M. N. Soltani Rad et al. / Tetrahedron Letters 48 (2007) 6779–6784
6783
5. Hegarty, A. F.; Tuohey, P. J. J. Chem. Soc., Perkin Trans.
2 1980, 1313–1317.
6. (a) Dowle, M. D. J. Chem. Soc., Chem. Commun. 1977,
220–221; (b) Lim, M.; Ren, W. Y.; Klein, R. S. J. Org.
Chem. 1982, 47, 4594–4595.
umn chromatography on silica gel eluting with n-hex-
ane/EtOAc (10:1).22
Acknowledgement
´
´
7. (a) Mlinaric-Majerski, K.; Margeta, R.; Veljkovic, J.
Synlett 2005, 2089–2091; (b) Maki, T.; Ishihara, K.;
Yamamoto, H. Synlett 2004, 1355–1358; (c) Mitchell, J.
A.; Reid, E. E. J. Am. Chem. Soc. 1931, 53, 321–330; (d)
Tsuji, Y.; Yamada, N.; Tanaka, S. J. Org. Chem. 1993, 58,
16–17.
We wish to thank the Shiraz University of Technology
and Shiraz University Research Councils for partial sup-
port of this work.
8. (a) Chakrabarti, J. K.; Hotten, T. M. J. Chem. Soc., Chem.
Commun. 1972, 1226–1227; (b) Clive, D. L. J. J. Chem.
Soc. (D) 1970, 1014–1015; (c) Foley, H. G.; Dalton, D. R.
J. Chem. Soc., Chem. Commun. 1973, 628–629; (d)
Tamami, B.; Kiasat, A. R. J. Chem. Res. (S) 1999, 444–
445; (e) Khan, T. A.; Pernucheralathan, S.; Ila, H.;
Junjappa, H. Synlett 2004, 2019–2021; (f) Hosseini
References and notes
1. (a) Rappoport, Z. In The Chemistry of the Cyano Group;
Wiley-Interscience: New York, 1970; (b) March, J.
Advanced Organic Chemistry, 4th ed.; John Wiley & Sons
(Asia) Ltd: Singapore, 2005.
´
Sarvari, M. Synthesis 2005, 787–790; (g) Rogic, M. M.;
Peppen, J. F. V.; Klein, K. P.; Demmin, T. R. J. Org.
Chem. 1974, 39, 3424–3426; (h) Chiou, S.; Hoque, A. K.
M. M.; Shine, H. J. J. Org. Chem. 1990, 55, 3227–
3232.
2. (a) Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V.
Angew. Chem., Int. Ed. 2005, 44, 5188–5240; (b) Serrano,
J. L.; Sierra, T.; Gonzalez, Y.; Balm, C.; Weickhardi, K.;
Magnus, A.; Moll, G. J. Am. Chem. Soc. 1995, 117, 8312–
8321; (c) Jnaneshwara, G. K.; Deshpande, V. H.; Lali-
thambika, M.; Ravindranathan, T.; Bedekar, A. V.
Tetrahedron Lett. 1998, 39, 459–462; (d) Diana, G. D.;
Cutcliffe, D.; Volkots, D. L.; Mallamo, J. P.; Bialey, T. R.;
Vescio, N.; Oglesby, R. C.; Nitz, T. J.; Wetzel, J.; Giranda,
V.; Pevear, D. C.; Dutko, F. J. J. Med. Chem. 1993, 36,
3240–3250; (e) Judkines, B. D.; Allen, D. G.; Cook, T. A.;
Evans, B.; Sardharwala, T. E. Synth. Commun. 1996, 26,
4351–4367; (f) Medwid, J. B.; Paul, R.; Baker, J. S.;
Brockman, J. A.; Du, M. T.; Hallett, W. A.; Hanifin, J.
W.; Hardy, R. A.; Tarrant, M. E.; Torley, L. W.; Wrenn,
S. J. Med. Chem. 1990, 33, 1230–1241.
9. (a) Kuo, C. W.; Zhu, J. L.; Wu, J. D.; Chu, C. M.; Yao, C.
F.; Shia, K. S. Chem. Commun. 2007, 301–303; (b) Saedny,
A. Synthesis 1985, 184–185, and references cited therein.
10. (a) Mori, K.; Yamaguchi, K.; Mizugaki, T.; Ebitani, K.;
Kaneda, K. Chem. Commun. 2001, 461–462; (b) Chen, F.
E.; Peng, Z. Z.; Fu, H.; Liu, J. D.; Shao, L. Y. J. Chem.
Res. (S) 1999, 726–727; (c) Iida, S.; Tego, H. Synlett 2007,
407–410; (d) Iida, S.; Tego, H. Synlett 2006, 2633–2635; (e)
De luca, L.; Giacomelli, G. Synlett 2004, 2180–2184; (f)
Chen, F. E.; Kuang, Y. Y.; Dai, H. F.; Lu, L.; Huo, M.
Synthesis 2003, 2629–2631.
11. Elkaim, L.; Gacon, A. Tetrahedron Lett. 1997, 38, 3391–
3394.
3. (a) Soli, E. D.; Manoso, A. S.; Patterson, M. C.; Deshong,
P. J. Org. Chem. 1999, 64, 3171–3177; (b) Lian-Hua, L.;
Zhen-Liang, P.; Xin-Hua, D.; Yong-Min, L. Synlett 2006,
2094–2098; (c) Friedman, L.; Shechter, H. J. Org. Chem.
