Microwave-assisted one-pot synthesis of 1-amidoalkyl 2-naphthols and dibenzo [a,j] xanthenes using phosphorus pentoxide on solid supports

محورهای موضوعی : Iranian Journal of Catalysis

Amin Zarei ¹ ( Department of Science, Fasa Branch, Islamic Azad University, Post Box No 364, Fasa, 7461713591, Fars, Iran )

تاریخ دریافت : 1390/09/20 تاریخ پذیرش : 1390/11/19 تاریخ انتشار : 1390/10/11

کلید واژه: 1-Amidoalkyl 2-naphthols, Dibenzoxanthenes, Phosphorus pentoxide, Solid supports, Microwave irradiation,

چکیده مقاله :

A convenient, efficient and practical procedure for the synthesis of 1-amidoalkyl 2-naphthols is described by condensation of aromatic aldehydes with amides and 2-naphthol in the presence of P2O5/SiO2 as an efficient catalyst. Moreover, in the present of this catalyst, the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes is studied by condensation of aldehydes with 2-naphthol. Using solvent-free conditions, non-toxic and inexpensive materials, simple and clean work-up, short reaction times and high yields of the products are the advantages of this method.

منابع و مأخذ:

[1] P. E. Eaton, G. R. Carlson, J. T. Lee, J. Org. Chem. 38 (1973) 4071-4073.

[2] B. Kaboudin, Y. Abedi, Org. Prep. Proced. Int. 41 (2009) 229-236.

[3] N. Yonezawa, T. Hino, K. Matsuda, T. Matsuk, D. Narushima, M. Kobayashi, T. Ikeda, J. Org. Chem. 65 (2000) 941-944.

[4] S. R. Akhtar, J. V. Crivello, J. L. Lee, J. Org. Chem. 55 (1990) 4222-4225.

[5] H. Eshghi, Z. Gordi, Phosphorus Sulfur Silicon Relat. Elem. 180 (2005) 619-623.

[6] H. Eshghi, A. Hassankhani, Synth. Commun. 36 (2006) 2211-2216.

[7] F. Tamaddon, M. Khoobi, E. Keshavarz, Tetrahedron Lett. 48 (2007) 3643-3646.

[8] A. Hasaninejad, A. Zare, H. Sharghi, M. Shekouhya, ARKIVOC xi (2008) 64-74.

[9] A. Zarei, A. R. Hajipour, L. Khazdooz, Tetrahedron Lett. 49 (2008) 6715-6719.

[10] A. Zarei, A. R. Hajipour, L. Khazdooz, B. B. F. Mirjalili, S. Zahmatkesh, J. Mol. Catal. A: Chem. 301 (2009) 39-46.

[11] A. Khazaei, M. N. Soltani Rad, M. Kiani Borazjani, S. Saednia, M. Kiani Borazjani, M. Golbaghi, S. Behrouz, Synth. Commun. 41 (2011) 1544-1553.

[12] A. Zarei, A. R. Hajipour, L. Khazdooz, Synth. Commun. 41 (2011) 1772-1785.

[13] Y. F. Wang, T. Izawa, S. Kobayashi, M. Ohno, J. Am. Chem. Soc. 104 (1982) 6465-6466.

[14] S. Knapp, Chem. Rev. 95 (1995) 1859-1876.

[15] D. Seebach, J. L. Matthews, J. Chem. Soc. Chem. Commun. (1997) 2015-2022.

[16] E. Uaristi, In Enantioselective Synthesis of β-Amino Acids; John Wiley & Sons, New York, 1997.

[17] T, Dingermann, D. Steinhilber, G. Folkers, In Molecular Biology in Medicinal Chemistry; Wiley-VCH, 2004.

[18] A. Y. Shen, C. T. Tsai, C. L Chen, Eur. J. Med. Chem. 34 (1999) 877-882.

[19] M. M. Khodaei, A. R. Khosropour, H. Moghanian, Synlett (2006) 916-920.

[20] S. Kantevari, S. V. N. Vuppalapati, L. Nagarapu, Catal. Commun. 8 (2007) 1857-1862.

[21] N. P. Selvam, P. T. Perumal, Tetrahedron Lett. 47 (2006) 7481-7483.

[22] B. Das, K. Laxminarayana, B. Ravikanth, R. Rao, J. Mol. Catal. A: Chem. 261 (2007) 180-183.

[23] H. R. Shaterian, H. Yarahmadi, M. Ghashang, Bioorg. Med. Chem. Lett. 18 (2008) 788-792.

[24] W. K. Su, W. Y. Tang, J. J. Li, J. Chem. Res. (2008) 123-128.

[25] L. Nagarapu, M. Baseeruddin, S. Apuri, S. Kantevari, Catal. Commun. 8 (2007) 1729-1734.

