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-
92
-
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45749101600
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2-i-PrOH) to afford the pure adduct 3.
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2-i-PrOH) to afford the pure adduct 3.
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-
-
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93
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-
24744451593
-
-
a = 14.75 in DMSO) in the absence of any dehydrating agents is quite unique, and we are currently performing experiments to explore the general scope of this reaction. See also: Kumamoto, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2005, 2254.
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a = 14.75 in DMSO) in the absence of any dehydrating agents is quite unique, and we are currently performing experiments to explore the general scope of this reaction. See also: Kumamoto, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2005, 2254.
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-
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94
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45749153287
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All new compounds gave satisfactory analytical and spectral data
-
All new compounds gave satisfactory analytical and spectral data.
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-
-
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95
-
-
45749141564
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-
The higher reactivity of purine (1g) at the N9 position is well established. For example, see ref. 6. Compound 3q: mp 123-125°C (hexane-CH2Cl2, FT-IR (KBr, ν, 1698, 1595, 1576, 1496, 1413 cm-1. 1H NMR (400 MHz, CDCl3, δ, 1.85 (1 H, dddd, J, 14.0, 12.0, 5.4, 3.6 Hz, 2.16-2.23 (1 H, m, 2.32-2.39 (1 H, m, 2.48-2.62 (3 H, m, 2.95 (1 H, ddt, J, 14.1, 4.9, 1.7 Hz, 3.26 (1 H, dd, J, 14.1, 11.7 Hz, 4.89 (1 H, tt, J, 11.5, 4.2 Hz, 8.13 (1 H, s, 8.98 (1 H, s, 9.17 (1 H, s, 13C NMR (100 MHz, CDCl3, δ, 22.0, 30.7, 40.5, 46.9, 54.4, 134.6, 143.2, 149.1, 150.9, 152.4, 206.3. Compound 3r: mp 143-144°C (hexane-CH2Cl2, FT-IR (KBr, ν, 1708, 1606, 1559, 1488, 1412 cm-1. 1H NMR (400 MHz, CDCl3, δ, 1.83-1.96 (1 H, m, 2.17-2.26 (1 H, m, 2.37 1 H, ddt, J, 14.6, 1
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3): δ = 21.9, 31.3, 40.4, 47.6, 55.7, 124.4, 140.0, 145.5, 153.7, 161.0, 205.3.
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-
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96
-
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45749156305
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Compound 3d: mp 69-70°C (hexane-CH2Cl2, FT-IR (KBr, ν, 1685, 1596, 1521, 1448 cm-1. 1H NMR (400 MHz, CDCl3, δ, 3.60 (2 H, t, J, 6.4 Hz, 4.65 (2 H, t, J, 6.4 Hz, 7.47 (2 H, m, 7.59 (1 H, tt, J, 7.3, 1.2 Hz, 7.91-7.95 (3 H, m, 8.23 (1 H, s, 13C NMR (100 MHz, CDCl 3, δ, 37.9, 44.0, 128.0 (2x, 128.7 (2x, 133.7, 136.0, 144.0, 152.0, 196.5. Compound 3e: mp 87-89°C (hexane-CH 2Cl2, FT-IR (KBr, ν, 1687, 1538 cm-1. 1H NMR (400 MHz, CDCl3, δ, 3.50 (2 H, t, J, 6.1 Hz, 4.55 (2 H, t, J, 6.1 Hz, 7.50 (2 H, t, J, 7.8 Hz, 7.62 (1 H, m, 7.93 (2 H, m, 8.34 (2 H, s, 13C NMR (100 MHz, CDCl3, δ, 39.2, 39.7, 128.0 (2x, 128.9 (2x, 134.2, 135.6, 143.2 2x, 195.8
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3): δ = 39.2, 39.7, 128.0 (2x), 128.9 (2x), 134.2, 135.6, 143.2 (2x), 195.8.
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97
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0037037978
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For recent examples of imidazole-catalyzed Morita-Baylis-Hillman reactions, see: a
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For recent examples of imidazole-catalyzed Morita-Baylis-Hillman reactions, see: (a) Luo, S.; Zhang, B.; He, J.; Janczuk, A.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2002, 43, 7369.
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(2002)
Tetrahedron Lett
, vol.43
, pp. 7369
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Luo, S.1
Zhang, B.2
He, J.3
Janczuk, A.4
Wang, P.G.5
Cheng, J.-P.6
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99
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0346502285
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(c) Luo, S.; Wang, P. G.; Cheng, J. P. J. Org. Chem. 2004, 69, 555.
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(2004)
J. Org. Chem
, vol.69
, pp. 555
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Luo, S.1
Wang, P.G.2
Cheng, J.P.3
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100
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2942536316
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(d) Luo, S.; Mi, X.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2004, 45, 5171.
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(2004)
Tetrahedron Lett
, vol.45
, pp. 5171
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Luo, S.1
Mi, X.2
Wang, P.G.3
Cheng, J.-P.4
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101
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33846347896
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(e) Davies, H. J.; Ruda, A. M.; Tomkinson, N. C. O. Tetrahedron Lett. 2007, 48, 1461.
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(2007)
Tetrahedron Lett
, vol.48
, pp. 1461
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Davies, H.J.1
Ruda, A.M.2
Tomkinson, N.C.O.3
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103
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45749098103
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2O, 0.6 GPa, 60°C, 20 h), except for methyl acrylate (87% conversion yield).
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2O, 0.6 GPa, 60°C, 20 h), except for methyl acrylate (87% conversion yield).
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