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Organic & Biomolecular Chemistry
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2H), 4.34 (s, 2H). 13C NMR (100 MHz, CD3OD): δ 150.7, 148.1, 2-Benzyl-8-benzyl-6-(furyl-2)imidazo[1,2-a]pyrazin-3(7H)-one
139.7, 139.0, 137.9, 135.5, 132.5, 132.5, 129.1, 128.6, 128.4,
(
B9): dark yellow solid; yield 30%; DAOnI:a1l0y.1ti0c3a9l/C7ROPB0H15P5L4CB
128.2, 127.2, 126.9, 126.9, 121.9, 118.0, 112.7, 111.6, 38.2, (Phenomenex, C8, 250 x 4.6 mm column): 50% acetonitrile
28.8. ESI-HRMS: m/z [M+H]+ calcd for 417.1715, found with 0.1% trifluoroacetic acid, 1.0 mL/min at 370 nm, Rt: 4.586
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417.1717. Melting point: 179-181 oC.
min, 98%. H NMR (400 MHz, CD3OD): δ 8.50 (s, 1H), 7.69 (s,
1H), 7.43~7.27 (m, 10H), 7.08 (d, J = 4 Hz, 1H), 6.60 (s, 1H),
4.56 (s, 2H), 4.34 (s, 2H). 13C NMR (100 MHz, CD3OD): δ 149.2,
2-Benzyl-8-benzyl-6-(5-methylfuryl)imidazo[1,2-a]pyrazin-
3(7H)-one (B5): light brown solid; yield 30%; Analytical RP 148.2, 144.3, 138.0, 136.5, 135.4, 134.0, 128.6, 128.3, 128.1,
HPLC (Phenomenex, C8, 250
x
4.6 mm column): 55% 121.0, 111.9, 110.5, 107.6, 37.8, 29.0. ESI-HRMS: m/z [M+H]+
acetonitrile with 0.1% trifluoroacetic acid, 1.0 mL/min at 320 calcd for 382.1556, found 382.1545. Melting point: 184-186 oC.
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nm, Rt: 6.953 min, 99%. H NMR (400 MHz, CD3OD): δ 7.72 (s,
1H), 7.27~7.09 (m, 10H), 6.72 (d, J = 3.2 Hz, 1H), 6.07 (d, J = 2.8 2-Benzyl-8-benzyl-6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-
Hz, 1H), 4.31 (s, 2H), 4.07(s, 2H). 13C NMR (100 MHz, CD3OD): δ 3(7H)-one (B10): yellow solid; yield 52%; Analytical RP HPLC
154.7, 148.1, 147.3, 137.9, 136.6, 135.4, 133.9, 128.9, 128.5, (Phenomenex, C8, 250 x 4.6 mm column): 55% acetonitrile
128.3, 128.2, 126.9, 126.8, 121.9, 111.7, 108.2, 106.7, 37.7, with 0.1% trifluoroacetic acid, 1.0 mL/min at 370 nm, Rt: 7.431
29.1. ESI-HRMS: m/z [M+H]+ calcd for 396.1712, found min, 98%. 1H NMR (400 MHz, CD3OD): δ 7.91 (s, 1H), 7.68~7.66
396.1703. Melting point: 185-188 oC.
(d, J = 8 Hz, 2H), 7.40~7.38 (d, J = 8 Hz, 2H), 7.32~7.17 (m, 8H),
7.04~7.02 (d, J = 8 Hz, 2H), 4.46 (s, 2H), 4.21 (s, 2H), 3.83 (s,
3H). 13C NMR (100 MHz, CD3OD): δ 161.4, 139.6, 138.4, 136.8,
2-Benzyl-8-benzyl-6-(furyl-3)imidazo[1,2-a]pyrazin-3(7H)-one
(
B6): yellow solid; yield 43%; Analytical RP HPLC (Phenomenex, 135.6, 128.9, 128.5, 128.4, 128.2, 128.2, 126.9, 126.7, 125.8,
C8, 250 x 4.6 mm column): 50% acetonitrile with 0.1% 114.2, 109.3, 54.6, 37.4, 29.7. ESI-HRMS: m/z [M+H]+ calcd for
trifluoroacetic acid, 1.0 mL/min at 370 nm, Rt: 4.551 min, 98%. 422.1869, found 422.1863. Melting point: 184-187 oC.
1H NMR (400 MHz, CD3OD): δ 8.54 (s, 1H), 8.19 (s, 1H), 7.65 (s,
1H), 7.43 (d, J = 8 Hz, 2H), 7.37~7.23 (m, 8H), 7.02 (d, J = 4 Hz, 2-Benzyl-8-benzyl-6-(naphthyl)imidazo[1,2-a]pyrazin-3(7H)-
1H), 4.58 (s, 2H), 4.34 (s, 2H). 13C NMR (100 MHz, CD3OD): δ one (B11): dark yellow solid; yield 12%; Analytical RP HPLC
147.7, 144.5, 142.3, 136.7, 135.5, 128.9, 128.5, 128.3, 128.2, (Phenomenex, C8, 250 x 4.6 mm column): 63% acetonitrile
126.9, 126.7, 121.7, 109.1, 107.7, 37.4, 29.3. ESI-HRMS: m/z with 0.1% trifluoroacetic acid, 1.0 mL/min at 395 nm, Rt: 4.547
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[M+H]+ calcd for 382.1556, found 382.1557. Melting point: min, 96%. H NMR (400 MHz, CD3OD): δ8.76 (s, 1H), 8.52 (s,
191-194 oC.