[26] S. B. Patil, P. R. Singh, M. P. Surpur, S. D. Samant, Ultrasonics Sonochem. 14 (2007) 515-518.

[27] W. Q. Jiang, L. T. An, J. P. Zou, Chin. J. Chem. 26 (2008) 1697-1701.

[28] S. B. Patil, P. R. Singh, M. P. Surpur, S. D. Samant, Synth. Commun. 37 (2007) 1659-1664.

[29] G. Srihari, M. Nagaraju, M.M. Murthy, Helv. Chim. Acta 90 (2007) 1497-1504.

[30] H. R. Shaterian, H. Yarahmadi, M. Ghashang, Tetrahedron 64 (2008) 1263-1269.

[31] A. R. Hajipour, Y. Ghayeb, N. Sheikhan, A. Ruoho, Tetrahedron Lett. 50 (2009) 5649-5651.

[32] M. Lei, L. Ma, L. Hu, Tetrahedron Lett. 50 (2009) 6393-6397.

[33] N. N. Greenwood, A. Earnshaw, Chemistry of the Elememts; Pergamon press, 1985.

[34] J. H. Clark, Catalysis of Organic Reactions by Supported Inorganic Reagents, VCH, New York, 1994.

[35] A. M. El-Brashy, M. E. Metwally, F. A. El-Sepai, Farmaco 59 (2004) 809-817.

[36] J. M. Jamison, K. Krabill, A. Hatwalkar, Cell Bio. Int. Rep. 14 (1990) 1075-1084.

[37] K. Chibale, M. Visser, D. V. Schalkwyk, P. J. Smith, A. Saravanamuthu, A. H. Fairlamb, Tetrahedron 59 (2003) 2289-2296.

[38] B. B. Bhowmik, P. Ganguly, Spectrochimi Acta 61 (2005) 1997-2003.

[39] C. G. Knight, T. Stephens, Biochem. J. 258 (1989) 683-687.

[40] A. Ahmad, T. A. King, B. H. Cha, J. Lee, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.

[41] A. R. Khosropour, M. M. Khodaei, H. Moghannian, Synlett (2005) 955-958.

[42] A. Saini, S. Kumar, J. S. Sandhu, Synlett (2006) 1928-1932. 

[43] S. Ko, C. F. Yao, Tetrahedron Lett. 47 (2006) 8827-8829.

[44] M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dyes Pigments 76 (2008) 836-839.

[45] H. R. Shaterian, M. Ghashang, A. Hassankhani, Dyes Pigments 76 (2008) 564-568.

[46] M. A. Pasha, V. P. Jayashankara, Bioorg. Med. Chem. Lett. 17 (2007) 621-623.

[47] B. Das, B. Ravikanth, R. Ramu, K. Laxminarayana, B. V. Rao, J. Mol. Catal. A: Chem. 255 (2006) 74-77.

[48] B. Rajitha, B. S. Kumar, Y. T. Reddy, P. N. Reddy, N. Sreenivasulu, Tetrahedron Lett. 46 (2005) 8691-8693.

[49] M. M. Amini, M. Seyyedhamzeh, A. Bazigir, Appl. Cata. A: Gen. 323 (2007) 242-245.

[50] M. M. Heravi, K. Bakhtiari, Z. Daroogheha, F. F. Bamoharram, J. Mol. Catal. A: Chem. 273 (2007) 99-101.

[51] W. Su, D. Yang, C. Jin, B. Zhang, Tetrahedron Lett. 49 (2008) 3391-3394.

[52] M. Dabiri, M. Baghbanzadeh, M. Shakourinikcheh, E. Arzroomchilar, Bioorg. Med. Chem. Lett. 18 (2008) 436-438.

[53] B. B. F. Mirjalili, A. H. Bamoniri, A. Akbari, Tetrahedron Lett. 49 (2008) 6454-6456.

[54] A. Sharifi, S. Abaee, A. Tavakkoli, M. Mirzaei, A. Zolfagharei, Synth. Commun. 38 (2008) 2958-2966.

[55] S. Kantevari, M. V. Chary, A. P. R. Das, S. V. N. Vuppalapati, N. Lingaiah, Catal. Commun. 9 (2008) 1575-1578.

[56] K. Pratibha, V. Yathindranath, S. M. S. Chauhan, Synth. Commun. 38 (2008) 637-648.

[57] K. Gong, D. Fang, H. L. Wang, X. L. Zhou, Z. L. Liu, Dyes Pigments 80 (2009) 30-33.

[58] A. R. Hajipour, Y. Ghayeb, N. Sheikhan, A. E. Ruoho, Synlett (2010) 741-744.

[59] L. Khazdooz, A. Zarei, A. R. Hajipour, N. Sheikhan, Iranian J. Catal. 1 (2011) 1-9.