Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran

2 Chemistry Department, Qaemshahr Branch, Islamic Azad University, Qaemshahr, I. R. Iran

Abstract

1,1-Diacetates(acylals) were prepared by direct condensation of various aldehydes with acetic anhydride using dipyridine cobalt chloride (CoPy2Cl2) as an efficient and green catalyst under solvent-free conditions at room temperature. The important features of this catalyst method are that the catalyst is solid, stable at high temperatures, soluble in water, stable in air, immiscible in common organic solvents, low toxic and, above all, it is reusable. CoPy2Cl2 can be recycled after a simple work-up and reused at least five runs without appreciable loss of its catalytic activity. High chemo-selectivity toward aldehyde in the presence of ketones is another advantage of the present method which provides selective protection of aldehydes in their mixtures with ketones.

Graphical Abstract

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[1] T.W. Greene, P.G.M. Wuts, Wiley: New York, 1991.

[2] M.J.J. Gregory, Chem. Soc., 1970, (B), 1201-1207.

[3] H.W. Pinnick, K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N.J. Radhakrishna, Org. Chem., 1983, 48, 1765-1767.

[4] H. Held, A. Rengstle, D. Mayer, Gerhartz, New York, 1985, A1, 68.

[5] J.G. Frick, R.J. Harper, J. Appl. Polym. Sci., 1984, 1433.

[6] W.R. Eanderson, Eur. Pat. Appl. EP 125, 781; Chem. Abstr., 1985, 103, P64010K.

[7] B. Karimi, J.J. Maleki, Org. Chem., 2003, 68, 4951-4954.

[8] J.S. Yadav, B.V.S. Reddy, Ch. Srinivas, Synth. Commun., 2002, 32, 2169-2174.

[9] M.J.J. Gregory, Chem. Soc. (B), 1970, 1201-1207.

[10] B. Karimi, H. Seradj, G.R. Ebrahimian, Synlett., 2000, 5, 623-624.

[11] S.C. Roy, B. Banerjee, Synlett., 2002, 1677-1678.

[12] N. Deka, R. Borah, D.J. Kalita, J.C.J. Sarma, Chem. Res., 1998, (S), 94-95.

[13] N. Deka, D.J. Kalita, R. Borah, J.C.J. Sarma, Org. Chem., 1997, 62, 1563-1564.

[14]J.K. Michie, J.A. Miller, Synthesis, 1981, 824-824.

[15] S. Sajjadifar, S. Rezayati, Chemicalpapers, 2014, 68, 531-539.

[16] S. Sajjadifar, Omid Louie, J.Chem., 2013, 2013, 6 pages.

[17] S. Sajjadifar, International Journal of ChemTech Research., 2013, 5, 385-389.

[18] S. Sajjadifar, S. Rezayati, International Journal of ChemTech Research, 2013, 5, 1964-1968.

[19] J. VenuMadhav, B. Suresh Kuarm, B. Rajitha, ARKIVOC, 2008 (ii), 204-209.

[20] M.M. Heravi, K. Bakhtiari, S. Taheri, H.A. Oskooie, Green Chem., 2005, 7, 867–869.

[21] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, CatalCommun., 2008, 9, 89–96.

[22] A.T. Khan, L.H. Choudhury, S.J. Ghosh, MolCatal A Chem., 2006, 255, 230-235.

[23] A. Saini, S. Kumar, J.S. Sandhu, Synth Commun., 2007, 38, 106–113.

[24] A.R. Hajipour, A. Zarei, A.E. Ruoho, Tetrahedron Lett., 2007, 48, 2881-2884.

[25] R. Ghosh, S. Maiti, A. Chakraborty, R. Halder, J. Mol. Catal A: Chem., 2004, 215, 49-53.

[26] N.M. Nagy, M.A. Jakab, J. Konya, and S. Antus, Appl. Clay. Sci., 2002, 21, 213-216.

