PAPER
Synthesis of Benzo[b]thiophenes and Naphthothiophenes
2099
IR (neat): 1622, 1586, 1500, 817, 805, 775 cm–1.
Klimkowski, V. J.; Kohn, T. J.; Lin, H.; McCowan, J. R.;
Palkowitz, A. D.; Smith, G. F.; Takeuchi, K.; Thrasher, K.
J.; Tinsley, J. M.; Utterback, B. G.; Yan, S. B.; Zhang, M.
J. Med. Chem. 1997, 40, 3489. (b) Takeuchi, K.; Kohn, T.
J.; Bastian, J. A.; Chirgadze, N. Y.; Denny, M. L.; Harper, R.
W.; Lin, H.; McCowan, J. R.; Gifford-Moore, D. S.; Richett,
M. E.; Sall, D. J.; Smith, G. F.; Zhang, M. Bioorg. Med.
Chem. Lett. 1999, 9, 759.
1H NMR (CDCl3): d = 3.02 (s, 3 H), 7.29 (dd, J = 8.5, 2.0 Hz, 1 H),
7.36–7.46 (m, 3 H), 7.55–7.58 (m, 2 H), 7.63–7.67 (m, 2 H), 7.71
(d, J = 8.8 Hz, 1 H), 7.74–7.77 (m, 1 H), 7.79 (d, J = 3.4 Hz, 1 H),
7.98 (dd, J = 8.1, 1.2 Hz, 1 H), 8.76 (d, J = 8.5 Hz, 1 H).
13C NMR (CDCl3): d = 18.0, 120.5, 123.3, 124.8, 125.1, 125.1,
125.7, 126.5, 126.5, 126.6, 127.1, 127.7, 128.7, 129.1, 130.6, 131.7,
132.0, 133.7, 134.0, 135.3, 140.4, 141.4.
(5) Norman, B. H.; Dantzig, A. H.; Kroin, J. S.; Law, K. L.;
Tabas, L. B.; Shepard, R. L.; Palkowitz, A. D.; Hauser, K.
L.; Winter, M. A.; Sluka, J. P.; Starling, J. J. Bioorg. Med.
Chem. Lett. 1999, 9, 3381.
(6) (a) Wright, C. D.; Stewart, S. F.; Kuipers, P. J.; Hoffman, M.
D.; Devall, L. J.; Kennedy, J. A.; Ferin, M. A.; Theuson, D.
O.; Conroy, M. C. J. Leukocyte Biol. 1994, 55, 443.
(b) Bleavins, M. R.; de La Igelsia, F. A.; McCay, J. A.;
White, L.; Kimber, L. Jr.; Munson, A. E. Toxicology 1995,
98, 111.
(7) (a) Benincori, T.; Gladiali, S.; Rizzo, S.; Sannicolò, F.
J. Org. Chem. 2001, 66, 5940. (b) Sannicolò, F.; Benincori,
T.; Rizzo, S.; Gladiali, S.; Pulacchini, S.; Zotti, G. Synthesis
2001, 2327.
HRMS (TOF-CI): m/z [M + H]+ calcd for C23H17S2: 357.0771;
found: 357.0775.
Anal. Calcd for C23H16S2: C, 77.49; H, 4.52. Found: C, 77.25; H,
4.48.
3-(2-Naphthylsulfanyl)-2,5-diphenylfuran (10)
White solid; mp 146–147 °C (hexane–EtOAc).
IR (neat): 3056, 1623, 1586, 1500, 1487, 1479, 799, 767, 688, 675
cm–1.
1H NMR (CDCl3): d = 6.75 (s, 1 H), 7.25–7.33 (m, 2 H), 7.39–7.46
(m, 7 H), 7.67–7.78 (m, 6 H), 8.10–8.12 (m, 2 H).
13C NMR (CDCl3): d = 111.5, 112.6, 123.9, 125.3, 125.6, 125.7,
126.0, 126.6, 127.1, 127.7, 128.0, 128.2, 128.5, 128.8, 128.8, 129.9,
130.0, 131.7, 133.8, 134.1, 134.2, 152.9.
HRMS (TOF-CI): m/z [M + H]+ calcd for C26H19OS: 379.1156;
found: 379.1155.
(8) Wilson, W. D.; Wang, Y.; Kusuma, S.; Chandrasekaran, S.;
Boykin, D. W. Biophys. Chem. 1986, 24, 101.
(9) Pal, S. K.; Bhattacharaya, S.; Batabyal, S. K.; Pradhan, T.
K.; Ganguly, T. J. Photochem. Photobiol., A 2007, 189, 86.
(10) (a) Ichikawa, J.; Wada, Y.; Okauchi, T.; Minami, T. Chem.
Commun. 1997, 1537. (b) Ichikawa, J.; Wada, Y.; Fujiwara,
M.; Sakoda, K. Synthesis 2002, 1917.
Anal. Calcd for C26H18OS: C, 82.51; H, 4.79. Found: C, 82.68; H,
4.50.
(11) (a) Mukherjee, C.; De, A. Synlett 2002, 325. (b)Mukherjee,
C.; Kamila, S.; De, A. Tetrahedron 2003, 59, 4767.
(12) Allen, D.; Callaghan, O.; Cordier, F. L.; Dobson, D. R.;
Harris, J. R.; Hotten, T. M.; Owton, W. M.; Rathmell, R. E.;
Wood, V. A. Tetrahedron Lett. 2004, 45, 9645.
(13) Owton, W. M. Tetrahedron Lett. 2003, 44, 7147.
(14) Ho, J.-H.; Ho, T.-I. Tetrahedron Lett. 2003, 44, 4669.
(15) Cabiddu, M. G.; Cabiddu, S.; Cadoni, E.; Demontis, S.;
Fattuoni, C.; Melis, S. Tetrahedron 2002, 58, 4529.
(16) Kim, P.; Tsuruda, J. M.; Olmstead, M. M.; Eisenberg, S.;
Kurth, M. J. Tetrahedron Lett. 2002, 43, 3963.
(17) Katritzky, A. R.; Vvedensky, V. Y.; Tymoshenko, D. O.
J. Chem. Soc., Perkin Trans. 1 2001, 2483.
(18) Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011.
(19) Gallagher, T.; Pardoe, D. A.; Porter, R. A. Tetrahedron Lett.
2000, 41, 5415.
Acknowledgment
This research was partially supported by the Ministry of Education,
Science, Sports and Culture, Grant-in-Aid for Young Scientists (B),
18710066, 2006.
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Synthesis 2008, No. 13, 2089–2099 © Thieme Stuttgart · New York