Silica sulfuric acid as an efficient and reusable heterogeneous catalyst for the synthesis of formamidines from the diaminomaleonitrile
محورهای موضوعی : Iranian Journal of Catalysis
Asieh Yahyazadeh
1
(Department of Chemistry, University of Guilan, P.O. Box 41335-1914, Rasht, I.R. Iran.)
Sara Hadesinea
2
(Department of Chemistry, University of Guilan, P.O. Box 41335-1914, Rasht, I.R. Iran.)
Mohammad Saeed Daneshmandi
3
(Department of Electrical and Computer Engineering, University of Tehran, Tehran, Iran.)
کلید واژه: Heterogeneous catalyst, Silica sulfuric acid, Imidate, Amidine, Diaminomaleonitrile,
چکیده مقاله :
Silica sulfuric acid as an efficient and reusable heterogeneous catalyst has been used for the preparation of amidines 2 from formimidate 1 by reaction with aromatic amines at room temperature in good to excellent yields. Imidate was prepared by treatment of equimolar quantities of triethyl orthoformate and diaminomaleonitrile in refluxing dioxane. All the compounds were characterized fully by spectroscopic techniques.
[1] M.J. Alves, B.L. Booth, A.P. Freitas, M.F. Proenca, J. Chem. Soc., Perkin Trans. 1 (1992) 913-917.
[2] B.L. Booth, A.M. Dias, M.F. Proenca, J. Chem. Soc., Perkin Trans. 1 (1992) 2119-2122.
[3] M.J. Alves, B.L. Booth, M.F. Proenca, J. Heterocycl. Chem. 31 (1994) 345-347.
[4] A. Yahyazadeh, B. Pourrostam, Bull. Korean. Chem. Soc. 24 (2003) 1723-1725.
[5] B.L. Booth, R.D. Coster, M.F. Proenca, Synthesis (1988) 389-392.
[6] R.L. Shriner, F.W. Neumann, Chem. Rev., 35 (1944) 351-425.
[7] (a) A. Yahyazadeh, Russ. J. Org. Chem. 39 (2003) 1649-1651; (b) M.J. Alves, B.L. Booth, M. A. Carvalho, R.G. Pritchard, M. F. Proenca, J. Heterocycl. Chem. (1997) 739-742.
[8] A. Yahyazadeh, B.L. Booth, Synth. Commun. 21 (2002) 3241-3246.
[9] A. Yahyazadeh, B.L. Booth, Synth. Commun. 31 (2001) 3225-3230.
[10] A. Al-Azmi, B.L. Booth, R.A. Carpenter, M.A. Carvalho, E. Marrelec, R.G. Pritchard, M.F. Proenca, J. Chem. Soc., Perkin Trans. 1 (2001) 2532-2539.
[11] B.L. Booth, I.M. Cabral, A.M. Dias, A.P. Freitas, A.M. Matos-Beja, M.F. Proenca, M. Ramos-Silva, J. Chem. Soc., Perkin Trans. 1 (2001) 1241-1248.
[12] J. Azizian, A. A. Mohammadi, E. Soleimani, A. R. Karimi, J. Hetrocyclc. Chem. 43 (2006) 187-190.
[13] F. Shirini, M.A. Zolifigol, K. Mohamadi, Bull. Korean, Chem. Soc. 25 (2004) 325-327.
[14] A. Ghorbani, H. Goudarziafshar, M. Hajjami, J. Soltani, J. Chin. Chem. Soc. 55 (2008) 119-123.
[15] M.M. Heravi, K. Bukhtiari, H.A. Oskooie, J. Mol. Catal.
A-Chem, 263 (2007) 279-281.
[16] H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A: Gen. 345 (2008) 128-133.
[17] A. Khazaei, A. Rostami, Z. Tanbakochian, Z. Zinati, J. Braz. Chem. Soc. 17 (2006) 206-209.
[18] D.W. Woodward, U.S. Patent 2 (1950) 534 331.
