2428
N. Hergu e´ et al. / Tetrahedron Letters 49 (2008) 2425–2428
the utilization of the triflate group, the synthesis of 3-
substituted thieno[3,2-b]furans was also achieved.
15. Sugiyama, H.; Yoshida, M.; Mori, K.; Kawamoto, T.; Sogabe, S.;
Takagi, T.; Oki, H.; Tanaka, T.; Kimura, H.; Ikeura, Y. Chem.
Pharm. Bull. 2007, 55, 613.
1
1
6. Gewald, K.; Bellmann, P. J. Prakt. Chem. 1983, 325, 457.
7. Banks, M. R.; Barker, J. M.; Huddleston, P. R. J. Chem. Soc., Perkin
Trans. 1 1986, 2223.
Acknowledgment
The authors thank the SCAS of the University of
Angers for analytical characterization.
18. Beck, J. R. J. Heterocycl. Chem. 1975, 12, 1037.
1
9. Gillespie, R. J.; Murray-Rust, J.; Murray-Rust, P.; Porter, A. E. A. J.
Chem. Soc., Chem. Commun. 1979, 366.
2
0. All new compounds exhibited spectral properties consistent with the
assigned structures.
Supplementary data
Selected examples:
1
Compound 1: White solid, mp 220 °C, dec H NMR (500 MHz,
1
13
Evolution of the H NMR spectrum of 6 in CDCl .
CDCl
NMR (125.7 MHz, CDCl
38.7, 156.1, 162.4; MS (EI) 256 [M ].
Compound 8: White solid, dec from 210 °C. H NMR (500 MHz,
3
) 3.93 (s, 3H), 4.00 (s, 3H), 7.67 (s, 1H), 8.2 (br s, 1H);
C
3
) 52.2, 52.7, 89.3, 116.8, 117.6, 119.6, 130.5,
3
+Å
1
1
13
CDCl
CDCl
1
3
) 3.95 (s, 3H), 4.01 (s, 3H), 7.06 (s, 1H); C NMR (125.7 MHz,
1
3
) 52.8, 52.9, 116.6, 117.2 (q,
JC–F = 321 Hz), 120.5, 136.7,
38.8, 139,3, 155.5, 157.2, 161,7; MS (EI) 388 [M ].
Compound 9: White solid, mp 112 °C, H NMR (500 MHz, CDCl
+Å
References and notes
1
3
)
3
.93 (s, 3H) and 3.97 (s, 3H), 7.52 (s, 1H), 7.77 (s, 1H); MS (EI) 240
+Å
1. Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
[M ].
1
2. Chakraborty, T. K.; Arora, A.; Roy, S.; Kumar, N.; Maiti, S. J. Med.
Chem. 2007, 50, 5539.
Compound 10: White solid, mp 131–132 °C. H NMR (500 MHz,
CDCl ) 3.75 (s, 3H), 3.93 (2s, 5H), 3.98 (s, 3H), 7.73 (s, 1H);
1
3
3
C
3
4
. Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411.
. Gandini, A.; Belgacem, M. N. Prog. Polym. Sci. 1997, 22,
3
NMR (125.7 MHz, CDCl ) 34.7, 52.4, 52.7, 53.0, 116.5, 124.8, 129.5,
+Å
137.8, 143.5, 156.4, 159.0, 162.2, 168.8; MS (EI) 344 [M ].
1
1203.
Compound 11: White solid, mp 157 °C. H NMR (500 MHz, CDCl )
3
3
3
5
6
. Lasseuguette, E.; Gandini, A.; Belgacem, M. N.; Timpe, H. J.
Polymer 2005, 46, 5476.
. Benahmed-Gasmi, A.; Fr e` re, P.; Roncali, J. J. Electroanal. Chem.
3.95 (s, 3H), 4.02 (s, 3H), 7.20 (dd, 1H, J = 5.2 Hz, J = 3.7 Hz); 7.53
(d, J = 5.2 Hz), 7.78 (s, 1H), 7.89 (d, 1H, J = 3.7 Hz); C NMR
3
3
13
(125.7 MHz, CDCl ) 52.5, 52.8, 116.6, 127.7, 128.4, 128.6, 129.0,
3
+Å
1996, 406, 231.
130.4, 130.9, 138.0, 141.5, 155.7, 159.6, 162.5; MS (EI) 322 [M ].
7
8
9
. Fr e` re, P.; Skabara, P. Chem. Soc. Rev. 2005, 34, 69.
. McCallion, G. Curr. Org. Chem. 1999, 3, 67.
. Paulmier, C.; Morel, J.; Semard, D.; Pastour, P. Bull. Soc. Chim. Fr.
21. Cappon, B.; Kwok, F. C. Tetrahedron 1987, 43, 69.
22. Dahlen, K.; Wallen, E. A. A.; Grotti, M.; Luthman, K. J. Org. Chem.
2006, 71, 6863.
1
973, 7–8, 2434.
23. Lopez, O. D.; Goodrich, J. T.; Yang, F.; Snyder, L. B. Tetrahedron
Lett. 2007, 48, 2063.
1
0. Black, M.; Cadogan, J. I. G.; McNab, H.; MacPherson, A. D.;
Roddam, V. P.; Smith, C.; Swenson, H. R. J. Chem. Soc., Perkin
Trans. 1 1997, 2483.
3
24. Crystallographic data for 9: Crystal size (0.29 Â 0.14 Â 0.02 mm ),
C
1
0 8 5 r
H O S, M = 240.22, orthorhombic, space group P bcm,
1
1
1
1
1. Svoboda, J.; Nic, M.; Palecek, J. Collect. Czech. Chem. Commun.
a = 13.5456(8) A˚ , b = 11.5419(9) A˚ , c = 6.6921(4) A˚ , a = b = c =
90°, V = 1046(26) A˚ , Z = 4, q
3
3
1993, 58, 2983.
calcd
= 1.525 g/cm , 12,836 reflections
2. Svoboda, J.; Pihera, P.; Sedmera, P.; Palecek, J. Collect. Czech. Chem.
Commun. 1996, 61, 888.
3. Machara, A.; Kurf u¨ rst, M.; Kozmik, V.; Petrickova, H.; Dvorakova,
H.; Svoboda, J. Tetrahedron Lett. 2004, 45, 2189.
4. Pankiewicz, J.; Decroix, B.; Morel, J. C.R. Acad. Sci., Paris 1975, 281,
C-39–C-41.
collected in the 3–27° h range, 1253 independent reflections from
which 534 with I > 2r(I) converged to R = 0.0523 and wR2 (all
data) = 0.1413 with 98 parameters, GOF = 0.892.
Crystallographic data excluding structure factors have been deposited
with the Cambridge Crystallographic Data under reference CCDC:
669379.