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, E)-ethyl 3-(5-bromo-2-hydroxyphenyl)acrylate (1e)
, , pp.515877-70
, the expected product 1e (271 mg) was obtained in pure form as a yellowish solid from 5-bromo-2hydroxybenzaldehyde (250 mg, 1.24 mmol, 1 eq). Yield: 81%.-R f = 0.40 (PE / EtOAc 70:30).-IR (neat): 3350, 2985, 1685, 1625 cm-1 .-1 H NMR (300 MHz, Acetone-d 6 ) ? (ppm) = 9, p.1
, E)-ethyl 3-(2-hydroxy-5-nitrophenyl)acrylate (1f)
, , pp.153136-77
, According to the general procedure B for Wittig reaction (page 198), the expected product 1f (146 mg) was obtained in pure form as a yellowish solid from 2-hydroxy-5-nitrobenzaldehyde
, Acetone-d 6 ) ? (ppm) = 10.54 (bs, 1H, OH), vol.8, p.0, 1615.
, trifluoromethyl)benzylidene)pentane-2,4-dione 7h (5 mg, 0.017 mmol, 1 eq) by the Lumos Lamp in CH 3 CN. Yield: 23%.-R f = 0.17 (cyclohexane / EtOAc 80:20).-IR
, 7.78 (m, 1H, H 7
, 81 (s, 3H, H 8 ), 2.71 (s, 3H, H 8' ), vol.2, p.75
, , pp.125-131
, , p.270
, HRMS (DCIMS) m/z calcd
, , pp.121-124
, the expected product 8i was obtained in pure form as a yellow solid from the irradiation of 3-(2Azido-4-dimethylamino-phenyl)-acrylic acid ethyl ester 7i (5 mg, 0.019 mmol, 1 eq) by the Lumos Lamp in CH 3 CN. Yield: 27%.-R f = 0.49 (cyclohexane / EtOAc 70:30).-1 H NMR (300 MHz
,
, DCIMS m/z (%) 233 [M+H] + (100).-m p, pp.131-134
, 3-Diacetyl-6-dimethylamino-1H-indole (8j)
, the expected product 8j was obtained in pure form as an orange solid from the irradiation of 3-(2azido-4-(dimethylamino)benzylidene)pentane-2,4-dione 7j (5 mg, 0.018 mmol, 1 eq) by the Lumos Lamp in CH 3 CN. Yield: 33%.-R f = 0.4 (cyclohexane / EtOAc 70:30), p.300
, CDCl 3 ) ? (ppm) = 9
,
, According to the general procedure H for photochemistry of azidocinnamates (page 201), the expected product 8k was obtained in pure form as a yellow solid from the irradiation of 2-(2Azido-4,5-dimethoxy-benzylidene)-malonic acid diethyl ester 7k (5 mg, 0.013 mmol, 1 eq) by the Lumos Lamp in CH 3 CN. Yield: 63%.-R f = 0.24 (cyclohexane / EtOAc 70:30), Dimethoxy-1H-indole-2,3-dicarboxylic acid diethyl ester (8k), p.300
, 45 (s, 1H, H 4 ), 6.83 (s, 1H, CDCl 3 ) ? (ppm) = 9.49 (bs, 1H, NH), vol.7
, CDCl 3 ) ? (ppm) = 164.5, 160.9, pp.125-128
, Ethyl 2-methylquinoline-3-carboxylate (9a)
,
, the expected product 9a was obtained in pure form as a yellow oil from the irradiation of 2-(2Azido-benzylidene)-3-oxo-butyric acid ethyl ester 7d (30 mg, 0.116 mmol, 1 eq) by the Tungsten Lamp in H 2 O / EtOH (1:1). Yield
, 00 (s, 3H, H 11 ), vol.3
, Azido-benzylidene)-malonic acid diethyl ester 7f (30 mg, 0.131 mmol, 1 eq) by the Tungsten
, , pp.7-59
, According to the general procedure H for photochemistry of azidocinnamates (page 201), the expected product 9c was obtained in pure form as a brown solid from the irradiation of 2-(2Azido-benzylidene)-malonic acid diethyl ester 7e (30 mg, 0.103 mmol, 1 eq) by the Tungsten
, Acetone-d 6 ) ? (ppm) = 11.39 (bs, 1H, NH), 8.44 (s, 1H, H 4 ), 7.80 (dd, 1H, 4 J 8-6 = 1.4 Hz, vol.1, pp.171-174, 1640.
