Paper
NJC
2 (a) S. Onuma, H. Kumamoto, M. Kawato and H. Tanaka,
Tetrahedron, 2002, 58, 2497; (b) K. Haraguchi, Y. Itoh,
H. Tanaka, M. Akita and T. Miyasaka, Tetrahedron, 1993,
49, 1371.
6.93 (t, 1H, J = 7.2 Hz), 6.24 (t, 1H, J = 7.2 Hz), 5.08 (s, 2H),
4.23 (s, 1H), 3.78 (d, 1H, J = 2.4 Hz), 3.72 (s, 3H), 3.51 (d, 2H,
J = 2.0 Hz), 3.43 (s, 2H), 2.18–2.11 (m, 2H). NMR 13C (101 MHz,
DMSO-d6) d = 162.3, 156.9, 150.5, 138.7, 131.2, 128.8, 122.1,
119.8, 111.2, 111.1, 87.2, 84.0, 70.4, 61.2, 55.3. MS (ESI): m/z =
357.15 [M + Na+], 333.1 [M ꢁ H]ꢁ.
3 (a) C. Len and G. Mackenzie, Tetrahedron, 2006, 62, 9085;
(b) D. F. Ewing, N. Fahmi, C. Len, G. Mackenzie, G. Ronco,
P. Villa and G. Shaw, Nucleosides Nucleotides, 1999, 18, 2613;
(c) D. F. Ewing, N. Fahmi, C. Len, G. Mackenzie and
A. Pranzo, J. Chem. Soc., Perkin Trans. 1, 2000, 3561;
(d) E. Lipka-Belloli, C. Len, G. Mackenzie, G. Ronco,
J. P. Bonte and C. Vaccher, J. Chromatogr., A, 2001,
943, 91; (e) D. F. Ewing, C. Len, G. Mackenzie, G. Ronco
and P. Villa, Tetrahedron: Asymmetry, 2000, 11, 4995;
( f ) A. Selouane, C. Vaccher, P. Villa, D. Postel and C. Len,
Tetrahedron: Asymmetry, 2002, 13, 407.
5-(2-Acetylphenyl)-20-deoxyuridine (15). White solid, mp 4
250 1C. NMR 1H (400 MHz, DMSO-d6) d = 11.26 (s, 1H), 8.49
(d, 1H, J = 5.2 Hz), 8.09 (s, 1H), 7.62–7.55 (m, 2H), 7.12 (t, 1H,
J = 6.8 Hz), 4.21 (d, 1H, J = 6.8 Hz), 3.78 (d, 1H, J = 2.4 Hz), 3.72
(s, 3H), 3.51 (d, 2H, J = 2 Hz), 3.43 (s, 2H), 2.08–1.99 (m, 2H),
1.65 (s, 3H). NMR 13C (101 MHz, DMSO-d6) d = 168.3, 165.5,
156.6, 152, 142.5, 139.9, 101.8, 87.2, 86.7, 84.4, 84.1, 74.1, 70.3,
70.2, 61.3, 61.2. MS (ESI): 369.34 [M + Na+], 345.35 [M ꢁ H]ꢁ.
5-(Thiophen-2-yl)-20-deoxyuridine (16). White foam (very
1
4 (a) T. Pesnot and G. K. Wagner, Org. Biomol. Chem., 2008,
6, 2884; (b) M. Segal and B. Fischer, Org. Biomol. Chem.,
2012, 10, 1571; (c) P. Naus, R. Pohl, I. Votruba, P. Dzubak,
M. Hajduch, R. Ameral, G. Birkus, T. Wang, A. S. Ray,
R. Mackman, T. Cihlar and M. Hocek, J. Med. Chem.,
2010, 53, 460; (d) M. Fukuda, M. Nakamura, T. Takada
and K. Yamana, Tetrahedron Lett., 2010, 51, 1732;
(e) M. F. Jacobsen, E. E. Ferapontova and K. V. Gothelf,
Org. Biomol. Chem., 2009, 7, 905; ( f ) C. Wanninger-Weiß
and H.-A. Wagenknecht, Eur. J. Org. Chem., 2008, 64;
(g) T. Ehrenschwender and H.-A. Wagenknecht, Synthesis,
2008, 3657; (h) M. L. Capobianco, A. Cazzato, S. Alesi and
G. Barbarella, Bioconjugate Chem., 2008, 19, 171; (i) A. Okamoto,
K. Tainaki, T. Unzai and I. Saito, Tetrahedron, 2007, 63, 3465;
( j) A. Okamoto, T. Inasaki and I. Saito, Tetrahedron Lett., 2005,
46, 791; (k) N. J. Greco and Y. Tor, J. Am. Chem. Soc., 2005,
127, 10784; (l) R. Hubert, T. Fiebig and H.-A. Wagenknecht,
Chem. Commun., 2003, 1878; (m) N. Amann and H.-A.
Wagenknecht, Synlett, 2002, 687; (n) N. Amann, E. Pandurski,
T. Fiebig and H.-A. Wagenknecht, Chem.–Eur. J., 2002, 8, 4877;
(o) N. Amann, E. Pandurski, T. Fiebig and H.-A. Wagenknecht,
Angew. Chem., Int. Ed., 2002, 41, 2978.