[27] K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N. Raja-dhyaksha, H.W.J. Pinnick, Org. Chem.,1983, 48, 1765.

[28] H. Firouzabadi, N. Iranpoor, F. Nowrouzi, K. Amani, Tetrahedron Lett., 2003, 44, 3951.

[29] A.T. Khan, L.H. Choudhury, S. Ghosh, Eur. J. Org. Chem., 2005, 13, 2782-2787.

[30] S.A. Pourmousavi, Z. Zinati, Turk J Chem., 2009, 33, 385-392.

[31] Q. Liu, H.M. Ai, S. Feng, Synth. Commun., 2012, 42, 122-127.

[32] B. RabindranJermy, A. Pandurangan, Catal. Commun., 2008, 9, 577-583.

[33] M. NouriSefat, A. Deris, K. Niknam, Chin. J. Chem., 2011, 29, 2361-2367.

[34] A.V. Reddy, K. Ravinder, V.L.N. Reddy, V. Ravinkanth, Y. Yenkateswarlu, Synth. Commun., 2003, 33, 1531-1536.

[35]  A. Zare, A. Hasaninejad, E. Rostami, A.R. Moosavi-zare, M. Merajoddin, A. Arghoon, N. Pishahang, M. Shekouhy, E-Journal of Chemistry, 2009, 6, 390-396.

[36] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Catal. Commun., 2008, 9, 89-96.

 

[1] D.M. Brown, M.R.Wilson, W. MacNee, V. Stone, K. Donaldson, Toxicol. Appl. Pharm., 2001, 175, 191-199.

[2] K. Inoue, H. Takano, R. Yanagisawa, M. Sakurai, T. Ichinose, K. Sadakane, T. Yoshikawa, Respir. Res., 2005, 6, 106-113.

[3] G. Buzorius, A. Zelenyuk, F. Brechtel, D. Imre, Geophys Res Let., 2002, 29, 1974–1978.

[4] Zh. Chong-Shu, Ch-Ch. Chen, J-J. Cao, Ch-J. Tsai, Ch.C.-K. Chou, Sh-Ch. Liu, Atmos. Environ, 2010, 44, 2668-2673.

[5] S.S. Hang Ho, J. Zh. Yu, J. Chromatogr. A, 2004, 1059, 121–129.

[6] J. Dallüge, M. van Rijn, J. Beens, R.J.J. Vreuls, U.A.Th.Brinkman, J. Chromatogr. A, 2002, 965, 207-217.

[7] F. Adam, F. Bertoncini, N. Brodusch, E. Durand, D. Thiebaut, D. Espinat, M-C. Hennion, J. Chromatogr. A, 2007, 1148, 55–64.

[8] T. Hyölyläinen, M. Kallio, M. Shimmo, K. Saamio, K. Hartonen, M.L. Riekkola, in: Presentation at the First International Symposium on Two-Dimensional Gas Chromatography, Volendam, The Netherlands, 2003.

[9] C. Muhlen, C. Alcaraz Zini, E.B. Caramao, P.J. Marriott, J. Chromatogr. A., 2008, 1200, 34–42.

[10] M. Adahchour, M. Brandt, H.U. Baier, R.J.J. Vreuls, A.M. Batenburg, U.A.Th. Brinkman, J. Chromatogr. A., 2004, 1054, 57-65.

[11] J.F. Hamilton, P.J. Webb, A.C. Lewis, J.R. Hopkins, S. Smith, P. Davy, Atmos. Chem. Phys., 2004,4, 1279-1290.

[12] N. Ochiai, T. Ieda, K. Sasamoto, A. Fushimi, Sh. Hasegawa, K. Tanabe, Sh. Kobayashi, J. Chromatogr. A., 2007, 1150, 13–20.

[13] J. Leban, M. Baierl, J. Mies, V. Trentinaglia, S. Rath, K. Kronthaler, K. Wolf, A. Gotschlich, M.H.J. Seifert, J. Bioorg. Med. Chem. Lett.,2007, 17, 5858–5862.

