Ammonium chloride catalyzed microwave-assisted synthesis of tetrahydrobenzo[b]pyrans
الموضوعات : Iranian Journal of CatalysisVijay Pagore 1 , Sunil Tekale 2 , Vivekanand Jadhav 3 , Rajendra Pawar 4
1 - Department of Chemistry, Deogiri College, Station Road, Aurangabad (MS) India 431 005.
2 - Department of Chemistry, Shri Muktanand College, Gangapur (MS) India 431 109.
3 - Department of Chemistry, Shri Muktanand College, Gangapur (MS) India 431 109.
4 - Department of Chemistry, Deogiri College, Station Road, Aurangabad (MS) India 431 005.
الکلمات المفتاحية: MW irradiation, Tetrahydrobenzo[b]pyrans, Ammonium chloride,
ملخص المقالة :
In the present work, we have developed a mild, efficient, and environmentally benign method for the synthesis of tetrahydrobenzo[b]pyran derivatives via a three-component cyclocondensation of aldehydes, malononitrile and dimedone utilizing ammonium chloride as a simple, easily available and cost effective catalyst under microwave irradiation. This method has several attracting features such as simple experimental set up, easy work-up procedure, high conversions and short reaction times affording the products in moderate to excellent yield.
[1] E. Sheikhhosseini, D. Ghazanfari, V. Nezamabadi, Iran. J. Catal. 3 (2013) 197-201.
[2] S.S. Pourpanah, S.M. Habibi-Khorassani, M. Shahraki, Chin. J. Catal. 3 (2015) 757-763.
[3] T.S. Jin, A.Q. Wang, F. Shi, L.S. Han, L.B. Liu, T. S. Li, Arkivoc xiv (2006) 78-86.
[4] M.G. Dekamin, M. Eslami, A. Maleki, Tetrahedron 69 (2013) 1074-1085.
[5] S. Balalaie, M. Sheikh-Ahmadi, M. Bararjanian, Catal. Commun. 8 (2007) 1724-1728.
[6] M. Saha, A.K. Pal, Adv. Nanopart. 1 (2012) 61-70.
[7] J. Azizian, F. Teimouri, M.R. Mohammadizadeh, Catal. Commun. 8 (2007) 1117-1121.
[8] M. Dabiri, M. Bahramnejad, M. Baghbanzadeh, Tetrahedron 65 (2009) 9443-9447.
[9] A. Shaabani, A. Bazgir, F. Teimouri, Tetrahedron Lett. 44 (2003) 857-859.
[10] F. Teimouri, S. HadiKhezri, Z. Miri, B. Eftekhari-Sis, J. Azizian, J. Sci. 19 (2009) 103-108.
[11] S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron 64 (2008) 9143-9149.
[12] M. Kazemzad, A.A. Yuzbashi, S. Balalaie, M. Bararjanian, Synth. React. Inorg. Met. Org. Chem. 41 (2011) 1182-1187.
[13] A. Patra, T.J. Mahapatra, J. Chem. Res.34 (2010) 689-693.
[14] S. Balalaie, M. Bararjanian, A.M. Amani, B. Movassagh, Synlett (2006) 263-266.
[15] D. Fang, H.B. Zhang, Z.L. Liu, J. Heterocycl. Chem. 47 (2010) 63-67.
[16] Mobinikhaledi, M.A.B. Fard, Acta Chim. Slov. 57 (2010) 931-935.
[17] X.Z. Lian, Y. Huang, Y.Q. Li, W.J. Zheng, Monatsh. Chem. 139 (2008) 129-131.
[18] N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35 (2014) 391-395.