmikantham, M. V.; Cava, M. P. J. Am. Chem. Soc., 1981, 103, 1992-1996.
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(1981)
J. Am. Chem. Soc
, vol.103
, pp. 1992-1996
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Kerdesky, F.A.J.1
Ardecky, R.J.2
Lakshmikantham, M.V.3
Cava, M.P.4
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9
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38949159635
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4 (246.26): C, 68.28; H, 5.73. Found: C, 68.21; H, 5.78.
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4 (246.26): C, 68.28; H, 5.73. Found: C, 68.21; H, 5.78.
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10
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38949092843
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New derivatives: 4, orange solid, mp 125°C (methyl alcohol, 1H NMR (CDCl3) δ 2.10 (s, 6H, 2xCH3, 2.29 (s, 6H, 2xCH3, 3.81 (s, 6H, 2xOCH3, 13C NMR (CDCl3) δ 13.0 (2xCH3, 13.3 (2xCH3, 61.4 (2xOCH3, 123.5 (2xC, 140.4 (2xC, 142.9 (2xC, 154.3 (2xC, 184.9 (2xC=O, Anal. Calcd for C16H18O4 (274.31, C, 70.06; H, 6.61. Found: C, 70.47; H, 6.74. 5, yellow solid, mp 203°C (methyl alcohol, 1H NMR (CDCl3) δ 4.01 (s, 6H, 2xOCH3, 4.49 (s, 4H, 2xCH2Br, 4.76 (s, 4H, 2xCH2Br, 13C NMR (CDCl3) δ20.4 (2xCH2Br, 21.5 (2xCH2Br, 63.1 (2xOCH3) 123.5 (2xC, 140.8 (2xC, 142.8 (2xC, 155.3 (2xC, 181.0 (2xC=O, Anal. Calcd for C16H14Br4O4 589-90, C, 32.58; H, 2.39. Found
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4 (412.09): C, 46.63; H, 3.42. Found. C, 46.18; H, 3.43.
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11
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0017263002
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Paull, K. D.; Zee-Cheng, R. K. Y.; Cheng, C. C. J. Med. Chem., 1976, 19, 337-339.
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(1976)
J. Med. Chem
, vol.19
, pp. 337-339
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Paull, K.D.1
Zee-Cheng, R.K.Y.2
Cheng, C.C.3
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12
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38949194166
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New products: 7, yellow solid, mp 297°C (CCl4, 1H NMR (CDCl3) δ 2.01 (s, 6H, 2xCH3, 2.29 (s, 6H, 2xCH3, 7.57 (m, 6H, 8.09 (m, 4H, 13C NMR (CDCl3) δ12.9 (2xCH3, 13.6 (2xCH3, 122.4 (2xC, 128.7 (4xCH, 129.5 (2xC, 130.5 (4xCH, 133.7 (2XCH, 139.1 (2xC, 143.1 (2xC, 164.5 (2xC, 165.0 (2xC=O, 183.3 (2xC=O, Anal. Calcd for C28H22O6 (454.47, C, 74.00; H, 4.88. Found: C, 73.78; H, 4.89. 8, yellow solid, mp 233°C (ethyl alcohol, 1H NMR (CDCl3) δ 4.27-4.86 (m, 8H, 4xCH2Br, 7.61 (m, 6H, 8.29 (m, 4H, 13C NMR (CDCl3) δ 19.8 (2xCH2Br, 20.8 (2xCH2Br, 124.5 (2xC, 128.6 (2xC, 128.9 (4xCH, 130.6 (4xCH, 134.3 (2xCH, 139.0 (2xC, 143.5 (2xC, 146.5 (2xC, 164.2 (2xC=0, 179.9 2xC=0, Anal. Calcd for C28H18Br4O
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+; characteristic tetrachloride isotop peaks are observed.
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13
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38949168065
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General procedure for tetrakis-SRN1 reaction of 6 with nitroalkanes: Under nitrogen atmosphere, a solution of tetra-butylammonium hydroxide (40% in water, 2.9 mL, 3.84 mmol) was treated with nitroalkane (3.84 mmol) for 1 h. A solution of 2,3,6,7-tetrakis(chloromethyl)-5,8-dimethoxynaphthalene-1,4-dione 6(0.20 g, 0.48 mmol) in dichloromethane (20 mL) was added and the mixture was irradiated with a fluorescent lamps (2 × 60 W) for 10 min. at room temperature under an inert atmosphere. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3 × 10 mL, The combined organic layers were washed twice with water 30 mL, dried over MgSO4 and removed under reduced pressure. Purification by chromatography on silica gel eluting with chloroform and recrystallization from methanol led to the corresponding product 10a-h
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4 and removed under reduced pressure. Purification by chromatography on silica gel eluting with chloroform and recrystallization from methanol led to the corresponding product 10a-h.
