Y. Riadi et al. / Tetrahedron Letters 52 (2011) 3492–3495
3495
Table 4
15. Beebe, X.; Wodka, D.; Sowin, T. J. J. Comb. Chem. 2001, 3, 360–366.
16. Hari, A.; Karan, C.; Rodrigues, W. C.; Miller, B. L. J. Org. Chem. 2001, 66, 991–996.
2
Studies on the reuse of ZnBr /ABM
17. Pottorf, R. S.; Chadha, N. K.; Katkevics, M.; Ozola, V.; Suna, E.; Ghane, H.;
Round
Yield in 4aa (%)
2
ZnBr /ABM recovered (%)
Regberg, T.; Player, M. R. Tetrahedron Lett. 2003, 44, 175–178.
1
1
8. Chen, F.; Shen, C.; Yang, D. Tetrahedron Lett. 2011, 52, 2128–2131.
9. Chua, M.-S.; Shi, D.-F.; Wrigley, S.; Bradshaw, T. D.; Hutchinson, I.; Shaw, P. N.;
Barrett, D. A.; Stanley, L. A.; Stevens, M. F. G. J. Med. Chem. 1999, 42, 381–392.
0. Kashiyama, E.; Hutchinson, I.; Chua, M.-S.; Stinson, S. F.; Phillips, L. R.; Kaur, G.;
Sausville, E. A.; Bradshaw, T. D.; Westwell, A. D.; Stevens, M. F. G. J. Med. Chem.
1
2
3
4
5
6
96
95
91
88
85
79
99
97
93
93
91
86
2
1999, 42, 4172–4184.
21. Hutchinson, I.; Chua, M.-S.; Browne, H. L.; Trapani, V.; Bradshaw, T. D.;
Westwell, A. D.; Stevens, M. F. G. J. Med. Chem. 2001, 44, 1446–1455.
a
Each reaction was carried out as described in reference.36
2
2
2. Leng, W.; Zhou, Y.; Xu, Q.; Liu, J. Macromolecules 2001, 34, 4774–4779.
3. Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. R.; Westwell, A. D.; Stevens, M.
F. G. J. Med. Chem. 2002, 45, 744–747.
2
4. Moghaddam, F. M.; Bardajee, G. R.; Ismaili, H.; Dokht Taimoory, S. M. Synth.
catalytic processes and reduced environmental problems (lower
energy, valorization of a waste as natural and reusable catalyst,
non-toxicity of the catalyst, reduced amount of solvent).
Commun. 2006, 36, 2543–2548.
25. Park, K. H.; Jun, K.; Shin, S. R.; Oh, S. W. Tetrahedron Lett. 1996, 37, 8869–8870.
26. Varma, R. S.; Saini, R. K.; Prakash, O. Tetrahedron Lett. 1997, 38, 2621–2622.
2
2
7. Chang, J.; Zhao, K.; Pan, S. Tetrahedron Lett. 2002, 43, 951–954.
8. Praveen, C.; Kumar, K. H.; Muralidharan, D.; Perumal, P. T. Tetrahedron 2008,
Acknowledgment
6
4, 2369–2374.
2
3
3
9. Brink, G. J.; Arends, W. C. E., I; Sheldon, R. A. Chem. Rev. 2004, 104, 4105–4123.
0. Beller, M. Adv. Synth. Catal. 2004, 346, 107–108.
1. Kawashita, Y.; Nakamichi, N.; Kawabata, H.; Hayashi, M. Org. Lett. 2003, 5,
The authors thank the Hubert Curien ‘‘Volubilis’’ Program for
financial support.
3
713–3715.
2. Chen, Y. X.; Qian, L. F.; Zhang, W.; Han, B. Angew. Chem., Int. Ed. 2008, 47, 9330–
333.
3
9
References and notes
3
3. Songnian, L.; Lihu, Y. Tetrahedron Lett. 2005, 46, 4315–4319.
3
4. Riadi, Y.; Mamouni, R.; Abrouki, Y.; El Haddad, M.; Saffaj, N.; El Antri, S.;
Routier, S.; Guillaumet, G.; Lazar, S. Lett. Org. Chem. 2010, 7, 269–271.