[14] K. Bodzioch, A. Durand, R. Kaliszan, T. Bączek, Y. Vander Heyden, Talanta, 2010, 81, 1711-1718

[15] S. Riahi, E. Pourbasheer, M.R. Ganjali, P. Norouzi, J.Hazard.Mater.,2009, 166, 853-859.

[16] S.H. Woo, J. ChO, Y.S. Yun, H. Choi, Ch.S. Lee, D.S. Lee, J. Hazard. Mater.,2009, 161, 538–544

[17] N. Krämer, A.L. Boulesteix, G. Tutz, Chemom. Intell. Lab. Syst., 2008, 94, 6069.

[18] S. Haykin, Neural Networks, Prentice-Hall, New Jersey, 1999.

[19] R. Todeschini, V.Consonni, A.Mauri, M.Pavan, DRAGON-Software for the calculation of molecular descriptors. Version 3.0 for Windows, 2003.

[20] D.E. Goldberg, Genetic Algorithms in Search, Optimization and Machine Learning, Addison-Wesley–Longman, Reading, MA, USA, 2000.

[21] S. Riahi, E. Pourbasheer, R. Dinarvand, M.R. Ganjali, P. Norouzi, Exploring QSARs for antiviral activity of 4-alkylamino-6-(2-hydroxyethyl)-2- methylthiopyrimidines by support vector machine, Chem. Biol. Drug Des, 2008, 72, 205-216.

[22] J.A.d. Sousa, M.C. Hemmer, J. Casteiger, Prediction of H-1 NMR chemical shifts using neural networks, Anal. Chem., 2002, 74, 80-93.

[23] U. Depczynski, V.J. Frost, K. Molt, Genetic algorithms applied to the selection of factors in principal component regression, Anal. Chim. Acta., 2000, 420, 217-227.

[24] S. Wold, M. Sjostrom, L. Eriksson, PLS-regression: a basic tool of chemometrics, Chemom. Intell. Lab. Syst., 2001, 58, 109-130.

[25] B.M. Nicolai, K.I. Theron, J. Lammertyn, Chemom. Intell. Lab. Syst.,2007, 85, 243–252

[26] R. Rosipal, L.J. Trejo, J. Mach. Learning Res.,2001, 2, 97-123.

[27] J. Zupan, J. Gasteiger, Neural Network in Chemistry and Drug Design, Wiley–VCH, Weinheim, 1999.

[28] S. Kara, A.S. Güven, M. Okandan, F. Dirgenali, Comput. Biol. Med., 2006, 36, 473–483

[29] A. Yasri, D. Hartsough, J. Chem. Inf. Comput. Sci., 2001, 41, 1218-1227

[30] S. Kara, M. Okandan, Pattern Recognit,2007,40, 2967 – 2973

[31] M. Salvi, D. Dazzi, I. Pelistri, F. Neri, J.R. Wall, Ophthalmology, 2002, 109, 1703-1708.

[32] K.Kim, J.M.Lee, I.B. Lee, Chemom. Intell. Lab. Syst., 2005, 79, 22-30.

[33] J. Acevedo-Martınez, J.C. Escalona-Arranz, A. Villar-Rojas, F. Tellez-Palmero, R. Perez-Roses, L. Gonzalez, R. Carrasco-Velar, J. Chromatogr. A., 2006, 1102, 238-244.

[34] A. Afantitis, G. Melagraki, H. Sarimveis, P.A. Koutentis, J. Markopoulos, O. Igglessi-Markopoulou, Bioorg. Med. Chem.,  2006, 14, 6686-6694.

[35] A. Golbraikh, A. Tropsha, J. Mol. Graphics Modell, 2002, 20, 269-276.

[36] R. Todeschini, V. Consonni, Handbook of Molecular Descriptors, Wiley-VCH, Weinheim, Germany, 2000.