Sulfuric acid immobilized on silica: A versatile and reusable heterogeneous catalyst for the synthesis of phenanthrimidazole derivatives
محورهای موضوعی : Journal of the Iranian Chemical Research
Hossein Behmadi
1
(Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch,
Mashhad 91735-413, Iran)
Seyed Mahdi Saadati
2
(Young Researchers Club, Islamic Azad University, Mashhad Branch, Mashhad, Iran)
Mina Roshani
3
(Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch,
Mashhad 91735-413, Iran)
Hasan Mohammadi
4
(Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch,
Mashhad 91735-413, Iran)
Abbas Razavi
5
(Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch,
Mashhad 91735-413, Iran)
Marjan Ramezani
6
(Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch,
Mashhad 91735-413, Iran)
کلید واژه: 1H-phenanthro[9, 10]imidazol-2-yl, Phenanthraquinone, Triethyl orthoesters, Sulfuric acid,
چکیده مقاله :
A new, convenient, efficient, and cost-effective one-pot synthesis of 1Hphenanthro[9,10]imidazol-2-yl from phenanthraquinone and aldehydes, using sulfuric acidimmobilized on silica as catalyst is described. The present methodology offers severaladvantages such as excellent yields, simple procedure, shorter reaction times, the use ofinexpensive reagents, easy recovery and eco-friendly. In addition to these, 2-alkylphenanthrimidazole is obtained from triethyl orthoesters in good yields.
[1] L. Nagarapu, S. Apuri, S. Kantevari, J. Mol. Catal. A: Chem. 266 (2007) 104-108.
[2] F.C. Krebs, H. Spanggaard, J. Org. Chem. 67 (2002) 7185-7192.
[3] A.R. Karimi, Z. Alimohammadi, J. Azizian, A.A. Mohammadi, M.R. Mohammadizadeh, Catal.
Commun. 7 (2006) 728-732.
[4] J.N. Sangshetti, N.D. Kokare, S.A. Kotharkar, D.B. Shinde, Chin. Chem. Lett. 19 (2008) 762-766.
[5] A.Y. Usyatinsky, Y.L. Khmelnitsky, Tetrahedron Lett. 41 (2000) 5031-5034.
[6] S.E. Wolkenberg, D.D. Wisnoski, W.H. Leister, Y. Wang, Z. Zhao, C.W. Lindsley, Org. Lett. 6
(2004) 1453-1456.
[7] S.A. Siddiquo, U.C. Narkhede, S.S. Palimkar, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Tetrahedron 61
(2005) 3539-3546.
[8] E.A. Steck, A.R. Day, J. Am. Chem. Soc. 65 (1943) 452-456.
[9] B. Radziszewski, Chem. Ber. 15 (1882) 1493-1496.
[10] F.R. Japp, H.H. Robinson, Chem. Ber. 15 (1882) 1268-1270.
[11] B. Li, C.K.F. Chiu, R.F. Hank, J. Murry, J. Roth, H. Tobiassen, Org. Proc. Res. Dev. 6 (2002) 682.
[12] P.F. Zhang, Z.C. Chen, Synthesis (2001) 2075-2077.
[13] F.R. Japp, F.W. Streatfield, J. Chem. Soc. 41 (1882) 146-156.
[14] S. Sarshar, D. Siev, A.M.M. Mjalli, Tetrahedron Lett. 37 (1996) 835-838.
[15] F.J. Liu, J. Chem, J. Zhao, Y. Zhao, L. Li, H. Zhang, Synthesis (2003) 2661-2666.
[16] D.E. Frantz, L. Morency, A. Soheilli, J.A. Murry, E.J.J. Grabowski, R.O. Tillyer, Org. Lett. 6 (2004)
843-846.
[17] H. Wienmann, M. Harre, K. Koeing, E. Mertin, U. Tilstam, Tetrahedron Lett. 43 (2002) 593-595.
[18] S. Tamagaki, R.J. Card, D.C. Neckers, J. Am. Chem. Soc. 100 (1978) 6635-6639.
[19] I. Mohammadpoor-Baltork, V. Mirkhani, M. Moghadam, Sh. Tangestaninejad, M.A. Zolfigol, M.
Abdollahi-Alibeik, A.R. Khosropour, H. Kargar, S.F. Hojati, Catal. Commun. 9 (2008) 894-901.
[20] (a) M.A. Zolfigol, A. Bamoniri, Synlett (2002) 1621-1624; (b) M.A. Zolfigol, Tetrahedron 57 (2001)
9509-9511; (c) M.A. Zolfigol, F. Shirini, A. Ghorbani Choghamarani, I. Mohammadpoor-Baltork,
Green Chem. 4 (2002) 562-564.
[21] F. Shirini, M.A. Zolfigol, K. Mohammadi, Bull. Korean Chem. Soc. 25 (2004) 325-327.
[22] B. Mukhopadhyay, Tetrahedron Lett. 47 (2006) 4337-4341.
[23] V.K. Rajput, B. Roy, B. Mukhopadhyay, Tetrahedron Lett. 47 (2006) 6987-6991.
H. Behmadi et al. / J. Iran. Chem. Res. 2 (2009) 183-187
187
[24] M.M. Heravi, N. Ramezanian, M.M. Sadeghi, M. Ghassemzadeh, Phosphorus Sulfur Silicon Relat.
Elem. 179 (2004) 1469-1742.
[25] B. Roy, B. Mukhopadhyay, Tatrahedron Lett. 48 (2007) 3783.
[26] M.M. Heravi, H.R. Khademalfoghara, M.M. Sadeghi, Sh. Khaleghi, M. Ghassemzadeh, Phosphorus
Sulfur Silicon Relat. Elem. 181 (2006) 377-380.
[27] H. Sato, K. Nagai, H. Yoshioka, Y. Nagaoka, Appl. Catal. A 180 (1999) 359-366.
[28] H. Behmadi, M. Roshani, S.M. Saadati, Chin. Chem. Lett. 20 (2009) 5-8.