5. Riadi, Y.; Mamouni, R.; Azzalou, R.; Boulahjar, R.; Abrouki, Y.; El Haddad, M.;
Routier, S.; Guillaumet, G.; Lazar, S. Tetrahedron Lett. 2010, 51, 6715–6717.
6. Sebti, S.; Tahir, R.; Nazih, R.; Boulaajaj, S. Appl. Catal. 2001, 218, 25–30.
7. General procedure for the synthesis 3–5: The catalyst (100 mg) was added to a
mixture of aldehyde 2 (1.1 mmol) and o-phenylenediamine 1a, o-aminophenol
1
2
.
.
Chen, C.; Chen, Y. J. Tetrahedron Lett. 2004, 45, 113–115.
Siddiqui, N.; Rana, A.; Khan, S. A.; Bhat, M. A.; Haque, S. E. Bioorg. Med. Chem.
Lett. 2007, 17, 4178–4182.
Lion, C. J.; Matthews, C. S.; Wells, G.; Bradshaw, T. D.; Stevens, M. F. G.;
Westwell, A. D. Bioorg. Med. Chem. Lett. 2006, 16, 5005–5008.
Huang, S. T.; Hsei, I. J.; Chen, C. Bioorg. Med. Chem. 2006, 14, 6106–6119.
Girardet, J.-L.; Townsend, L. B. J. Org. Chem. 1999, 64, 4169–4172.
Yeh, C.-M.; Tung, C.-L.; Sun, C.-M. J. Comb. Chem. 2000, 2, 341–348.
Chen, J. J.; Wei, Y.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2000, 43, 2449–
3
3
.
3
3
4
5
6
7
.
.
.
.
1
b or o-aminothiophenol 1c (1.0 mmol). The mixture was stirred at 111 °C in
the presence of 5 mL toluene. Progress of the reaction was monitored by TLC
n-hexane/EtOAc 2:1). After complete conversion, the reaction mixture was
(
2
456.
filtered, the catalyst was washed, and the solvent was removed under reduced
pressure. The crude material was purified by column chromatography or
recrystallization to afford the pure product 3, 4 or 5.
8
9
.
.
Tumelty, D.; Cao, K.; Holmes, C. P. Org. Lett. 2001, 3, 83–86.
Mann, J.; Baron, A.; Opoku-Boahen, Y.; Johansson, E.; Parkinson, G.; Kelland, L.
R.; Neidle, S. J. Med. Chem. 2001, 44, 138–144.
3
3
4
4
8. Devalla, V. R.; Ethirajulu, K. J. Chem. Soc. 1995, 1497–1501.
9. Bougrin, K.; Loupy, A.; Soufiaoui, M. Tetrahedron 1998, 54, 8055–8064.
0. Naidu, A. B.; Sekar, G. Synthesis 2010, 579–586.
1
1
1
1
0. Raju, B.; Nguyen, N.; Holland, G. W. J. Comb. Chem. 2002, 4, 320–328.
1. Akamatsu, H.; Fukase, K.; Kusumoto, S. J. Comb. Chem. 2002, 4, 475–483.
2. Hoesl, C. E.; Nefzi, A.; Houghten, R. A. J. Comb. Chem. 2003, 5, 155–160.
3. Vourloumis, D.; Takahashi, M.; Simonsen, K. B.; Ayida, B. K.; Barluenga, S.;
Winters, G. C.; Hermann, T. Tetrahedron Lett. 2003, 44, 2807–2811.
4. Shi, D.-F.; Bradshaw, T. D.; Wrigley, S.; McCall, C. J.; Lelieveld, P.; Fichtner, I.;
Stevens, M. F. G. J. Med. Chem. 1996, 39, 3375–3384.
1. Balaji, S. L.; Umesh, R. P.; Jyotirling, R. M.; Ramrao, A. M. Bull. Korean Chem. Soc.
2010, 31, 2329–2332.
1