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LETTER
dd, J = 7.3, 7.9 Hz), 7.56 (2 H, dd, J = 7.9, 7.3 Hz), 7.37 (2
H, d, J = 6.7 Hz). 13C NMR (125 MHz, CDCl3/TMS):
d = 185.3, 179.5, 148.7, 141.8, 141.2, 135.7, 133.4, 131.5,
131.1, 129.0, 128.7, 128.5, 128.1, 123.4. HRMS (EI): m/z
calcd for C16H10O4S [M+]: 298.0300; found: 298.0298.
(9) Analytical and Spectral Data of 7
References and Notes
(1) (a) Mayer, G.; Heckel, A. Angew. Chem. Int. Ed. 2006, 45,
4900. (b) Igarashi, T.; Shimokawa, M.; Iwasaki, M.; Nagata,
K.; Fujii, M.; Sakurai, T. Synlett 2007, 1436. (c) Bochet,
C. G. J. Chem. Soc., Perkin Trans. 1 2002, 125.
Yellow solid; mp 165.5–167.8 °C. IR (KBr): 3420, 2359 cm–1.
1H NMR (500 MHz, CDCl3/TMS): d = 8.20 (3 H, m), 7.92
(1 H, dd, J = 7.9 Hz), 7.81 (2 H, d, J = 8.5 Hz), 7.78 (1 H, dd,
J = 7.9 Hz), 7.50 (3 H, m), 7.32 (2 H, d, J = 8.5 Hz), 7.19 (2
H, d, J = 7.0 Hz), 5.30 (1 H, s), 2.42 (3 H, s). 13C NMR (125
MHz, CDCl3/TMS): d = 178.1, 145.0, 144.3, 143.4, 142.2,
142.1, 136.8, 135.0, 134.5, 133.0, 130.8, 129.9, 129.8,
128.6, 128.6, 128.3, 128.2, 123.4, 21.7. HRMS–FAB: m/z
calcd for C23H18N2O5S2 [M + H]+: 467.0735; found:
467.0742.
(2) (a) Fodor, S. P. A.; Read, J. L.; Pirrung, M. C.; Stryer, L.; Lu,
A. T.; Solas, D. Science 1991, 251, 767. (b) Mcgall, G. H.;
Barone, A. D.; Diggelmann, M.; Fodor, S. P. A.; Gentalen,
E.; Ngo, N. J. Am. Chem. Soc. 1997, 119, 5081. (c) Mayer,
G.; Heckel, A. Angew. Chem. Int. Ed. 2006, 45, 4900.
(3) (a) Pillai, V. N. R. Org. Photochem. 1987, 9, 225.
(b) Givens, R. S.; Kueper, L. W. Chem. Rev. 1993, 93, 55.
(c) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000,
100, 2091. (d) Pelliccioli, A. P.; Wirz, J. Photochem.
Photobiol. Sci. 2002, 1, 441. (e) Mayer, G.; Heckel, A.
Angew. Chem. Int. Ed. 2006, 45, 4900. (f) Wang, P. F.; Hu,
H. Y.; Wang, Y. Org. Lett. 2007, 9, 1533.
(4) Givens, R. S.; Kueper, L. W. Chem. Rev. 1993, 93, 55.
(5) Kitani, S.; Sugawara, K.; Tsutsumi, K.; Morimoto, T.;
Kakiuchi, K. Chem. Commun. 2008, 2103.
(6) (a) Ito, K.; Maruyama, J. Chem. Pharm. Bull. 1983, 31,
3014. (b) Ito, K.; Maruyama, J. Chem. Pharm. Bull. 1987,
35, 1255.
(10) Analytical and Spectral Data of 1b
Yellow solid; mp 122.3–123.5 °C. IR (KBr): 3433, 2359 cm–1.
1H NMR (500 MHz, CDCl3/TMS): d = 8.26 (1 H, d, J = 7.9
Hz), 8.06 (1 H, d, J = 7.9 Hz), 7.85 (1 H, dd, J = 7.9 Hz),
7.79 (1 H, dd, J = 7.9 Hz), 7.48 (3 H, m), 7.27 (2 H, d, J = 7
Hz), 4.95 (1 H, s). 13C NMR (125 MHz, CDCl3/TMS):
d = 175.0, 139.6, 133.5, 133.5, 132.5, 129.8, 129.6, 129.1,
128.9, 128.8, 128.7, 127.4, 122.7, 47.5. HRMS–ESI: m/z
calcd for C32H20O6S2Na [2 M – 2 N2 + Na]+: 587.0599;
found: 587.0600.
(7) In this step, we observed an interesting side reaction and for
details, see: Zhang, Y.; Tanimoto, H.; Nishiyama, Y.;
Morimoto, T.; Kakiuchi, K. Heterocycles 2011, 83, 2337.
(8) Analytical and Spectral Data of 6
(11) Treatment of 8h with 2.5 equiv of 1b in the presence of a
catalytic amount of 10% HCl aq in CHCl3 at 60 °C afforded
diprotection product in 81% yield. The complete experi-
mental procedures and analytical data are shown in the
Supporting Information.
Yellow solid; mp 213.7–214.2 °C. IR (KBr): 1685, 1310 cm–1.
1H NMR (500 MHz, CDCl3/TMS): d = 9.54 (1 H, s), 8.24 (1
H, d, J = 6.7 Hz), 8.15 (1 H, d, J = 7.9 Hz), 7.97 (1 H, dd,
J = 7.9, 7.9 Hz), 7.83 (1 H, dd, J = 6.7, 7.9 Hz), 7.63 (1 H,
Synlett 2012, 23, 367–370
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