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 , Seyed Mahdi Saadati ² , Mina Roshani ³ , Hasan Mohammadi ⁴ , Abbas Razavi ⁵ , Marjan Ramezani ⁶

1 - Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch, Mashhad 91735-413, Iran
2 - Young Researchers Club, Islamic Azad University, Mashhad Branch, Mashhad, Iran
3 - Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch, Mashhad 91735-413, Iran
4 - Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch, Mashhad 91735-413, Iran
5 - Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch, Mashhad 91735-413, Iran
6 - Department of Chemistry, Faculty of Basic Sciences, Islamic Azad University , Mashhad Branch, Mashhad 91735-413, Iran

تاریخ دریافت : 1388/01/06 تاریخ پذیرش : 1388/06/03 تاریخ انتشار : 1388/08/09

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.

منابع و مأخذ:

[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.