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14
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38949196336
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New derivatives: 10a, orange solid, mp 207°C, 1H NMR (CDCl3) δ 1.54 (s, 12H, 4xCH3, 1.62 (s, 12H, 4xCH3, 3.28 (s, 4H, 2xCH2, 3.34 (s, 4H, 2xCH2, 3.74 (s, 6H, 2xOCH3, 13C NMR (CDCl3) δ26.1 (4xCH3, 26.7 (4xCH3, 36.4 (2xCH2, 37.0 (2xCH2, 62.0 (2xOCH3, 87.8 (2xCNO2, 88.5 (2xCNO2, 124.0 (2xC, 139.6 (2xC, 144.6 (2xC, 155.7 (2xC, 182.9 (2xC=O, Anal. Calcd for C28H38N4O12 (622.62, C, 54.01; H, 6.15; N, 9.00. Found: C, 54.09; H, 6,29; N, 9.05. 10b, orange so-lid, mp 132°C, 1H NMR.(CDCl3) δ 1.58-1.69 (m, 16H, 8xCH2, 1.79-1.90 (m, 8H, 4xCH2, 2.49-2.60 (m, 8H, 4xCH2, 3.32 (s, 4H, 2xCH2, 3.43 (s, 4H, 2xCH2, 3.75 s, 6H, 2xOCH3, 13C NMR
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12 (838.98): C, 62.99; H, 7.45; N, 6.68. Found: C, 62.43; H, 7.53; N, 6.70.
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15
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38949083115
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General procedure for reaction of 6 with substituted sulfinate sodium salt. A solution of substituted sulfinate sodium salt (5.76 mmol) in dimethylsulfoxide (10 mL) was added dropwise to a solution of tetrachloride 6 (0.20 g, 0.48 mmol) in dimethylsulfoxide (6 mL) and stirred under inert atmosphere for 10 mm. The reaction mixture was poured into cold water and the precipitate was formed. After filtration, the crude product was recrystallized from methanol gave the corresponding tetrakis-S-alkylated product.
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General procedure for reaction of 6 with substituted sulfinate sodium salt. A solution of substituted sulfinate sodium salt (5.76 mmol) in dimethylsulfoxide (10 mL) was added dropwise to a solution of tetrachloride 6 (0.20 g, 0.48 mmol) in dimethylsulfoxide (6 mL) and stirred under inert atmosphere for 10 mm. The reaction mixture was poured into cold water and the precipitate was formed. After filtration, the crude product was recrystallized from methanol gave the corresponding tetrakis-S-alkylated product.
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16
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0000196929
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Liu, L. K.; Chi, Y.; Jen, K.-Y. J. Org. Chem., 1980, 45, 406-410.
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(1980)
Org. Chem
, vol.45
, pp. 406-410
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Liu, L.K.1
Chi, Y.2
Jen, K.-Y.J.3
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17
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38949197766
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New derivatives: 10e, orange solid mp 266°C, 1H NMR (CDCl3) δ 3.62, s, 6H, 2xOCH3, 4.93 (a, 4H, 2xCH2SO2, 5.05 (a, 4H, 2xCH2SO2, 7.59-7.71 (m, 12H, 7.84 (m, 4H, 7.98 (m, 4H, 13C NMR (CDCl3) δ53.4 (2xCH2SO2, 54.2 (2xCH2SO2, 63.6 (2xOCH3, 125.0 (2xC, 128.0 (4xCH, 128.3 (4xCH, 129.5 (4xCH, 129.6 (4xCH, 132.8 (2XC, 134.4 (4xCH, 138.8 (4xC, 139.3 (2xC, 156.6 (2xC, 180.4 (2xC=O, Anal. Calcd for C40H34O12S4 (834.95, C, 57.54; H, 4.10. Found: C, 57.18; K 4.00. 10f, orange solid, mp 254°C, 1H NMR (CDCl3) δ 2.45 (s, 12M, 4xCH3, 3.63 (s, 6H, 2xOCH3, 4.89 (s, 4H, 2xCH2SO2, 5.01 (s, 4H, 2xCH2SO2, 7.39 (d, J, 8.2 Hz, 8H, 7.79 d, J, 8.2 Hz, 8H
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4 (754.99); C, 50.91; H, 6.68. Found: C, 50.99; H, 6.57.
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