1H), 8.00 (m, 4H), 7.56~7.11 (m, 14H), 4.62 (s, 2H), 4.34 (s, 2H).
13C NMR (100 MHz, CD3OD): δ150.01, 145.43, 144.34, 139. 60,
135.09, 133.67, 131.44, 129.69, 129.21, 129.05, 128.55, 128.41,
2-Benzyl-8-benzyl-6-(3-ethyoxycarbonylphenyl)imidazo[1,2-
a]pyrazin-3(7H)-one
(B7): dark yellow solid; yield 31%; 128.38, 128.32, 128.25, 128.17, 127.33, 126.96, 126.82, 126.55,
Analytical RP HPLC (Phenomenex, C8, 250 x 4.6 mm column): 126.35, 124.93, 124.66, 122.39, 120.53, 38.52, 22.11. ESI-
45% acetonitrile with 0.1% trifluoroacetic acid, 1.0 mL/min at HRMS: m/z [M+H]+ calcd for 442.1919, found 442.1915.
370 nm, Rt: 6.564 min, 98%. 1H NMR (400 MHz, CD3OD): δ 8.78 Melting point: 117-119 oC.
(s, 1H), 8.65 (s, 1H), 8.23 (d, J = 8 Hz, 1H), 8.07 (d, J = 8 Hz, 1H),
7.46 (d, J = 4 Hz, 2H), 7.39~7.24 (m, 9H), 4.61 (s, 2H), 4.42 (q, J 2-Benzyl-8-benzyl-6-(thienyl-2)imidazo[1,2-a]pyrazin-3(7H)-
= 8 Hz, 2H), 4.40~4.34 (m, 2H), 1.43 (t, J = 8 Hz, 3H). 13C NMR one (B12): yellow solid; yield 50%; Analytical RP HPLC
(100 MHz, CD3OD): δ 166.2, 150.4, 147.8, 140.1, 138.0, 136.6, (Phenomenex, C8, 250 x 4.6 mm column): 50% acetonitrile
135.5, 134.8, 130.8, 129.0, 128.6, 128.4, 128.2, 126.9, 126.8, with 0.1% trifluoroacetic acid, 1.0 mL/min at 380 nm, Rt: 8.969
110.6, 61.2, 37.9, 29.1, 13.3. ESI-HRMS: m/z [M+H]+ calcd for min, 96%. 1H NMR (400 MHz, DMSO): δ 8.71 (s, 1H), 7.86 (d, J
464.1974, found 464.1964. Melting point: 188-190 oC.
= 4 Hz, 1H), 7.64 (dd, J = 8 Hz, J = 4 Hz, 1H), 7.49~7.17 (m, 11H),
4.49 (s, 2H), 4.26 (s, 2H). 13C NMR (100 MHz, DMSO): δ 147.25,
139.20, 136.82, 136.49, 135.76, 128.77, 128.10, 128.03, 127.93,
127.76, 126.20, 126.12, 125.06, 124.60, 108.02, 37.17, 28.03.
2-Benzyl-8-benzyl-6-(benzofuranyl-2)imidazo[1,2-a]pyrazin-
3(7H)-one (B8): dark yellow solid; yield 58%; Analytical RP ESI-HRMS: m/z [M+H]+ calcd for 398.1327, found 398.1327.
HPLC (Phenomenex, C8, 250
x
4.6 mm column): 45% Melting point: 261-265 oC.
acetonitrile with 0.1% trifluoroacetic acid, 1.0 mL/min at 380
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nm, Rt: 6.564 min, 98%. H NMR (400 MHz, CD3OD): δ 8.55 (s, 2-Benzyl-8-benzyl-6-(phenyl)imidazo[1,2-a]pyrazin-3(7H)-one
1H), 7.57 (t, J = 6 Hz, 4H), 7.47 (d, J = 8 Hz, 3H), 7.31 (t, J = 8 Hz,
4H), 7.24 (m, 3H), 7.13 (s, 1H), 4.63 (s, 2H), 4.36 (s, 2H). 13C HPLC (Phenomenex, C8, 250
(
B13, DeepBlueCTM): light brown solid; yield 60%; Analytical RP
x
4.6 mm column): 50%
NMR (100 MHz, CD3OD): δ 155.0, 151.5, 149.1, 138.0, 137.7, acetonitrile with 0.1% trifluoroacetic acid, 1.0 mL/min at 380
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136.7, 132.8, 129.9, 129.1, 129.0, 128.9, 128.7, 128.4, 127.4, nm, Rt: 9.824 min, 97%. H NMR (400 MHz, CD3OD): δ 7.90 (s,
127.3, 127.1, 126.4, 124.1, 122.3, 120.5, 111.8, 110.3, 106.7, 1H), 7.55~7.17 (m, 15H), 4.37 (s, 2H), 4.11 (s, 2H). 13C NMR
100.0, 38.1, 29.2. ESI-HRMS: m/z [M+H]+ calcd for 432.1712, (100 MHz, CD3OD): δ 147.9, 139.6, 138.0, 137.8, 136.8, 136.7,
found 432.1703. Melting point: 207-209 oC.
134.5, 130.1, 129.8, 129.5, 129.1, 129.0, 128.9, 127.4, 127.2,
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