Page 11 of 12
RSC Advances
RSC Advances
DOI: 10.1039/C6RA03023H
ARTICLE
246, 1094, 1002, 772, 675, 576. H NMR (400 MHz, DMSO, 8.20 (m, 4H), 2.64 (s, 3H); C NMR (100 MHz, DMSO, ppm)
ppm) = 8.00ꢀ8.09 (m, 1H), 8.01ꢀ8.04 (m, 1H), 7.63 ꢀ7.69 (m, 2H). 197.9, 156.1, 138.6, 129.6, 129.5, 127.5, 27.3.
1
13
1
δ =
δ
2
2
2
1
-(1H-tetrazol-5-yl) phenol (Table 2, Entry 2): white solid, m.p. 5-(4-Methoxyphenyl)-1H-tetrazole (Table 2, Entry 11): white
ꢀ
1
ꢀ1
25 ºC (Lit. [12]: 224ꢀ225), FTꢀIR (KBr): νmax/cm : 3253, 3059, solid, m.p. 230ꢀ232 ºC (Lit. [14]: 230), FTꢀIR (KBr): νmax/cm :
933, 2709, 2566, 2359, 1610, 1545, 1475, 1393, 1358, 1294, 1230, 3432, 3155, 3081, 2926, 2855, 2726, 2623, 2555, 2474, 1616, 1503,
1
115, 1068, 946, 808, 742, 680, 541. H NMR (400 MHz, DMSO, 1450, 1404, 1302, 1262, 1174, 1119, 1052, 1022, 939, 834, 804,
1
ppm)
6
δ
= 8.00ꢀ8.02 (m, 1H), 7.40ꢀ7.44 (m, 1H), 7.08ꢀ7.11 (m, 1H), 747, 696, 608, 519. H NMR (400 MHz, DMSO, ppm)
δ
= 7.97ꢀ8.01
1
3
13
.99ꢀ7.03 (m, 1H), 11.10 (br, 1H), 15.73 (br, 1H); C NMR (100 (m, 2H), 7.16ꢀ7.19 (m, 2H); 3.85 (s, 3H); C NMR (100 MHz,
MHz, DMSO, ppm) = 155.7, 152, 133.1, 129.5, 120.2, 116.7, DMSO, ppm) = 161.9, 155.1, 129.1, 116.7, 115.3, 55.9.
δ
δ
1
10.9.
Acknowledgements
5
-(4-Nitrophenyl)-1H-tetrazole (Table 2, Entry 3): Yellow solid,
ꢀ
1
m.p. 216ꢀ218 ºC (Lit. [21]: 218ꢀ219), FTꢀIR (KBr): νmax/cm : 3508,
3
1
The authors are deeply gratitude Ilam University, Ilam, Iran for
financial support of this research project.
101, 2967, 2919, 2854, 2755, 2547, 1646, 1608, 1521, 1439, 1346,
1
156, 1101, 1024, 951, 854, 721, 696, 494. H NMR (400 MHz,
DMSO, ppm)
Hz, 2H).
δ = 8.41ꢀ8.43 (d, J= 8.8 Hz, 2H), 8.29ꢀ8.31 (d, J= 8.8
References
5
-(3-Nitrophenyl)-1H-tetrazole (Table 2, Entry 4): White solid,
1. Sarvary, A. Maleki, A. Mol Divers, 2015, 19, 189.
m.p. 149ꢀ152 ºC (Lit. [12]: 154ꢀ156), FTꢀIR (KBr): νmax/cm : 3852, 2. F. Abrishami, M. Ebrahimikia, F. Rafiee, appl.
ꢀ
1
3
1
=
308, 3085, 2975, 2894, 2822, 2752, 1621, 1524, 1348, 1243, 1156,
Organometal. Chem. 2015, 22, 730.
3. M. A. E. A. Ali. Ali. ElꢀRemaily, S. K. Mohamed,
Tetrahedron, 2014, 70, 270.
1
076, 1011, 912, 819, 727, 453. H NMR (400 MHz, DMSO, ppm)
8.85 (s, 1H), 8.43ꢀ8.50 (m, 2H), 7.90ꢀ7.94 (m, 1H).
δ
4
. A. Palazzi, S. Stagni, S. Selva, M. Monari, J. Organomet.
Chem. 2003, 669, 135.
5
-(4-Chlorophenyl)-1H-tetrazole (Table 2, Entry 5): white solid,
ꢀ
1
m.p. 257ꢀ260 ºC (Lit. [21]: 261ꢀ262), FTꢀIR (KBr): νmax/cm : 3436, 5. H. Sharghi, S. Ebrahimpour moghaddam, M.
M
2
6
769, 2634, 1908, 1607, 1484, 1432, 1265, 1155, 1091, 988, 831,
Doroodmand, J. Organomet. Chem. 2013, 738, 41.
. Z. P. Demko, K. B. Sharpless, J. Org. Chem. 2001, 66
945.
. D. R. Patil, Y. B. Wagh, P. G. Ingole, K. Singh, D. S. Dalal,
New. J. Chem. 2013, 37, 3261.
. J. Bonnamour, C. Bolm, Chem. Eur. J. 2009, 15, 4543.
. G. Venkateshwarlu, A. Premalatha, K. C. Rajanna, P. K.
Saiprakash, Synth. Commun. 2009, 39, 4479.
1
6
7
,
96, 505. H NMR (400 MHz, DMSO, ppm)
δ = 8.05ꢀ8.07 (d, J= 8.4
7
Hz, 2H), 7.69ꢀ7.71 (d, J= 8.4 Hz, 2H).
