RSC Advances
Page 12 of 15
DOI: 10.1039/C5RA14001C
5H), 7.69 (d, 4H), 7.97 (s, 1H), 12.25 (s, 1H, OH),
13.96(s, 1H, OH); 13C NMR (DMSOꢀd6): δ (ppm) 12.32,
14.76,32.64, 60.86,112.68, 119.66, 120.91, 122.33,
123.39, 124.81, 125.81, 126.80, 129.36, 136.72, 147.54,
153.62, 162.26; IR (KBr, cmꢀ1): 3456, 3061, 2924, 2884,
1709, 1622, 1603, 1551, 1497, 1456, 1398, 1319, 1260,
1182, 1151, 1096, 1030, 835, 785, 742, 689; m/z (%)= 548
(M+).
Chemical Synthesis (CEDEFMCS) for providing support
to this work.
Notes and references
Faculty of Chemistry, BuꢀAli Sina University, Hamedan 6517838683,
Iran
*Corresponding Author: Fax: +988138257407
Eꢀmail: zolfi@basu.ac.ir and mzolfigol@yahoo.com (M.A. Zolfigol).
† Electronic Supplementary Information (ESI) available: [details of any 65
supplementary information available should be included here]. See
DOI: 10.1039/b000000x/
60
5
4,4'ꢀ(Pyridinꢀ4ꢀylmethylene)bis(3ꢀmethylꢀ1ꢀphenylꢀ1Hꢀ
pyrazolꢀ5ꢀol) (Table 4, entry 9): Dark violet solid; m.p. 10
1
248ꢀ250, H NMR (400 MHz, DMSOꢀd6): δ (ppm) 2.29 (s,
1.
(a) Green Chemistry: Frontiers in Chemical Synthesis
and Processes, Oxford University Press, Oxford, 1998;
(b) M. Lancaster, Green Chemistry: An Introductory Text, 70
Royal Society of Chemistry, Cambridge, 2002; (c) J.
Clark and D. Macquarrie, Handbook of Green Chemistry
and Technology, Blackwell, Abingdon, 2002; (d) R. A.
Sheldon, Industrial Environmental Chemistry, Plenum,
6H), 5.29 (s, 1H, CH), 7.09 (t, 2H), 7.36 (t, 4H), 7.80 (s,
2H), 7.91 (d, 4H),8.82 (s, 2H), 12.33 (s, 1H, OH), 13.79
(s, 1H, OH); 13C NMR (DMSOꢀd6): δ (ppm) 15.92, 32.89,
111.65, 118.46, 121.16, 123.93, 129.06, 129.45, 139.64, 15
145.19, 149.45, 162.59; IR (KBr, cmꢀ1): 3352, 3087,
2983, 1651, 1634, 1593, 1481, 1319, 1163, 999, 813, 768;
m/z (%)= 435 (M+).
4ꢀ((3ꢀHydroxyꢀ5ꢀmethylꢀ1ꢀphenylꢀ1Hꢀpyrazolꢀ4ꢀyl)(3ꢀ
phenoxyphenyl)methyl)ꢀ3ꢀmethylꢀ1ꢀphenylꢀ1Hꢀpyrazolꢀ5ꢀ 20
ol (Table 4, entry 19): Cream solid; m.p. 194ꢀ195; 1H
NMR (400 MHz, DMSOꢀd6): δ (ppm) 2.31 (s, 6H), 4.99
(s, 1H, CH), 6.79 (d, 1H), 7.02 (m, 5H), 7.28 (m, 5H),
7.44 (t, 4H), 7.68 (d, 4H),12.50 (s, 1H, OH) 13.98 (s, 1H,
OH); 13C NMR (DMSOꢀd6): δ (ppm) 12.01, 33.32,116.28, 25
117.99, 118.86, 121.06, 122.88, 123.73, 126.15, 129.40,
130.13, 130.35, 137.63, 144.90, 146.74, 156.80, 156.85;
IR (KBr, cmꢀ1): 3434, 3070, 2923, 1598, 1578, 1498,
1439, 1371, 1253, 1224, 1161, 1019, 787, 752, 685; m/z
New York, 1992.
75
2.
(a) A. Solhy, A. Elmakssoudi, R. Tahir, M. Karkouri, M.
Larzek, M. Bousmina and M. Zahouily, Green Chem.,
2010, 12, 2261; (b) S. Otto and J. Engberts, J. Am. Chem.
Soc., 1999, 121, 6798; (c) S. Kobayashi and K. Manabe,
Acc. Chem. Res., 2002, 35, 209; (d) S. Shimizu, S. 80
Shirakawa, Y. Sasaki and C. Hirai, Angew. Chem., Int.
Ed., 2000, 39, 1256; (e) C. J. Li and C. M. Wei, Chem.