, Methyl-7-(trifluoromethyl)quinolin-3-yl)ethanone (9d)
, According to the general procedure H for photochemistry of azidocinnamates (page 201), the expected product 9d was obtained in pure form as a yellow solid from the irradiation of 3-(2azido-4-(trifluoromethyl)benzylidene)pentane-2,4-dione 7h (30 mg, 0.101 mmol, 1 eq) by the Tungsten
, azido-4-(dimethylamino)benzylidene)pentane-2,4-dione 7j (30 mg, 0.110 mmol, 1 eq) by the Tungsten
, 23 (cyclohexane / EtOAc 70:30).-IR (neat): 2925, 1666, 1616, 1511, 1422 cm-1 .-1 H NMR (300 MHz
, 35 (s, 1H, H 4 ), 8.66 (d, 3 J 6-5 = 9, vol.8
, 65 (s, 3H, H 10 ).-13 C NMR (75 MHz, vol.2, p.1347
, , pp.118-121
, Hydroxy-4-(prop-2-yn-1-yloxy)benzaldehyde (10)
, , pp.67268-67302
, According to the general procedure A for O-alkylation, vol.10, p.47
, g, 14.5 mmol, 1 eq). Yield: 58%.-R f = 0.67 (PE / EtOAc 80:20).-IR (neat): 3459, 3241, 1639, 1224, 1124 cm-1 .-1 H NMR (300 MHz, CDCl 3 ) ? (ppm) = 11.4 (s, 1H, OH), vol.2, p.4
, hydroxy-4-(prop-2-yn-1-yloxy)phenyl)acrylate (Cinn1) According to the general procedure B for Wittig reaction, p.3
, Yield: 88%.-R f = 0.15 (PE / EtOAc 80:20).-IR (neat) 3330, 2125, 1685 cm-1 .-1 H NMR (300 MHz, Acetone-d 6 ) ? (ppm) = 9, Cinn1 (330 mg) was obtained in pure form as a white solid from 10 (400 mg, 2.27 mmol, 1 eq)
, Acetone-d 6 ) ? (ppm) = 168.4, EtOAc (3 x 30 mL), dried over Na 2 SO 4 , filtered and evaporated. Purification by column chromatography eluting with (PE / EtOAc 95:5) furnished the desired aldehyde 12a as an orange solid (85 mg), 3.13 (t, 1H, 4 J 3'-1' = 2.4 Hz, H 3' ), 1.27 (t, 3H, 3 J 11-10 = 7.1 Hz, H 11 ).-13 C NMR (75 MHz, pp.32-35
, 2-nitrophenyl)acrylate (12b) According to the general procedure B for Wittig reaction (page 198), the expected product 12b (112 mg) was obtained in pure form as a yellow solid from 12a (225 mg, 0.64 mmol, 1 eq). Yield: 80%, p.300
, CDCl 3 ) ? (ppm) = 8.02 (d, 1H, 3 J 7-8 = 15.6 Hz
,
, , p.236
, HRMS (DClMS) m/z calcd
, , pp.41-44
, Ethyl (E)-3-(4-hydroxy-2-nitrophenyl)acrylate (12c)
, A mixture of 12b (400 mg, 1.42 mmol, 1 eq) and para-toluenesulfonic acid (49 mg, p.28
, After complete conversion, monitored by TLC, the solvent was removed under reduced pressure. Purification of the crud material by column chromatography on silica gel with PE / EtOAc (90:10), afford 12c as yellow powder (304 mg). Yield: 90%.-R f = 0.28 (PE / EtOAc 80:20).-IR (neat): 3297, 2925, 1685, 1195 cm-1 .-1 H NMR (300 MHz, eq) in anhydrous EtOH (25 mL) was heated at 80°C overnight
, Acetone, pp.1616-1617, 1722.
, Methyl-7-(prop-2-yn-1-yloxy)-2H-chromen-2-one (Cou2)
, , pp.67268-53
, Evaporation of the solvent gave a pale yellow solid purified by chromatography on silica gel (PE / EtOAc 80:20) to obtain the desired compound as a white solid (37 mg). Yield: 89%.-R f = 0.43 (CH 2 Cl 2 ).-IR (neat, CH 3 CN (20 mL) was irradiated overnight with the tungsten lamp, p.1605, 1681.