5 (a) V. Aucagne, S. Berteina-Raboin, P. Guenot and
L. A. Agrofoglio, J. Comb. Chem., 2004, 6, 717; (b) S. El Kazzouli,
S. Berteina-Raboin and L. A. Agrofoglio, Nucleosides, Nucleotides
Nucleic Acids, 2007, 26, 1395; (c) J. M. Sadler, O. Ojewoye and
K. L. Seley-Radtke, Nucleic Acids Symp. Ser., 2008, 52, 571;
(d) S. G. Srivatsan and T. Tor, J. Am. Chem. Soc., 2007,
129, 2044; (e) C. Peyron, R. Benhida, C. Bories and P. M.
Loiseau, Bioorg. Chem., 2005, 33, 439; ( f ) F. R. Wu¨st and
T. Kniess, J. Labelled Compd. Radiopharm., 2004, 47, 457; (g) A.
Haouz, V. Vannheusden, H. Munier-Lehman, M. Froeyen,
P. Herdewijn, S. Van Calenberg and M. Delarue, J. Biol. Chem.,
2003, 278, 4963; (h) T. L. Netzel, M. Zhao, K. Nafisi, J. Headrick,
M. S. Sigman and B. E. Eaton, J. Am. Chem. Soc., 1995, 117, 9119;
(i) A. J. Gutierrez, T. J. Terhost, M. D. Matteucci and B. C.
Froehler, J. Am. Chem. Soc., 1994, 116, 5540; ( j) P. Wigerinck,
L. Kerremans, P. Claes, R. Snoeck, P. Maugdal, E. De Clercq and
P. Herdewijn, J. Med. Chem., 1993, 36, 538; (k) M. E. Hassan,
Collect. Czech. Chem. Commun., 1991, 56, 1944; (l) G. T. Crips
and B. L. Flynn, Tetrahedron Lett., 1990, 31, 1347.
hygroscopic). NMR H (400 MHz, DMSO-d6) d = 11.66 (s, 1H),
8.18 (d, 1H, J = 4.8 Hz), 6.11 (t, 1H, J = 6.4 Hz), 5.21 (s, 1H), 5.10
(s, 1H), 4.21 (br s, 1H), 3.75 (d, 1H, J = 2.4 Hz), 3.56 (qd, 2H,
J = 10 Hz, J = 2.4 Hz), 2.06–2.04 (m, 2H). NMR 13C (101 MHz,
DMSO-d6) d = 165.6, 163.0, 154.3, 150.2, 142.8, 140.0, 101.2,
86.5, 84.0, 72.2, 69.7, 60.6 (1 signal hidden in solvent peaks).
MS (ESI): 333.35 [M + Na+], 309.35 [M ꢁ H]ꢁ.
5-(Furan-2-yl)-20-deoxyuridine (17). White foam (very hygro-
1
scopic). NMR H (400 MHz, DMSO-d6) d = 11.61 (s, 1H), 8.27
(s, 1H), 7.60 (s, 1H), 6.86 (d, 1H, J = 2.8 Hz), 6.51 (dd, 1H, J = 3.2 Hz),
6.23 (t, 1H, J = 6.4 Hz), 5.30–5.09 (m, 2H), 4.28–4.20 (m, 2H),
2.17–2.14 (m, 2H). MS (ESI): 317.25 [M + Na+], 293.25 [M ꢁ H]ꢁ.
5-(trans-b-Styryl)-20-deoxyuridine (18). White solid, mp =
145 1C. NMR 1H (400 MHz, DMSO-d6) d = 11.50 (s, 1H), 8.23
(s, 1H), 7.46 (d, 2H, J = 7.2 Hz), 7.41 (d, 1H, J = 16.2 Hz), 7.35
(t, 2H, J = 7.2 Hz), 7.23 (t, 1H, J = 10.8 Hz), 6.89 (d, 1H, J =
16.2 Hz), 6.19 (t, 1H, J = 6.4 Hz), 5.28 (s, 1H), 5.21 (s, 1H), 4.29
(s, 1H), 3.68 (d, 1H, J = 12.8 Hz), 3.62 (d, 1H, J = 10.8 Hz),
2.23–2.12 (m, 2H). NMR 13C (101 MHz, DMSO-d6) d = 162.20,
149.49, 138.08, 137.48, 128.69, 127.55, 127.27, 125.96, 121.22,
110.74, 87.42, 84.38, 69.95, 60.97 (one signal hidden in solvent
peaks). MS (ESI): 353.35 [M + Na+], 329.35 [M ꢁ H]ꢁ.
5-Phenyluracile (19). Beige solid (35 mg, 66%) mp 4 260 1C.
1
NMR H (400 MHz, DMSO-d6) d = 11.25 (s, 1H), 11.14 (s, 1H),
7.61 (s, 1H), 7.53 (d, 2H, J = 7.2 Hz), 7.35 (t, 2H, J = 7.2 Hz),
7.29 (1H, t, J = 7.2 Hz). NMR 13C (101 MHz, DMSO-d6) d = 163.1,
150.9, 139.7, 133.3, 128.0, 127.9, 126.9, 112.07. MS (ESI): 211.05
[M + Na+], 187.05 [M ꢁ H]ꢁ.
Acknowledgements
GS thanks Dr G. Santini and ESCOM for their financial support.
This work was supported in part by regional program of Region
Picardie, France.
Notes and references
1 (a) T. Cihlar and A. S. Ray, Antiviral Res., 2010, 85, 39;
(b) E. De Clercq, Antiviral Res., 2010, 85, 19; (c) E. De Clercq,
Curr. Opin. Pharmacol., 2010, 10, 507.
c
1994 New J. Chem., 2013, 37, 1989--1995
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2013