A Mild and Efficient Method for the Chemoselective Synthesis of Acylals from Aromatic Aldehydes and their Deprotections Catalyzed by Sulfated Zirconia
Keywords:
Acylals, sulfated zirconia, protection, deprotectionAbstract
Abstract. Aldehydes can be converted to acylals by treatment with acetic anhydride in the presence of sulfated zirconia in excellent yield at 0 oC. Ketones and aliphatic aldehydes are found to be unaffected under the reaction conditions. The deprotection of the resulting acylals is achieved using the same catalyst at 60 oC. The catalyst can be reused in two cycles without losing its activity.
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References
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2. Kochhar, K.S.; Bal, B.S.; Deshpande, R.P.; Rajadhyksha, S.R.; Pinnick, H.W.; J. Org. Chem. 1983, 48, 1765.
3. Snider, B.B.; Amin, S.G.; Synth Commun. 1978, 8, 117.
4. Trost, B.M.; Lee, C.B.; J. Am. Chem. Soc. 2001, 123, 3687.
5. Yadav, J.S.; Reddy, B.V.S.; Madhuri, Ch.; Sabitha, G.; Chem. Lett. 2001, 18.
6. Carrigan, M.C.; Eash, K.J.; Oswald, M.C.; Mohan, R.S.; Tetrahedron Lett. 2001, 42, 8133.
7. Aggen, D.H.; Hayes, Arnold, J.N.; Hayes, P.D.; Smoter, N.J.; Mohan, R.S.; Tetrahedron 2004, 60, 3675.
8. Smitha, G.; Reddy, Ch.S.; Tetrahedron 2003, 59, 9751, and references cited therein.
9. Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F.; Amani, K.; Tetrahedron Lett. 2003, 44, 3951.
10. Ranu, B.C.; Dutta, J.; Das, A.; Chem. Lett. 2003, 32, 366.
11. Karimi, B.; Maleki, J.; J. Org. Chem. 2003, 68, 4951.
12. Roy, S.C.; Banerjee, B.; Synlett 2002, 1677.
13. Yadav, J.S.; Reddy, B.V.S.; Srinivas, Ch.; Synth. Commun. 2002, 32, 2169.
14. Jin, T.-S.; Sun, G.; Li, Y.-W.; Li, T.-S.; Green Chem. 2002, 4, 255.
15. Sumida, N.; Nishioka, K.; Sato, T.; Synlett 2001, 12, 1921.
16. Chandra, K.L.; Saravanan, P.; Singh, V.K.; Synlett 2000, 359
17. Gregory, M.J.; J. Chem. Soc. B 1970, 1201.
18. Michie, J.K.; Miller, J.A.; Synthesis 1981, 824.
19. Karimi, B.; Seradj, H.; Ebrahimian, R.G.; Synlett 2000, 623.
20. Deka, N.; Kalita, D. J.; Borah, R.; Sarma, J.C.; J. Org. Chem. 1997, 62, 1563.
21. Agarwal, V.K.; Fonquerna, S.S.; Vennall, G.P.; Synlett 1998, 849.
22. Deka, N.; Borah, R.; Kalita, D.J.; Sarma, J.C.; J. Chem. Res. (S) 1998, 94.
23. Jin, T.-S.; Du, G.-Y.; Li, T.-S.; Ind. J. Chem., Sect. B 1998, 939.
24. Wang, C.; Li. M.; Synth. Commun. 2002, 32, 3469.
25. Gowravaram, S.; Abraham S.; Ramalingam, T.; Yadav, J.S.; J. Chem. Res. (S) 2002, 3, 144.
26. Olah, G.A.; Mehrotra, A.K.; Synthesis 1982, 962.
27. Kumar, P.; Hegde, V.R.; Kumar, T.P.; Tetrahedron Lett. 1995, 36, 601; Pereira, C.B.; Gigante, M.J.; Marcelo-Curto, H.; Carreyre, G.; Perot, G.; Guisnet, M.; Synthesis 1995, 1077; Ballini, R.; Bordoni, M.; Bosica, G.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1998, 39, 7587.
28. Li, T.S.; Zhang, Z.H.; Gao, Y.J.; Synth. Commun. 1998, 28, 4655 ; L’uboš, J.; Komadel, P.; J. Catal. 2003, 218, 227.
29. Bandgar, B. P.; Makone, S.S.; Kulkarni, S.P.; Monatsh. Chem. 2000, 131, 417.
30. Reddy, A.V.; Ravinder, K.; Reddy, V.L.N.; Ravikanth, V.; Yenkateswarlu, Y.; Synth. Commun. 2003, 33, 1531.
31. Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O.; Nocchetti, M.; Tetrahedron Lett. 2002, 43, 2709.
32. Benjaram, M.R.; Pavani, M.S.; Tetrahedron Lett. 2003, 44, 4447.
33. Negrón, G.; Angeles, D.; Lomas, L.; Martínez, A.; Ramírez, M.; Martínez, R.; Heterocycles. 2004, 63, 367.
34. Deutsch, J.; Trunschke, A.; Muller, D.; Quaschning, V.; Kemnitz, E.; Lieske, H.; Catalysis Lett. 2003, 88, 9.
35. Toshima, K.; Nagai, H.; Kasumi, K.; Kawahara, K.; Matsumura, S.; Tetrahedron 2004, 60, 5331.
36. Satya V.; Raju, N.; J. Chem. Research 1996, 68.
37. Song, X.; Sayari, A.; Catal. Rev. 1996, 38, 329.
38. Davis, B.H.; Keogh, R.; Srinivasan, R.; Catal. Today 1994, 20, 219.
39. Ku, Y.-Y.; Patel, R.; Sawick, D.; Tetrahedron Lett. 1993, 34, 8037.
40. Mohammadpoor-Baltrok, I.; Aliyan, H.; Synt. Commun. 1999, 29, 2741.
41. Ramalingam, T.; Srinivas, R.; Reddy, B.V.S.; Yadav, J.S.; Synt. Commun. 2001, 31, 1091.
42. Reddy, B.M.; Reddy, V.R.; Mater. Sci. Lett. 2000, 19, 763; Reddy, B.M.; Sreekanth, P.M.; Yamada, Y.; Xu, Q.; Kobayashi, T.; Appl. Catal. A : General 2000, 228, 269; Zhao, Y.; Zhang, W.L.M.; Tao, K.; Cat. Comm. 2002, 3, 2039.
43. Balina, G.B.; Kesler, P.; Petre, J.; Pham, D.; Vollmar, A.; J. Org. Chem. 1986, 51, 3811.
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