, , vol.6
, , pp.6093-71
, 0 g, 22 mmol, 1 eq) and diethyl malonate (4.2 g, 26 mmol, 1.1 eq) in anhydrous EtOH (30 mL) was added piperidine, vol.2, p.370
, The resulting precipitate was collected and washed with cold EtOH to afford after crystallization the expected coumarine 13 as a yellow solid (2.9 g). Yield: 58%.-R f = 0.4 (PE / EtOAc 60:40).-IR (neat): 3538, 1726, 1677 cm-1 .-1 H NMR (300 MHz, Acetone-d 6 ) ? (ppm) = 8.58 (s, 1H, After refluxing for 20 h, the reaction mixture was cooled in an ice bath and a precipitate was then formed
, , pp.67268-51
, the expected product Cou3 (383 mg) was obtained in pure form as a yellow solid from 13 (500 mg, 2.10 mmol, 1 eq)
,
, Acetone-d 6 ) ? (ppm), p.273
, Prop-2-yn-1-yloxy)quinolin-2(1H)-one (Qui1)
, the expected product Qui1 (147 mg) was obtained in pure form as a white solid from 7-hydroxy-1H-quinolin-2-one (300 mg, 1.86 mmol, 1 eq)
,
, , vol.6, p.31
, Acetone-d 6 ) ? (ppm), HRMS (DCIMS) m/z calcd, pp.249-252
, 75 mmol, 1 eq) was added rapidly to a solution of sodium azide, p.37
, CDCl 3 ) ? (ppm) = 3.78 (dd, 2H, 3 J = 10.1 Hz, 3 J = 5.3 Hz, 1,4,7-Tris-(tert-butoxycarbonylmethyl)-10-(prop-2-ynyl)-1,4,7,10-tetraazacyclododecane (16) To a solution of DO3A-tBu (595 mg, 1 mmol, 1 eq) in dried CH 3 CN (12 mL) was added K 2 CO 3 (414 mg, 3 mmol, 3 eq), then propargyl bromide (295 mg, 2 mmol, 2 eq) dropwise. The reaction mixture was heated at 45°C and stirred for 72 h. The solvent was then evaporated and the pale brown residue was, pp.2102-2103, 2948.
, neat): 2975, 1670, 1218 cm-1 .-1 H NMR (300 MHz, MeOD) ? (ppm) = 3.48 (s, 2H, p.75
, , p.497
, According to the general procedure I for the cleavage of t-Butyl esters (page 201), the expected product 16a (443 mg) was obtained as a white hygroscopic solid from 16 (200 mg, 0.36 mmol, 1 eq). Yield: quant.-IR (neat, p.3350, 1256.
, ESIMS m/z (%), p.461
, 10-(prop-2-ynyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate (La2) According to the general procedure J for Ln 3+ complexation
, Yield: 66%.-IR (neat): 3430, 2974, 2860, 1629 cm-1 .-1 H NMR (300 MHz, D 2 O) ? (ppm) = 3.95-3.03 (m, 25H), signal of 1.2 eq triethylammonium salt at 1.28 ppm (t, 11H, La2 (124 mg) was obtained as a white solid from 16a (139 mg, 0.36 mmol, 1 eq), vol.3, p.20
, HRMS (ESIMS) m/z calcd for C 17 H, p.622
, prop-2-ynyl)-1,4,7,10-tetraazacyclododecane-1,4,7triyl)triacetate (Eu2) According to the general procedure J for Ln 3+ complexation
, ESIMS m/z (%) 533 (83), 535 [M+H] + (100).-HRMS (ESIMS) m/z calcd for C, vol.17, p.26, 2494.
