2564
X.-Y. Ma et al. / Tetrahedron 69 (2013) 2560e2564
was directly evaporated to dryness and the residue was purified by
column chromatography on silica gel (ethyl acetate/n-
5. (a) Kazemi, F.; Kiasat, A. R.; Fadavipoor, E. Phosphorus, Sulfur Silicon Relat. Elem.
004, 179, 433e436; (b) Olah, G. A.; Narang, S. C.; Garcia-Luna, A. Synthesis
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5184e5187.
2
1
1
hexane¼1:15) to give furan-2-carbonitrile as a colourless liquid
1
(
1
93 mg, 50%). H NMR (500 MHz, CDCl
3
):
d
6.55 (m, 1H), 7.12 (m,
2
9
H), 7.60 (m, 1H). Data are in good agreement with the literature.
7. Yadav, L. D. S.; Srivastava, V. P.; Patel, R. Tetrahedron Lett. 2009, 50, 5532e5535.
8
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4.2.13. Thiophene-2-carbonitrile (Table 2, entry 12). To a 25 mL
round-bottom flask equipped with magnetic stirrer were added
thiophene-2-carbaldehyde oxime (254 mg, 2 mmol), cupric acetate
(
2
Cu(OAc) ) 36 mg (0.2 mmol) and acetonitrile (5 mL). The mixture
was heated to reflux for 0.25 h. After cooling to room temperature,
the solution was directly evaporated to dryness and the residue was
purified by column chromatography on silica gel (ethyl acetate/n-
9. (a) Zuidema, D. R.; Dennison, A. L.; Park, E. Y.; Mebane, R. C. Synth. Commun.
008, 38, 3810e3815; (b) Li, Y.-T.; Liao, B.-S.; Chen, H.-P.; Liu, S.-T. Synthesis
2011, 2639e2643.
2
hexane¼1:15) to give thiophene-2-carbonitrile as a colourless liquid
1
(
7
143 mg, 61%). H NMR (500 MHz, CDCl
3
):
d
7.14 (m,1H), 7.62 (m,1H),
10. (a) Ping, Y.; Batamack, P.; Prakash, G.; Olah, G. Catal. Lett. 2005, 101, 141e143; (b)
2
3
.65 (m, 1H). Data are in good agreement with the literature.
Allen, C. L.; Burel, C.; Williams, J. M. J. Tetrahedron Lett. 2010, 51, 2724e2726.
11. Yang, S. H.; Chang, S. Org. Lett. 2001, 3, 4209e4211.
1
2. Makarycheva-Mikhailova, A. V.; Bokach, N. A.; Haukka, M.; Kukushkin, V. Y.
Inorg. Chim. Acta 2003, 356, 382e386.
Acknowledgements
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3. (a) Attanasi, O.; Palma, P.; Serra-Zanetti, F. Synthesis 1983, 741e742; (b) Jiang,
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Financial support from the National Natural Science Foundation
of China-NSAF (Grant No. 11076017) is gratefully acknowledged.
14. (a) Hosseini Sarvari, M. Synthesis 2005, 787e790; (b) Enthaler, S.; Weidauer, M.;
Schr o€ der, F. Tetrahedron Lett. 2012, 53, 882e885.
1
5. Kim, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 1717e1719.
Supplementary data
16. Ramo oꢀ n, R. S.; Bosson, J.; Diíez-Gonza aꢀ lez, S.; Marion, N.; Nolan, S. P. J. Org.
Chem. 2010, 75, 1197e1202.
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These data include MOL files and InChiKeys of the most important
compounds described in this article.
1
1
1
2
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