5
-(4-Bromophenyl)-1H-tetrazole (Table 2, Entry 6): white solid,
ꢀ
1
8
9
m.p. 267 ºC (Lit. [21]: 264ꢀ264), FTꢀIR (KBr): νmax/cm : 3443,
2
8
2
4
956, 2923, 2861, 2766, 2627, 1601, 1423, 1317, 1152, 1055, 998,
1
42, 734, 562. H NMR (400 MHz, DMSO, ppm)
H), 7.81ꢀ7.84 (m, 2H).
δ = 7.97ꢀ8.00 (m,
1
1
1
1
0. P. Mani, A. K. Singh, S. K. Awasthi, Tetrahedron Lett.
014, 55, 1879.
1. M. Parveen, F. Ahmad, A. M. Malla, S. Azaz, New J. Chem.
015, 39, 2028.
2. M. Abdollahi Alibeika, A. Moaddeli, New J. Chem. 2014,
, 2116.
3. L. Bosch, J. Vilarrasa, J. Angew. Chem. 2007, 46, 3926.
2
-(1H-tetrazol-5-yl)benzonitrile (Table 2, Entry 7): white
solid, m.p. 191.193 ºC (Lit. [21]: 190ꢀ191), FT.IR (KBr):
νmax/cm : 3476, 3150, 3090, 3018, 2923, 2859, 2724, 2624,
2
1
2
ꢀ
1
566, 2485, 2232, 1620, 1566, 1494, 1431, 1364, 1275, 1153,
3
9
1
067, 1028, 847, 749, 695, 552. H NMR (400 MHz, DMSO,
1
3
ppm)
δ
= 8.21ꢀ8.24 (m, 2H), 8.09ꢀ8.12 (m, 2H); CNMR (100 14. A. KhalafiꢀNezhad, S. Mohammadi, RSC Adv. 2013,
= 155.7, 133.8, 129.2, 128.1, 118.6,
4362.
15. V. Polshettiwar, R. S. Varma, Tetrahedron, 2010, 66, 1091.
6. R. Mohammadi, M. Z. Kassaee, J. Mol. Catal. A: Chem.
013, 380, 152.
-Phenyl-1H-tetrazole (Table 2, Entry 8): White solid, m.p. 224ꢀ
3,
MHz, DMSO, ppm)
1
δ
13.9.
1
2
5
2
1
ꢀ
1
17. F. Dehghani, A. R. Sardarian, M. Esmaeilpour, J.
Organomet. Chem. 2013, 743, 87.
26 ºC (Lit. [21]: 214ꢀ216), FTꢀIR (KBr): νmax/cm : 3436, 2920,
1
610, 1559, 1474, 1405, 1252, 1159, 1051, 987, 784, 689, 492. H
1
8. A. GhorbaniꢀChoghamarani, G. Azadi, RSC Adv., 2015,
752.
5,
NMR (400 MHz, DMSO, ppm)
2
δ = 7.59ꢀ7.65 (m, 3H), 8.04ꢀ8.08 (m,
9
H).
1
9. A. GhorbaniꢀChoghamarani, B. Ghasemi, Z. Safari, G.
Azadi, Catal. Commun. 2015, 60, 70.
20. A. GhorbaniꢀChoghamarani, F. Nikpour, F. Ghorbani and F.
5
-(4-Isopropylphenyl)-1H-tetrazole (Table 2, Entry 9): white solid,
ꢀ
1
m.p. 189 ºC (Lit. [24]: 191ꢀ192), FTꢀIR (KBr): νmax/cm : 3436,
2
1
Havasi, RSC Adv. 2015,
5, 33212.
924, 2858, 1717, 1634, 1457, 1359, 1299, 1162, 835, 747, 541. H
2
2
1. N. Razavi, B. Akhlaghinia, RSC Adv. 2015, 5, 87769.
2. M. HosseiniꢀSarvari, S. NajafvandꢀDerikvandi, C. R.
Chimie, 2014, 17, 1007.
3. M. L. Kantam, K. B. Shiva Kumar, K. J. Phani Raja, J. Mol.
Catal. A: Chem. 2006, 247, 186.
24. P. Sivaguru, P. Theerthagiri, A. Lalitha, Tetrahedron Lett.
NMR (400 MHz, DMSO, ppm)
.48ꢀ7.51 (d, J= 8.4 Hz, 2H), 2.94ꢀ3.04 (m, 1H), 1.25ꢀ1.26 (d, J= 6.8
Hz, 6H).
δ = 7.96ꢀ7.98 (d, J= 8.4 Hz, 2H),
7
2
1
-(4-(1H-tetrazol-5-yl)phenyl)ethanone (Table 2, Entry 10): white
ꢀ
1
solid, m.p. 175ꢀ178 ºC (Lit. [25]: 181),, FT.IR (KBr): νmax/cm
:
2
015, 56, 2203.
3
1
8
432, 3144, 3079, 3011, 2969, 2921, 2858, 2719, 2625, 2472, 1680,
2
5. D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, L. Vaccar,
570, 1431, 1365, 1271, 1156, 1120, 1081, 1058, 997, 982, 961,
1
J. Org. Chem. 2004, 69, 2896.
41, 752, 704, 589, 491. H NMR (400 MHz, DMSO, ppm)
δ =8.14ꢀ
This journal is © The Royal Society of Chemistry 2013
J. Name., 2013, 00, 1-3 | 11