, Azidoethoxy)-2-hydroxybenzaldehyde (17)
, m g, 1.81 mmol, 1 eq) and 1-azido-2-bromoethane 14b (336 mg, 2.26 mmol, 1.5 eq). Yield: 27%.-R f = 0.67 (CH 2 Cl 2 ).-IR (neat): 3421, 2116, 1631, 1190 cm-1 .-1 H NMR (300 MHz, CDCl 3 ) ? (ppm) = 11, the expected product 17 (105 mg) was obtained in pure form as a white solid from, vol.2, p.4
, HRMS (DCIMS) m/z calcd for C 9, pp.58-61
, azidoethoxy)-2-hydroxyphenyl)acrylate (Cinn1'), p.3
, the expected product Cinn1' (134 mg) was obtained in pure form as a white solid from 17 (223 mg, 0.64 mmol, 1 eq), pp.3-7
, = 16.0 Hz, H 7 ), 7.56 (d, 1H, 3 J 6-5 = 9.6 Hz, H 6 ), 6.55 (m, 2H, H 5+3 ), vol.6
, 66 (t, 2H, 3 J 2'-1' = 5.1 Hz, H 2' ), vol.3, p.75
, , p.188
, La1-Cinn1 According to the general procedure K for CuAAC reaction
, mg) was obtained in pure form as a yellow hygroscopic solid from La1 (30 mg, 0.054 mmol, 1 eq) and Cinn1 (14.73 mg, 0.06 mmol, 1.1 eq). Yield: 44%.-R f = 0.32 (CH 3 CN / H 2 O 70:30).t R = 3.38 min
, 14 (t, 3H, 3 J 11-10 = 6.9 Hz, H 11 ).-ESIMS m/z (%) 798 [M+H] + (100).-HRMS (ESIMS) m/z calcd for C 30 H 41 LaN 7 O 10 798.1978, found 798.1993 [M+H] + .UV absorption in Tris buffer ? max = 327 nm (? = 7600 M-1 .cm-1 ).-Fluorescence ? em = 394, vol.1
, Eu1-Cinn1 According to the general procedure K for CuAAC reaction
, 25 mg) was obtained in pure form as a yellow hygroscopic solid from Eu1 (30 mg, 0.053 mmol, 1 eq) and Cinn1 (14.4 mg, 0.058 mmol, 1.1 eq)
, HRMS (ESIMS) m/z calcd for C, vol.30, p.41
, EuN, vol.7, issue.10
, , p.1065
, HRMS (ESIMS) m/z calcd for C 42 H 54 LaN 8 O 16 1065.2721, found 1065, p.2748
, UV absorption in Tris buffer ? max = 336 nm (? = 4400 M-1 .cm-1 )
, Eu1-Cinn3 According to the general procedure K for CuAAC reaction
, mg) was obtained in pure form as a yellow hygroscopic solid from Eu1 (50 mg, 0.088 mmol, 1 eq) and Cinn3 (50 mg
, (m, 22H).-ESIMS m/z (%) 752 [M+H] + (100).-HRMS (ESIMS) m/z calcd for C 28 H 35 LaN 7 O 9 752.1560, found 752.1576 [M+H] + .UV absorption in Tris buffer ? max = 322 nm (? = 7100 M-1 .cm-1 ) .-Fluorescence ? em = 394 nm (Tris
, Eu1-Cou1 According to the general procedure K for CuAAC reaction
, 21 mg) was obtained in pure form as a yellow hygroscopic solid from Eu1 (30 mg, 0.053 mmol, 1 eq) and Cou1 (11.7 mg, 0.058 mmol, 1.1 eq). Yield: 51%.-R f = 0.17 (CH 3 CN / H 2 O 70:30).-t R = 2.88 min.-IR (neat, p.766, 1395.
, HRMS (ESIMS) m/z calcd for C, vol.28, p.35
, cm-1 ).-Fluorescence ? em = 392 nm (Tris, ? ex = 321 nm, ? F = 17%).-Time-resolved luminescence ? em = 590, 616, 698 nm (Tris, ? ex = 321 nm
, La1-Cou2 According to the general procedure K for CuAAC reaction
, 5 mg) was obtained in pure form as a yellow hygroscopic solid from La1 (30 mg, 0.054 mmol, 1 eq) and Cou2 (13 mg, 0.06 mmol, 1.1 eq). Yield: 55%.-R f = 0.22 (CH 3 CN / H 2 O 70:30).-t R = 3.17 min, p.1163, 1384.
, DMSO-d 6 ) ? (ppm) = 8.33 (s, 1H
,
, HRMS (ESIMS) m/z calcd for C 29 H 37 LaN 7 O 9 766.1716, found 766.1723 [M+H] + .-UV absorption in Tris buffer ? max = 320 nm (? = 6200 M-1 .cm-1 ) .-Fluorescence ? em = 394 nm (Tris, ? ex = 322 nm, ? F = 39%)
, the expected product Yield: 33%.-R f = 0.22 (CH 3 CN / H 2 O 70:30).-t R = 3.15 min, p.3405, 1396.
