Study of an in situ carbocationic system formed from trityl chloride (Ph3CCl) as an efficient organocatalyst for the condensation of dimedone with arylaldehydes
الموضوعات : Iranian Journal of Catalysis
Abdolkarim Zare
1
(Department of Chemistry, Payame Noor University, Iran.)
Maria Merajoddin
2
(Department of Chemistry, Payame Noor University, Iran.)
Mohammad Ali Zolfigol
3
(Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6541835583, Iran.)
الکلمات المفتاحية: 5-dimethyl-1, Arylaldehyde, Dimedone (5, Trityl chloride (Ph3CCl), Trityl carbocation, Organocatalyst, 3-cyclohexanedione), 9-Aryl-1, 8-dioxo-octahydroxanthene,
ملخص المقالة :
Organocatalyst trityl chloride (Ph3CCl), by in situ formation of trityl carbocation with inherent instability, efficiently catalyzes the condensation of dimedone (5,5-dimethyl-1,3-cyclohexanedione) (2 equiv.) with arylaldehydes (1 equiv.) under solvent-free conditions to afford 9-aryl-1,8-dioxo-octahydroxanthenes in high to excellent yields and in relatively short reaction times. Formation of the carbocationic system is confirmed by studying IR, 1H NMR and UV spectra according to the literature. Moreover, a plausible mechanism based on the literature and observations is proposed for the reaction.
[1] E.N. Jacobsen, D.W.C. MacMillan, Proc. Natl. Acad. Sci. USA 107 (2010) 20618-20619.
[2] www.wikipedia.com.
[3] N. Iranpoor, H. Firouzabadi, N. Nowrouzi, D. Khalili, Tetrahedron 65 (2009) 3893-3899.
[4] J. Mondal, A. Modak, M. Nandi, H. Uyama, A. Bhaumik, RSC Adv. 2 (2012) 11306-11309.
[5] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, M. Khojasteh, Z. Asgari, V. Khakyzadeh, A. Khalafi-Nezhad, Catal. Commun. 20 (2012) 54-57.
[6] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, A. Parhami, A. Khalafi-Nezhad, Appl. Catal. A: Gen. 386 (2010) 179-187.
[7] A. Khalafi-Nezhad, A. Parhami, A. Zare, A.R. Moosavi Zare, A. Hasaninejad, F. Panahi, Synthesis (2008) 617-621.
[8] A. Khalafi-Nezhad, A. Parhami, A. Zare, A. Nasrollahi Shirazi, A.R. Moosavi Zare, A. Hasaninejad, Can. J. Chem. 86 (2008) 456-461.
[9] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, F. Abi, A. Zare, H. Kaveh, V. Khakyzadeh, M. Kazem-Rostami, A. Parhami, H. Torabi-Monfared, Tetrahedron 69 (2013) 212-218.
[10] A. Zare, M. Merajoddin, A. Hasaninejad, A.R. Moosavi-Zare, V. Khakyzadeh, C. R. Chim., 16 (2013) 380-384.
[11] B. Karami, S.J. Hoseini, K. Eskandari, A. Ghasemi, H. Nasrabadi, Catal. Sci. Technol. 2 (2012) 331-338.
[12] A. Khazaei, A.R. Moosavi-Zare, Z. Mohammadi, A. Zare, V. Khakyzadeh, G. Darvishi, RSC Adv. 3 (2013) 1323-1326.
[13] P.P. Salvi, A.M. Mandhare, A.S. Sartape, D.K. Pawar, S.H. Han, S.S. Kolekar, C. R. Chim. 14 (2011) 883-886.
[14] M.R. Poor Heravi, J. Iran. Chem. Soc. 6 (2009) 483-488.
[15] Z.-H. Zhang, Y.-H. Liu, Catal. Commun. 9 (2008) 1715-1719.
[16] G.H. Mahdavinia, M.A. Bigdeli, Y. Saeidi Hayeniaz, Chin. Chem. Lett. 20 (2009) 539-541.
[17] S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, G. Amiri, H. Sepehrian, Ultrason. Sonochem. 17 (2010) 306-309.
[18] J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem. 13 (1978) 67-71.
[19] Y.F. Qiao, T. Okazaki, T. Ando, K. Mizoue, K. Kondo, T. Eguchi, K. Kakinuma, J. Antibiot. 51 (1998) 282-287.
[20] G.W. Rewcastle, G.J. Atwell, L. Zhuang, B.C. Baguley, W.A. Denny, J. Med. Chem. 34 (1991) 217-222.
[21] J. Wichmann, K. Bleicher, E. Vieira, T. Woltering, F. Knoflach, V. Mutel, Farmaco 57 (2002) 989-992.
[22] R. J. Sarma, J.B. Baruah, Dyes Pigm. 64 (2005) 91-92.
[23] S.M. Menchen, S.C. Benson, J.Y.L. Lam, W. Zhen, D. Sun, B.B.S. Rosenblum, H. Khan, M. Taing, US Patent, US 6583168, 2003; Chem. Abstr. 139 (2003) 54287f.
[24] K. Tanaka, Solvent-Free Organic Synthesis, Wiley-VCH, GmbH and KgaA, Weinheim, Germany (2004).
[25] A. Zare, F. Abi, A.R. Moosavi-Zare, M.H. Beyzavi, M.A. Zolfigol, J. Mol. Liq. 178 (2013) 113-121.
[26] V. Polshettiwar, R.S. Varma, Tetrahedron Lett. 49 (2008) 2661-2664.
[27] A. Hasaninejad, A. Zare, M. Shekouhy, J. Ameri-Rad, Green Chem. 13 (2011) 958-964.
[28] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A: Gen. 400 (2011) 70-81.
[29] M. Oikawa, H. Yoshizaki, S. Kusumoto, Synlett (1998) 757-760.
