Kiasat, Zarinderakht & Sayyahi
FULL PAPER
bined organic layer was washed with cold water (10 mL
[7] Sherrington, D. C.; Hodge, P. Synthesis and Separation Using Func-
tional Polymers, Wiley, Chichester, 1988.
×
2 4
3), dried over Na SO and evaporated in vacuo to
[
8] Dodziuk, H. Cyclodextrins and Their Complexes, Wiley-VCH Ver-
lag GmbH & Co. KGaA, Weinheim, 2006.
afford the alkyl thiocyanate in 75%—93% isolated
yields. It did not require any column chromatography
thus avoiding the possibility of rearrangement.
[
9] Villalonga, R.; Cao, R.; Fragoso, A. Chem. Rev. 2007, 107, 3088.
[
[
[
10] Takahashi, K. Chem. Rev. 1998, 98, 2013.
11] Tilloy, S.; Bricout, H.; Monflier, E. Green Chem. 2002, 4, 188.
12] Abreu, A. R.; Costa, I.; Rosa, C.; Ferreira, L. M.; Lourenco, A.;
Santos, P. P. Tetrahedron 2005, 61, 11986.
Typical procedure for the synthesis of phenacyl de-
rivatives
In a 50-mL reaction flask were placed α-bromo ke-
tone (1.0 mmol), potassium salts of thiocyanate, azide
or acetate (3 mmol), Dowex-β-CD (0.2 g) and water (5
mL). The suspension was stirred at a water bath tem-
perature of 40 ℃. The composition of the reaction
mixture was examined time by time by TLC
[13] (a) Song, L. X.; Bai, L.; Xu, X. M.; He, J.; Pan, S. Z. Coord. Chem.
Rev. 2009, 253, 1276; (b) Srinivas, B.; Kumar, V. P.; Sridhar, R.;
Reddy, V. P.; Nageswar, Y. V. D.; Rao, K. R. Helv. Chim. Acta 2009,
9
2, 1080; (c) Sridhar, R.; Srinivas, B.; Kumar, V. P.; Narender, M.;
Rao, K. R. Adv. Synth. Catal. 2007, 349, 1873; (d) Kaboudin, B.;
Sorbiun, M. Tetrahedron Lett. 2007, 48, 9015.
[14] Hapiot, F.; Tilloy, S.; Monflier, E. Chem. Rev. 2006, 106, 767.
[15] Siu, M.; Yaylayan, V. A.; Belanger, J. M. R.; Pare, J. R. J. Tetrahe-
dron Lett. 2005, 46, 3737.
[
V(n-hexane)∶V(ethylacetate)=5∶1]. After comple-
tion of the reaction, the catalyst was removed via filtra-
tion and the filtrate was extracted with acetonitrile (5
[
16] Wang, Y.; Xiao, Y.; Tan, T. T. Y.; Ng, S. C. Tetrahedron Lett. 2008,
9, 5190.
4
mL×3). The organic phases were dried over CaCl and
2
[
17] Lagrost, C.; Alcaraz, G.; Bergamini, J. F.; Fabre, B.; Serbanescu, I.
then evaporated to dryness to give desired product. The
crude products were purified by either preparative TLC
or flash chromatography.
Chem. Commun. 2007, 1050.
[18] Li, X.; Qi, Z.; Liang, K.; Bai, X.; Xu, J.; Liu, J.; Shen, J. Catal. Lett.
008, 124, 413.
2
[
[
19] Kiasat, A. R.; Sayyahi, S. Catal. Commun. 2010, 11, 484.
20] Guy, R. G. The Chemistry of the Cyanates and Their Thio Deriva-
tives, Ed.: Patai, S., Wiley Interscience, New York, 1977, p. 819.
21] Kamal, A.; Chouhan, G. Tetrahedron Lett. 2005, 46, 1489.
22] Ju, Y.; Kumar, D.; Varma, R. S. J. Org. Chem. 2006, 71, 6697.
23] Kiasat, A. R.; Badri, R.; Sayyahi, S. Chin. Chem. Lett. 2008, 19,
Acknowledgment
[
[
[
The authors gratefully acknowledge the funding
support received for this project from the Shahid
Chamran University of Ahwaz Research Council.
1
301.
24] Mokhtari, B.; Azadi, R.; Rahmani-Nezhad, S. Tetrahedron Lett.
009, 50, 6588.
[
[
2
References
25] Prakash, O.; Kaur, H.; Batra, H.; Rani, N.; Singh, S. P.; Moriarty, R.
[
1] Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.;
Sharpless, K. B. Angew. Chem. 2005, 117, 3339.
2] Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725.
3] Hailes, H. C. Org. Process. Res. Dev. 2007, 11, 114.
4] Shapiro, N.; Vigalok, A. Angew. Chem., Int. Ed. 2008, 47, 2849
5] Krishnaveni, N. S.; Surendra, K.; Rao, K. R. Adv. Synth. Catal. 2006,
M. J. Org. Chem. 2001, 66, 2019.
[26] (a) Shi, D. Q.; Zhang, S.; Zhuang, Q. Y.; Wang, X. S.; Tu, S. J.; Hu,
H. W. Chin. J. Chem. 2003, 21, 680; (b) Tverdokhlebov, A. V.;
Andrushko, A. P.; Tolmachev, A. A.; Shishkina, S. V.; Shishkin, O. V.
Synthesis 2008, 2701; (c) Majo, V. J.; Perumal, P. T. J. Org. Chem.
1998, 63, 7136.
[
[
[
[
3
48, 696.
6] (a) Kiasat, A. R.; Badri, R.; Zargar, B.; Sayyahi, S. J. Org. Chem.
008, 73, 8382; (b) Kiasat, A. R.; Fallah Mehrjardi, M. Catal.
[27] (a) Ploypradith, P.; Kagan, R. K.; Ruchirawat, S. J. Org. Chem. 2005,
70, 5119; (b) Takeuchi, H.; Yanagida, S. I.; Ozaki, T.; Hagiwara, S.;
Eguchi, S. J. Org. Chem. 1989, 54, 431; (c) Fan, X.; Zhang, Y. Tet-
rahedron Lett. 2002, 43, 1863; (d) Rao, M. L. N.; Awasthi, D. K.;
Banerjee, D. Tetrahedron Lett. 2007, 48, 431.
[
2
Commun. 2008, 9, 1497; (c) Kiasat, A. R.; Zayadi, M. Catal. Com-
mun. 2008, 9, 2063.
(Cheng, F.)
702
www.cjc.wiley-vch.de
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2012, 30, 699—702