Silica-bonded n-propyltriethylene-tetramine as a recyclable solid base catalyst for the synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes

محورهای موضوعی : Iranian Journal of Catalysis

Marzieh Makvandi ¹ (Department of Chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.)
Fatemeh Abiar Dil ² (Department of Chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.)
Ameneh Malekzadeh ³ (Department of Chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.)
Mojtaba Baghernejad ⁴ (Young Researchers and Elite Club, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran.)
Khodabakhsh Niknam ⁵ (Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran.)

تاریخ دریافت : 1392/06/11 تاریخ پذیرش : 1392/09/18 تاریخ انتشار : 1392/09/10

کلید واژه: Synthesis, Catalyst, Silica-bonded n-propyltriethylene-tetramine, Chromenes, Solid bases,

چکیده مقاله :

Silica-bonded n-propyltriethylene-tetramine (SBNPTT) was found as an efficient solid base for the synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Chromene derivatives were obtained via the three-component condensation reaction of aromatic aldehydes, malononitrile, and dimedone at 80 oC under solvent-free conditions. The heterogeneous solid base showed much the same efficiency when used in consecutive reaction runs.

منابع و مأخذ:

[1]    D. Choudhary, S. Paul, R. Gupta, J.H. Clark, Green Chem., 8 (2006) 479-482.
[2]    K. Niknam, D. Saberi, Appl. Catal. A Gen., 366 (2009) 220-225.
[3]    F. Rohandeh, D. Saberi, K. Niknam, Iran. J. Catal., 1 (2011) 71-78.
[4]    S. Tayebi, K. Niknam, Iran. J. Catal., 2 (2012) 69-74.
[5]    K. Niknam, A. Jamali, Chin. J. Catal., 33 (2012) 1840-1849.
[6]    K. Niknam, M. Sadeghi Habibabad, A. Deris, N. Aeinjamshid, Monatsh. Chem., 144 (2013) 987-992.
[7]    K. Niknam, N. Borazjani, R. Rashidian, A. Jamali, Chin. J. Catal., 34 (2013) 2245-2254
[8]    K. Niknam, M. Sadeghi Habibabad, A. Deris, F. Panahi, M. R. Hormozi Nezhad, J. Iran. Chem. Soc., 10 (2013) 527-534.
[9]    K. Niknam, A. Deris, F. Panahi, Chin. J. Catal., 34 (2013) 718-722.
[10]    E. C. Witte, P. Neubert, A. Roesch, Ger. Offen., DE3427985 (1986).
[11]    E. A. Hafez, M. H. Elnagdi, A. A. Elagamey, F. A. El-Taweel, Heterocycles, 26 (1987) 903-907.
[12]    J. Kuthan, Adv. Heterocycl. Chem., 34 (1983) 145-303.
[13]    S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc. Chem. Commun., (1988) 1202-1204.
[14]     J. Zamocka, E. Misikova, J. Durinda, Pharmazie, 46 (1991) 610-615.
[15]    J. L. Wang, D. Liu, Z. J. Zhang, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. USA 97 (2000) 7124-7129.
[16]     A. M. M. El-Saghier, M. B. Naili, B. K. Rammash, N. A. Saleh, K. M. Kreddan, Arkivoc, xvi (2007) 83-91.
[17]     R. R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett., 17 (2007) 6459-6462.
[18]     M. Kidwai, S. Saxena, M. K. R. Khan, S. S. Thukral, Bioorg. Med. Chem. Lett., 15 (2005) 4295-4298.
[19]     M. Suarez, E. Salfran, Y. Verdecia, E. Ochoa, L. Alba, N. Martin, R. Martinez, M. Quinteiro, C. Seoane, H. Novoa, N. Blaton, O. M. Peeters, C. De Ranter, Tetrahedron, 58 (2002) 953-960.
[20]     K. Singh, J. Singh, H. Singh, Tetrahedron, 52 (1996) 14273-14280.
[21]     A. A. Hassanien, M. A. Zahrran, M. S. A. El-Gaby, M. M. Ghorab, J. Indian Chem. Soc., 76 (1999) 350-354.
[22]     J. F. Zhou, S. J. Tu, Y. Gao, M. Ji, Chin. J. Org. Chem., 21 (2001) 742-745.
[23]     S. J. Tu, H. Jiang, Q. Y. Zhuang, C. B. Miu, D. Q. Shi, X. S. Wang, Y. Gao, Chin. J. Org. Chem., 23 (2003) 488-490.
[24]     T. S. Jin, A. Q. Wang, X. Wang, J. S. Zhang, T. S. Li, Synlett, (2004) 871-873.
[25]     D. Q. Shi, S. Zhang, Q. Y. Zhuang, S. J. Tu, H. W. Hu, Chin. J. Org. Chem., 23 (2003) 877-879.
[26]     X. S. Wang, D. Q. Shi, S. J. Tu, C. S. Yao, Synth. Commun., 33 (2003) 119-126.
[27]     L. M. Wang, J. H. Shao, H. Tian, Y. H. Wang, B. Liu, J. Fluorine Chem., 127 (2006) 97-100.
[28]     S. Balalaie, M. Bararjanian, A. M. Amani, B. Movassagh, Synlett, (2006) 263-266.
[29]     S. Gao, C. H. Tsai, C. Tseng, C. F. Yao, Tetrahedron, 64 (2008) 9143-9149.
[30]     A. Hasaninejad, M. Shekouhy, N. Golzar, A. Zare, M. M. Doroodmand, Appl. Catal. A Gen., 402 (2011) 11-22.
[31]     Y. Sarrafi, E. Mehrabi, A. Vahid, M. Tajbakhsh, Chin. J. Catal., 33 (2012) 1486-1494.
[32]     J. M. Khurana, B. Nand, P. Saluja, Tetrahedron, 66 (2010) 5637-5641.