, 1867 [M+H] + .-UV absorption in Tris buffer ? max = 319 nm (? = 5850 M-1 .cm-1 ).-Fluorescence ? em = 398 nm (Tris, ? ex = 320 nm, ? F = 33%).-Time-resolved luminescence ? em = 591, HRMS (ESIMS) calcd for C 29 H 37 EuN 7 O 9 778.1851, found 778, vol.615
, La1-Cou3 According to the general procedure K for CuAAC reaction
, 30 mg, 0.054 mmol, 1 eq) and Cou3 (16.29 mg, 0.059 mmol, 1.1 eq). Yield, La1-Cou3 (20 mg) was obtained in pure form as a yellow hygroscopic solid from La1
, 08 (dd, 1H, 3 J 6-5 = 8.7 Hz, 4 J 6-8 = 2.2 Hz, H 6 ), 5.33 (s, 2H, vol.7
, HRMS (ESIMS) m/z calcd for C 31 H 39 LaN 7 O 11 824.1771, found 824.1789 [M+H] + .-UV absorption in Tris buffer ? max = 347 nm (? = 4950 M-1 .cm-1 ).-Fluorescence ? em = 406 nm (Tris, ? ex = 346 nm, ? F = 40%)
, Eu1-Cou3 According to the general procedure K for CuAAC reaction
, 14 mg) was obtained in pure form as a yellow hygroscopic solid from Eu1 ((30 mg, 0.051 mmol, 1 eq) and Cou3 (15.42 mg, 0.056 mmol, 1.1 eq)
, ESIMS m/z (%), p.836, 1608.
, Fluorescence ? em = 392 nm (Tris, ? ex = 327 nm, ? F = 3%)
, According to the general procedure K for CuAAC reaction
, 43 mg) was obtained in pure form as a yellow hygroscopic solid from Eu2 (45 mg, 0.084 mmol, 1 eq) and Cinn1' (23.3 mg, 0.084 mmol, 1 eq)
, HRMS (ESIMS) m/z calcd
, cm-1 ).-Fluorescence ? em = 392 nm (Tris, ? ex = 326 nm, ? F = 8.3%).-Time-resolved luminescence ? em = 590, UV absorption in Tris buffer ? max = 326 nm (Tris, ? = 12000 M-1, vol.616
, According to the general procedure K for CuAAC reaction
, mg) was obtained in pure form as a yellow hygroscopic solid from La2 (36 mg, 0.069 mmol, 1 eq) and Cou1' (16 mg, 0.069 mmol, 1 eq). Yield
, DMSO-d 6 + D 2 O) ? (ppm) = 8.26 (s, 1H, H 11 )
, 4.46 (bs, 2H, H 10 ), 3.70-1.93 (m, 24H
, nm (Tris, ? = 2450 M-1 .cm-1 ).-Fluorescence ? em = 394 nm (Tris, ? ex = 320 nm, ? F = 8.5%)
, According to the general procedure K for CuAAC reaction
, 037 mmol, 1 eq) and Cou1' (8.6 mg, 0.037 mmol, 1 eq). Yield: 27%.-R f = 0.20 (CH 3 CN / H 2 O 70:30).-t R = 2.68 min.-IR (neat): 3426, Eu2-Cou1' (7.5 mg) was obtained in pure form as a yellow hygroscopic solid from Eu2 (20 mg, 0, pp.1391-1392, 1605.
, 1695, found 764.1714 [M+H] + .-UV absorption in Tris buffer ? max = 321 nm (Tris, ? = 3950 M-1 .cm-1 ).-Fluorescence ? em = 392 nm (Tris, ? ex = 321 nm, ? F = 8.3%).-Time-resolved luminescence ? em = 590, HRMS (ESIMS) m/z calcd for C 28 H 35 LaN 7 O 9, vol.616
, La2-Cou1a According to the general procedure K for CuAAC reaction
, mg) was obtained in pure form as a yellow hygroscopic solid from La2 (45 mg, 0.086 mmol, 1 eq) and Cou1a (19.5 mg, 0.1 mmol, 1.2 eq). Yield
, DMSO-d 6 ) ? (ppm) = 9, IR (neat): 2984, 1734, 1590, 1085 cm-1 .-1 H NMR (300 MHz, vol.8
, UV absorption in Tris buffer ? max = 287, 316 nm (Tris, ? = 7000, 5500 M-1 .cm-1 ).-Fluorescence ? em = 398
, HRMS (ESIMS) m/z calcd for C 26 H 31 EuN 7 O 8 722.1433, found 722.1447 [M+H] + .UV absorption in Tris buffer ? max = 287 nm (Tris, ? = 9850 M-1 .cm-1 ).-Fluorescence ? em = 384 nm (Tris, ? ex = 287 nm, ? F = 0.2%).-Time-resolved luminescence ? em = 592, vol.616, pp.1398-1399, 1612.