An Efficient Method for the Chemoselective Synthesis of Germinal Diacetates from Aromatic and Heteroaromatic Aldehydes Using Nano Silica Chloride

Document Type : Research Paper

Authors

1 Applied Biotechnology Research Center, Baqiyatallah University of Medical Sciences, Tehran, Iran

2 Department of Chemistry, Faculty of Science, Zanjan University, P.O. Box 45195-313 Zanjan, I.R. Iran

10.7508/jns.2013.04.001

Abstract

In this investigation, Nano silica chloride (nano SiO2Cl) has been found to be efficient, chemoselective and recyclable catalyst for facile and simple synthesis of germinal diacetates from aromatic and heteroaromatic aldehydes in shorter reaction durations. The products were obtained in high to excellent yields. This work consistently has the advantages of excellent yields, short reaction time, mild condition and work-up procedures. This method might be useful in the future for the preparation of similar derivatives.

Keywords

References

[1] T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, third ed. (John Wiley and Sons, New York 1999, p. 306) (b) M.J. Gregory, J. Chem. Soc. B (1970) 1201-1207.
[2] (a) R.E. Banks, J.A. Miller, M.J. Nunn, P. Stanley, T.R. Weakley, J. Ullah, J. Chem. Soc., Perkin Trans.1 (1981) 1096-1102. (b) B.B. Snider, S.G. Amin, Synth. Commun. 8 (1978) 117-125.
[3] (a) G.M. Whitesides, J.S. Filippo. J. Am. Chem. Soc. 92 (1970) 6611-6624. (b) J.G. Frick, R.J. Harper, J. Appl. Polym. Sci. 29 (1984) 1433-1447.
[4] M.J. Gregory, J. Chem. Soc. (1970) 1201-1207.
[5] F. Freeman, E.M. Karcherski, J. Chem. Eng. Data 22 (1977) 355-357.
[6] T.S. Jin, G. Sun, Y.W. Li, T.S. Li, Green Chem. 4 (2002) 255-256.
[7] H.M.S. Kumar, B.V.S. Reddy, P.T. Reddy, J.S. Yadav, J. Chem. Res. (S) (2000) 86-89.
[8] S. Gowravaram, S. Abraham, T. Ramalingam, J.S. Yadav, J. Chem. Res. (S) 3 (2002) 144-147.
[9] T.S. Jin, G.Y. Du, T.S. Li, Ind. J. Chem., Sect. B 37 (1998) 939-940.
[10] J.K. Michie, J.A. Miller, Synthesis (1981) 824-825.
[11] C. Wang, M. Li, Synth. Commun. 32 (2002) 3469-3473.
[12] B. Karimi, H. Seradj, R.G. Ebrahimian, Synlett (2000) 623-624.
[13] G.A. Olah, C.S. Mehrotra, Synthesis (1982) 962-963.
[14] S.V. Rajn, J. Chem. Res. (S) (1996) 68-71.
[15] M.V. Joshi, C.S. Narasimbam, J. Catal. 141 (1993) 308-310.
[16] T.S. Jin, Y.R. Ma, Z.H. Zhang, T.S. Li, Synth. Commun. 27 (1997) 3379-3383.
[17] H. Firouzabadi, N. Iranpoor, F. Nowrouzi, K. Amani, Tetrahedron Lett. 44 (2003) 3951-3954.
[18] G.P. Romanelli, H.J. Thomas, G.T. Baronetti, J. Autino, Tetrahedron Lett. 44 (2003) 1301-1303.
[19] M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, M. Nocchetti, Tetrahedron Lett. 43 (2002) 2709-2711.
[20] K.L. Chandra, P. Saravanan, V.K. Singh, Synlett (2000) 359-360.
[21] V.K. Aggarwal, S. Fonquerna, G.P. Vennall, Synlett (1998) 849-850.
[22] M.D. Carrigan, K.J. Eash, M.C. Oswald, R.S. Mohan, Tetrahedron Lett. 42 (2001) 8133-8135.
[23] B.C. Ranu, J. Dutta, A. Das, Chem. Lett. 32 (2003) 366-367.
[24] D.H. Aggen, J.N. Arnold, P.D. Hayes, N.J. Smoter, R.S. Mohan, Tetrahedron 60 (2004) 3675-3679.
[25] G. Smitha, Ch. Sanjeeva Reddy, Tetrahedron 59 (2003) 95719576.
[26] A.R. Hajipour, A. Zarei, A.E. Ruoho, Tetrahedron Lett. 48 (2007) 2881-2884.
[27] M.M. Heravi, K. Bakhtiari, F.F. Bamoharram, Catal. Commun. 7 (2006) 499-501.
[28] J.R. Satam, R.V. Jayaram, Catal. Commun. 8 (2007) 1414-1420.
[29] A.T. Khan, S. Islam, A. Majee, T. Chattopadhyay, S. Ghosh, J. Mol. Catal. A: Chem. 239 (2005) 158-165.
[30] A. Ziyaei, N. Azizi, M. R. Saidi, J. Mol. Catal. A: Chem. 238 (2005) 138-141.
[31] J.S. Yadav, B.V.S. Reddy, P. Sreedhar, G. Kondaji, K. Nagaiah, Catal. Commun. 9 (2008) 590-593.
[32] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Catal. Commun. 9 (2008) 89-96.
[33] R. Ballini, M. Bordoni, G. Bosica, R. Maggi, G. Sartori, Tetrahedron Lett. 39 (1998) 7587-7590.
[34] Y. Jin, J. Shi, F. Zhang, Y. Zhong, W. Zhu, Journal of Molecular Catalysis A: Chemical 383-384 (2014) 167-171.
[35] J.K. Augustine, A. Bombrun, W.H.B. Sauer, P. Vijaykumar, Tetrahedron Lett. 53 (2012) 5030-5033.
[36] (a) M. Yadegari, M. Moghadam, Sh. Tangestaninejad, V. Mirkhani, I. Mohammadpoor, Inorganica Chimica Acta 388 (2012) 102-105. (b) S. Krompiec, M. Penkala, K. Szczubiałka, E. Kowalska, Coordination Chemistry Reviews, 256 (2012) 2057-2095.
[37] R. Karimian, F. Piri, B. Karimi, A. Moghimi, Croat. Chem. Acta 84 (2011) 111-115.
[38] R. Karimian, F. Piri, B. Karimi, A. Moghimi, Chin. J. Chem. 29 (2011) 2421-2427.
Journal of Nanostructures
Volume 3, Issue 4 - Serial Number 4
December 2013
Pages 387-393

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