JOURNAL OF CHEMICAL RESEARCH 2012 51
9
R. Ballini, G. Bosica, M.L. Conforti, R. Maggi, A. Mazzacanni, P. Righi
and G. Sartori, Tetrahedron, 2001, 57, 1395.
3-Amino-1-(3,4,5-trimethoxyphenyl)-1H-benzo[f]chromene-2-carbonitrile
(14): H NMR (400 MHz, CDCl3): δ = 3.7 (s, 6H), 3.8 (s, 3H), 4.7
1
10 T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li and X.R. Song, Synlett, 2003, 2001.
11 T.S. Jin, J.C. Xiao, S.J. Wang and T.S. Li, Ultrason Sonochem., 2004, 11,
393.
12 D.Q. Shi, S. Zhang, Q.Y. Zhuang and X.S. Wang, Chin. J. Org. Chem.,
2003, 23, 1419.
13 B.S. Kumar, N. Srinivasulu, R.H. Udupi, B. Rajitha, Y.T. Reddy,
P.N. Reddy and P.S. Kumar, J. Heterocycl. Chem., 2006, 43, 1691.
14 M. Kidwai, S. Saxena, M.K. Rahman Khan and S.S. Thukral, Bioorg. Med.
Chem. Lett., 2005, 15, 4295.
(br, 2H), 5.2 (s, 1H), 6.4 (s, 2H), 7.2–7.3 (m, 1H), 7.4–7.5 (m, 2H),
7.7–7.8 (m, 1H), 7.8–7.9 (m, 2H) ppm; 13C NMR (100 MHz, CDCl3):
39.1, 44.9, 56.1, 60.8, 61.9, 104.2, 114.7, 116.6, 120.1, 123.8, 125.2,
127.3, 128.5, 129.8, 130.9, 131.3, 136.8, 140.2, 147.2, 153.5, 158.8
ppm; FT-IR (KBr, cm−1): 3454 (N–H), 3328 (N–H), 3062, 2936, 2189
(CN), 1659; Anal. Calcd for C23H20N2O4: C, 71.12; H, 5.19; N, 7.21.
Found: C, 71.15; H, 5.14; N, 7.18%.
15 A. Shaabani, R. Ghadari, S. Ghasemi, M. Pedarpour, A.H. Rezayan,
A. Sarvary and S. Weng Ng, J. Comb. Chem., 2009, 11, 956.
16 G. Shanthi and P.T. Perumal, Tetrahedron Lett., 2007, 48, 6785.
17 Y. Ren and C. Cai, Catal. Commun., 2008, 9, 1017.
18 M.M. Heravi, K. Bakhtiari, V. Zadsirjan, F.F. Bamoharram and O.M.
Heravi, Bioorg. Med. Chem. Lett., 2007, 17, 4262.
19 X.-S. Wang, G.-S. Yang and G. Zhao, Tetrahedron: Asymm., 2008, 19,
709.
Conclusion
In conclusion, we have developed a simple, efficient, and green
methodology for the synthesis of naphthopyranes using MNPs
under solvent-free conditions. The simple experimental proce-
dure, solvent-free reaction conditions, good yields, short time
reaction and utilisation of an efficient, easily recoverable and
reusable catalyst are the advantages of the present method.
20 D. Kumar, V.B. Reddy, B.G. Mishra, R.K. Rana, M.N. Nadagaouda and
R.S. Varma, Tetrahedron, 2007, 63, 3093.
21 M.P. Surpur, S. Kshirsagar and S.D. Samant, Tetrahedron Lett., 2009, 50,
719.
22 A. Solhy, A. Elmakssoudi, R. Tahir, M. Karkouri, M. Larzek, M. Bousmina
and M. Zahouily, Green Chem., 2010, 12, 2261.
We thank the Sistan and Baluchestan University Research
Council for partial support of this work.
23 A.H. Lu, E.L. Salabas and F. Schuth, Angew. Chem. Int. Ed. 2007, 46,
1222.
24 B. Hu, J. Pan, H.L. Yu, J.W. Liu and J.H. Xu, Process Biochem. 2009, 44,
1019.
Received 20 November 2011; accepted 9 January 2012
Paper 1100994 doi: 10.3184/174751912X13264750348839
Published online: 31 January 2012
25 S.C. Tsang, V. Caps, I. Paraskevas, D. Chadwick and D. Thompsett, Angew.
Chem. Int. Ed., 2004, 43, 5645.
26 M.Z. Kassaee, H. Masrouri and F. Movahedi, Appl. Cat. A: Gen., 2011,
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