Document Type : Original Research Article

Authors

1 Department of Chemistry, Faculty of Sciences, University of Birjand

2 Sharif University of Technology

Abstract

A novel Schiff-base ligand (L: 2-[(4-chloro-2-oxo-2H-chromen-3-ylmethylene)-amino] propionic acid) was prepared from the reaction of 4-chloro3-formylcoumarin and alanine amino acid. Copper (II) complex was synthesized from the reaction of the ligand with Cu (OAc)2. H2O in ethanol. The ligand and its metal complex were characterized by elemental analysis (CHN), ICP, thermal analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), 1HNMR, and 13C NMR techniques. The complex was found to be an efficient catalyst and reusable in the selective oxidation of sulfides to the corresponding sulfoxides without the formation of any sulfone using the green oxidant, H2O2, at room temperature and under solvent-free conditions.

Graphical Abstract

Synthesis, characterization and selective oxidation using a new copper (II) Schiff base complex derived from Alanine and 4-chloro3- formyl coumarin

Keywords

Main Subjects

[1] O. Güngör, P. Gürkan, J. Mol. Struct., 2014, 1074, 62-70.
[2]  N. Nishal,  D. Singh, A. Kumar, V. Tanwar, S. Singh,  R. Srivastava, P.A. Singh, J. Org. Semicond., 2014, 2, 15-20.
[3] H. Shekaari , A. Kazempour, M. Khoshalhan, Phys. Chem.   Phys., 2015, 17, 2179-2191.
[4]   S. Yamada, Coord. Chem. Rev., 1966, 1, 415-437.
[5]   L. Sacconi L, Coord. Chem. Rev., 1966, 1, 126-132.

[6] M. Nath, P.K. Saini, Dalton Trans., 2011, 40, 7077-7121.

[7] Z. Cimerman, S. Miljanić N. Galić, Croat.Chem. Acta., 2000, 73, 81-95.

[8] N. Sarì, P. Gürkan, Transition met. chem., 2003, 28, 687-693.
[9] K. Shivakuma, M. Shashidhar, P. Vithal Reddy, M.B. Halli, J.Coord.Chem., 2008, 61, 2274-2287.
[10] N.S. Geweely, Arch. microbiol., 2009, 191, 687-695.
[11] R. Kaushal, S. Thakur, Chem. Eng. Trans., 2013, 32, 1801-1806.
[12] S.B. Desai, P.  Desai, K. Desai, Heterocycl. commun., 2001, 7, 83-90.

[13] Gh. Grivani, G. Bruno, H. Amiri Rudbari,  A. Dehno Khalaji, P. Pourteimouri, Inorg. Chem. Commun., 2012, 18, 15-20.

[14] O. Pouralimardan, A.C. Chamayou, C. Janiak, H. Hosseini-Monfared, Inorg  Chim Acta., 2007, 360, 1599-1608.

[15]   X.B. Lu, X.J. Feng, R.  He, Appl. Catal. A., 2002, 234, 25-33.
[16] R. Das, D. Chakraborty, Tetrahedron Lett., 2010, 51, 6255-6258.
[17] J.N. Moorthy, K. Senapati, K.N.  Parida, J. Org. Chem., 2010, 75, 8416-8421.
[18] B. Karimi, M. Ghoreishi-Nezhad, J.H.  Clark, Org. Lett., 2005, 7, 625-628.
[19] M. Bagherzadeh, R. Latifi, L. Tahsini, M. Amini, Catal. Commun., 2008, 10, 196-200.

[20] V. Conte, F. Fabbianesi, B. Floris, P. Galloni, D. Sordi, I.W. Arends, M. Bonchio, D. Rehder, D. Bogdal, Pure. Appl. Chem., 2009, 81, 1265-1277.

[21] J. Li, J. Dong, H.A. Cui, Transition Met Chem., 2012, 37, 175-182.
[22] C.H. Oh, V.R. Reddy, Tetrahedron lett., 2004, 45, 8545-8548.
[23] C. Chowdhury, N.G. Kundu, Tetrahedron lett., 1996, 37, 7323-7324.
[24] S. Caron, R.W. Dugger, S.G. Ruggeri, J.A. Ragan, D.H.B. Ripin, Chem. Rev., 2006, 106, 2943-2989.

[25] P. Le Maux, G. Simonneaux, Chem. Commun., 2011, 47, 6957-6959.

[26] V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammdpoor-Baltork, H. Kargar, M. Araghi, Appl. Catal., A.  2009, 353, 61-67.

[27] M. Jaccob, P. Comba, M. Maurer, P. Vadivelu, P. Venuvanalingam, Dalton Trans., 2011, 40, 11276-11281.

[28] J.M. Khurana, B.  Nand, Can. J. Chem., 2010, 88, 906-909.
[29] A. Hasaninejad, Gh. Chehardoli, M.A. Zolfigol, A. Abdoli, Phosphorus, Sulfur, and Silicon and the Related Elements., 2011, 186, 271-280.

[30] A. Rostami, J.A. Akradi, Tetrahedron Lett., 2010, 51, 3501-3503.

[31] S.R. Moorty, V. Sundaramurthy N.V.  Subba Rao, Indian J. Chem., 1973, 11, 854-856. 

[32] Ö. Güngör, P. Gürkan, J. Mol. Struct., 2014, 1074, 62-70.

[33] X. Wang, G. WU, F. Wang, W. Wei, Y. Sun, Chin J Catal., 2011, 32, 1812-1821.

[34] L.J. Bellamy, 3rd ed.; Wiley & Sons: New Yourk, 1975, 231-262.

[35] H. Keypour, M. Shayesteh, D. Nematollahi, L. Valencia, H.A. Rudbari, J. Coord. Chem., 2010, 63, 4165-4176.

[36] S.H. Wang, B.S. Mandimutsira, R. Todd, B. Ramdhanie, J.P. Fox, D.P. Goldberg, J. Am. Chem. Soc., 2004, 126, 18-19.
[37] M. Al-Hashimi, G. Roy, A.C. Sullivan, J.R.H. Wilson, Tetrahedron Lett., 2005, 46, 4365-4398.
[38] B. Zhang,    M.D. Zhou,   M. Cokoja,   J. Mink,   S.L. Zang, F.E.  Kühn, RSC Adv., 2012, 2, 8416-8420.
[39] H.B. Jeon, K.T. Kim, S.H. Kim, Tetrahedron Lett., 2014, 55, 3905-3908.
 
[40] T.H. Chen, Z. Yuan, A. Carver, R. Zhang, Appl. Catal., A, 2014, 478, 275-282.
[42] Z.D. Li , R. Ma, L.N. He, Chin. Chem. Lett., 2015, 26, 539-542.
[43] Q. Zeng, W. Wengc, X. Xue, Inorg. Chim. Acta., 2012, 388, 11-15.