Commun., 2002, 268; (f) A. Solhy, A. Smahi, H. El
Badaoui, B. Elaabar, A. Amoukal, A. Tikad, S. Sebti and
D. J. Macquarrie, Tetrahedron Lett., 2003, 44, 4031; (g) 85
F. Bazi, H. El Badaoui, S. Tamani, S. Sokori, A. Solhy,
D. J. Macquarrie and S. Sebti, Appl. Catal. A., 2006, 301,
211; (h) A. K. Chakraborti, S. Rudrawar, K. B. Jadhav, G.
Kaur and S. V. Chankeshwara, Green Chem., 2007, 9,
1335; (i) G. L. Khatik, R. Kumar and A. K. Chakraborti, 90
Org. Lett., 2006, 8, 2432.
S. V. Chankeshwara and A. K. Chakraborti, Org. Lett.,
2006, 8, 3259.
R. Breslow, Acc. Chem. Res., 1991, 24, 159.
K. Manabe, S. Iimura, X. M. Sun and S. Kobayashi, J. 95
Am. Chem. Soc., 2002, 124, 11971.
(%)= 529 (M+).
30
4ꢀ(1ꢀ(5ꢀHydroxyꢀ3ꢀmethylꢀ1ꢀphenylꢀ1Hꢀpyrazolꢀ4ꢀyl)ꢀ2ꢀ
methylꢀ3ꢀphenylallyl)ꢀ3ꢀmethylꢀ1ꢀphenylꢀ1Hꢀpyrazolꢀ5ꢀol
(Table 4, entry 20): Pale yellow solid; m.p. 163ꢀ164; 1H
NMR (400 MHz, DMSOꢀd6): δ (ppm) 1.79 (s, 3H), 2.29(s,
6H), 4.33 (s, 1H, CH), 6.36 (s, 1H), 7.25 (m, 6H), 7.44 (t, 35
4H), 7.72 (d, 4H), 12.39 (s, 1H, OH), 13.89 (s, 1H, OH);
13C NMR (DMSOꢀd6): δ (ppm) 12.05, 17.89, 37.51, 84.28,
121.02, 124.74, 125.97, 126.50, 128.56, 129.22, 129.39,
137.46, 138.44, 146.89, 157.03; IR (KBr, cmꢀ1): 3435,
3058, 2921, 1602, 1579, 1500, 1379, 1266, 1188, 1023, 40
852, 793, 751, 688; m/z (%)= 476 (M+).
3.
4.
5.
6.
7.
8.
9.
T. W. Greene and P. G. M. Wuts, Protective Groups in
Organic Synthesis, John Wiley & Sons, USA, 1991.
Y. YuꢀDong, Lu. Xu, T. Etsuko and S. Norio, J. Fluorine
Chem., 2012, 143, 204.
G. K. S. Prakash, C. Panja, C. Do, T. Mathew and G. A.
Olah, Synlett., 2007, 2395.
(a) P. I. Dalko and L. Moisan, Angew. Chem., Int. Ed.,
2001, 40, 3726; (b) P. I. Dalko and L. Moisan, Angew.
Chem., Int. Ed., 2004, 43, 5138; (c) S. J. Connon, Synlett., 105
2009, 354; (d) S. J. Connon, Chem. Commun., 2008,
2499; (e) Y. Takemoto, Org. Biomol. Chem., 2005, 3,
4299; (f) P. R. Schreiner, Chem. Soc. Rev., 2003, 32, 289;
(g) A. G. Doyle and E. N. Jacobsen, Chem. Rev., 2007,
107, 5713; (h) B. List, Chem. Commun. 2006, 819; (i) M. 110
Marigo and K. A. Jrgensen, Chem. Commun., 2006, 2001;
(j) D. Enders, C. Grondal and M. R. M. Hüttl, Angew.
4ꢀ((4ꢀHydroxyꢀ3ꢀmethoxyphenyl)(5ꢀhydroxyꢀ3ꢀmethylꢀ1ꢀ
phenylꢀ1Hꢀpyrazolꢀ4ꢀyl)methyl)ꢀ3ꢀmethylꢀ1ꢀphenylꢀ1Hꢀ
pyrazolꢀ5ꢀol (Table 4, entry 24): Yellow solid; m.p. 205ꢀ
207; 1H NMR (400 MHz, DMSOꢀd6): δ (ppm) 2.30 (s, 45
6H), 3.66 (s, 3H), 4.84 (s, 1H, CH), 6.67 (t, 2H), 6.84 (s,
1H), 7.24 (t, 2H), 7.44 (t, 4H), 7.70 (d, 4H), 8.77 (s, 1H),
12.42 (s, 1H, OH), 14.01 (s, 1H, OH); 13C NMR (DMSOꢀ
d6): δ (ppm) 13.01, 33.31, 56.11, 112.38, 115.61, 120.08,
121.03, 126.01, 129.39, 133.73, 145.32, 146.61, 147.63, 50
154.33; IR (KBr, cmꢀ1): 3456, 3172, 2923, 1600, 1579,
1499, 1415, 1265, 1126, 1039, 782, 752, 692; m/z (%)=
481 (M+).
100
Acknowledgements
The authors gratefully acknowledge the BuꢀAli Sina 55
University Research Council and Center of Excellence in
Development of Environmentally Friendly Methods for
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