1960, 25, 877–879; (d) Thoman, C. J.; Habeeb, T. D.;
Huhn, M.; Korpusik, M.; Slish, D. F. J. Org. Chem. 1989,
54, 4476–4478; (e) Regen, S. L.; Quici, S.; Liawa, S. J. J.
Org. Chem. 1979, 44, 2029–2030; (f) Harusawa, S.;
Yoneda, R.; Omori, Y.; Kurihara, T. Tetrahedron Lett.
1987, 28, 4189–4190; (g) Cook, F. L.; Bowers, C. W.;
Liotta, C. L. J. Org. Chem. 1974, 39, 3416–3418; (h)
Zieger, H. E.; Wo, S. J. Org. Chem. 1994, 59, 3838–3840;
(i) Smiley, R. A.; Arnold, C. J. Org. Chem. 1960, 25, 257–
258; (j) Lewis, R. N.; Susi, P. V. J. Am. Chem. Soc. 1952,
74, 840–841; (k) Buehler, C. A.; Pearson, D. E., Survey of
Organic Synthesis, Wiley-Interscience: New-York, 1977;
Vol. 2, Chapter 19.
4. (a) Toland, W. G. J. Org. Chem. 1962, 27, 869–871; (b)
Gelas-Mialhe, Y.; Vessiere, R. Synthesis 1980, 1005–1007;
(c) Das, B.; Madhusudhan, P.; Venkataiah, B. Synlett
1999, 1569–1570; (d) Karmarkar, S. N.; Kelkar, S. L.;
Wadia, M. S. Synthesis 1985, 510–512; (e) Miller, M. J.;
Loudon, G. M. J. Org. Chem. 1975, 40, 126–127; (f)
Smith, R. F.; Walker, L. E. J. Org. Chem. 1962, 27, 4372–
4375; (g) Arote, N. D.; Bhalerao, D. S.; Akamanchi, K. G.
Tetrahedron Lett. 2007, 48, 3651–3653; (h) Sharghi, H.;
Hosseini Sarvari, M. Tetrahedron 2002, 58, 10323–10328;
(i) Carmeli, M.; Shefer, N.; Rozen, S. Tetrahedron Lett.
2006, 47, 8969–8972; (j) Movassagh, B.; Shokri, S.
Tetrahedron Lett. 2005, 46, 6923–6925; (k) Wang, E. C.;
Lin, G. J. Tetrahedron Lett. 1998, 39, 4047–4050; (l)
Ballini, R.; Fiorini, D.; Plamieri, A. Synlett 2003, 1841–
1843; (m) Bandgar, B. P.; Makone, S. S. Synlett 2003,
262–264.
12. Kato, Y.; Ooi, R.; Asano, Y. J. Mol. Catal. B: Enzym.
1999, 6, 249–256.
13. Hooz, J.; Linke, S. J. Am. Chem. Soc. 1968, 90, 6891–
6892.
14. (a) Castro, B. R. Org. React. 1983, 29, 1–162; (b)
Grundman, C. In Methoden der Organischen Chemie
(Houben-Weyl); Georg Thieme: Stuttgart, Germany,
1985; Vol. E5, p 1474; (c) Biogegrain, R.; Castro, B.;
Selve, C. Tetrahedron Lett. 1975, 30, 2529–2530; (d)
Schwartz, M. A.; Zoda, M.; Vishnuvajjala, B.; Mami, I.
J. Org. Chem. 1976, 41, 2502–2503; (e) Camps, F.; Gasol,
V.; Guerrero, A. Synth. Commun. 1988, 18, 445–452.
15. (a) Mitsunobu, O. Synthesis 1981, 1–28; (b) Hughes, D. L.
Org. React. 1992, 42, 358–359; (c) Loibner, H.; Zbiral, E.
Helv. Chim. Acta 1976, 59, 2100–2113.
16. (a) Bogdan, K. W. Synth. Commun. 1993, 23, 2481–2484;
(b) Aesa, M. C.; Baan, G.; Novak, L.; Szantay, C. Synth.
Commun. 1995, 25, 2575–2578.
17. (a) Brett, D.; Dowine, I. M.; Lee, J. B. J. Org. Chem. 1967,
32, 855–856; (b) Mizuno, A.; Hamada, Y.; Shioiri, T.
Synthesis 1980, 1007–1009; (c) Iranpoor, N.; Firouzabadi,
H.; Akhlaghinia, B.; Nowrouzi, N. J. Org. Chem. 2004, 69,
2562–2564.
18. (a) Davis, R.; Untch, K. G. J. Org. Chem. 1981, 46, 2985–
2987; (b) Kanai, T.; Kanagawa, Y.; Ishii, Y. J. Org. Chem.
1990, 55, 3274–3277.
19. (a) Iida, S.; Togo, H. Synlett 2007, 407–410; (b) Iida, S.;
Togo, H. Synlett 2005, 1456–1458.
20. Soltani Rad, M. N.; Behrouz, S.; Khalafi-Nezhad, A.
Tetrahedron Lett. 2007, 48, 3445–3449.
21. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemis-
try, Part A, 2nd ed.; Plenum Press: New York, 1985; p
265.