9
22
A. N. Chermahini, A. Teimouri, F. Momenbeik, A. Zarei, Z. Dalirnasab, A. Ghaedi, and M. Roosta Vol 47
3
14–216 C; H NMR (DMSO-d , 400 MHz): 7.7–8.1 (5H, m);
C NMR (DMSO-d , 100 MHz); 164, 134, 133, 132, 131, 129,
6
-(1H-tetrazole-5-yl)benzonitrile (8b). White solid; mp ¼
[7] Burg, D.; Hameetman, L.; Filippov, D. V.; van der Marel,
G. A.; Mulder, G. J. Bioorg Med Chem Lett 2002, 12, 1579.
ꢀ
1
2
6
13
[
8] Hayashi, R.; Jin, X.; Cook, G. R. Bioorg Med Chem Lett
007, 17, 6864.
[9] Duncia, J. V.; Pierce, M. E.; Santella, J. B., III. J Org
2
1
2
15 ppm; MS (70 eV) m/z: 171, 143, 102, 62; IR (KBr) t: 3113,
ꢁ
1
981, 2780, 2442, 2237, 1476, 870, 780 cm ; R
t
¼ 8.0 min.
Chem 1991, 56, 2395.
2
-(1H-tetrazole-5-yl)benzonitrile (9b). White solid; mp ¼
ꢀ
1
[10] Kumar,A.;Narayanan,R.;Shechter,H.JOrgChem1996,61,4462.
[11] Curran, D. P.; Hadida, S.; Kim, S.-Y. Tetrahedron 1999, 55, 8997.
2
7
08–210 C; H NMR (DMSO-d , 400 MHz): 7.6 (t, J ¼ 6.8 Hz, 1H),
6
13
.7 (t, J ¼ 6.8 Hz, 1H), 7.8 (m, 2H) ppm; C NMR (DMSO-d , 100
6
[
[
12] Hajra, S.; Sinha, D.; Bhowmick, M. J Org Chem 2007, 72, 1852.
13] Kantam, M. L.; Balasubrahmanyam, V.; Shiva Kumar, K.
MHz); 166, 140, 136, 133, 132, 128, 126, 118, ppm; MS (70 eV) m/z:
1
1
71, 143, 129, 115, 88, 76, 62, 57; IR (KBr) t: 3096, 2531, 2110, 2023,
B. Synth Commun 2006, 36, 1809.
14] Amantini, D.; Beleggia, R.; Fringuelli, F.; Pizzo, F.; Vac-
ꢁ
1
632, 1436, 845 cm ; R
t
¼ 12 min.
[
4
-(1H-tetrazole-5-yl)benzaldehyde (10b). White solid; mp ¼
coro, L. J Org Chem 2004, 69, 2896.
ꢀ
1
1
2
d
80–182 C; H NMR (DMSO-d , 400 MHz): 7.9 (d, J ¼ 7.2 Hz,
6
[15] Demko, Z. P.; Sharpless, K. B. J Org Chem 2001, 66, 7945.
1
3
H), 8.0 (d, J ¼ 7.2 Hz, 2H), 9.1 (s, 1H) ppm; C NMR (DMSO-
[
16] Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. J
6
, 100 MHz); 188, 156, 138, 131, 129, 128 ppm; MS (70 eV) m/
Am Chem Soc 2002, 124, 12210.
z: 174, 146, 130, 116, 102, 90, 57, 43; IR (KBr) t: 3015, 2924,
[17] Balogh, M.; Laszlo, P. Organic Chemistry Using Clays;
Springer: Berlin, 1993.
ꢁ
1
2
854, 2713, 2612, 1667, 1440, 776 cm ; R ¼ 6.4 min.
t
4
48–250 C; H NMR (DMSO-d
-(1H-tetrazole-5-yl) benzoic acid (11b). White solid; mp ¼
[18] Motokura, K.; Fujita, N.; Mori, K.; Mizugaki, T.; Ebitani,
K.; Kaneda, K. J Am Chem Soc 2005, 127, 9674.
[19] Choudary, B. M.; Bhaskar, V.; Kantam, M. L.; Rao, K. K.;
Raghavan, K. V. Green Chem 2000, 2, 67.
ꢀ
1
13
6
, 400 MHz): 7–8 (m, 4H) ppm; C
2
NMR (DMSO-d
6
, 100 MHz); 188, 166, 138, 131, 129, 128 ppm; MS
(
3
70 eV) m/z: 190, 174, 146, 130, 116, 102, 90, 75, 57; (KBr) t: 3600–
ꢁ
1
[
20] Ballini, R.; Bosica, G.; Maggi, R.; Ricciutelli, M.; Righi,
000 (br), 2500, 1760, 1500, 1480, 780 cm ; R ¼ 6.9 min.
t
P.; Sartori, G.; Sartorio, R. Green Chem 2001, 3, 178.
[21] Jankovic, L.; Komadel, P. J Catal 2003, 218, 227.
[22] Laszlo, P. Pure Appl Chem 1990, 62, 2027.
4-(1H-tetrazole-5-yl)phenyl acetate (12b). White solid; mp
212–214 C; H NMR (DMSO-d
ꢀ
1
¼
6
, 400 MHz): 7.9 (d, J ¼ 7.4 Hz,
1
3
2
H), 7.7 (d, J ¼ 7.4 Hz, 2H), 2.59 (s, 3H); ppm; C NMR (DMSO-
[
23] Heravi, M. M.; Derikvand, F.; Ranjbar, L. A.; Oskooie, H.
d , 100 MHz); 170, 164, 152, 131, 128, 124, 22 ppm; MS (70 eV)
6
A. Heteroatom Chem 2008, 19, 215.
m/z: 204, 189, 173, 160, 145, 130, 102, 90; (KBr) t: 3097, 2925,
ꢁ
1
[24] Shaikh, N. S.; Bhor, S. S.; Gajare, A. S.; Deshpande, V. H.;
Wakharkar, R. D. Tetrahedron Lett 2004, 45, 5395.
2
865, 2700, 2625, 1678, 1580, 1269, 843 cm ; R
General procedure for preparation of tetrazoles under
ultrasonic irradiation. In a round bottom flask, benzonitrile
0.2 g, 2 mmol,), sodium azide (0.4 g, 6mmol), and DMF or
t
¼ 12.84 min.
[
25] (a) Yadav, J. S.; Subba Reddy, B. V.; Satheesh, G. Tetrahe-
dron Lett 2004, 45, 3673; (b) Sabu, K. R.; Sukumar, R.; Lalithambika,
M. Bull Chem Soc Jpn 1993, 66, 3535.
(
water (20 mL) were charged. The flask was suspended into the
ultrasonic bath at the reaction temperature (333 K). Then, 50
mg of catalyst (montmorillonite K-10 or kaolin) was added
and the reaction time measured. The flask was suspended at
the center of the bath. The progress of the reaction was moni-
tored by TLC. After that the reaction was cooled to room tem-
perature, and product was recovered as mentioned.
[
26] Dintzner, M. R.; Little, A. J.; Pacilli, M.; Pileggi, D. J.;
Osner, Z. R.; Lyons, T. W. Tetrahedron Lett 2007, 48, 1577.
27] Leite, L.; Stonkus, V.; Edolfa, K.; Ilieva, L.; Plyasova, L.;
[
Zaikovskii, V. Appl Catal A 2006, 311, 86.
[28] Hirano, M.; Monobe, H.; Yakabe, S.; Morimoto, T. J Chem Res
(S) 1998, 662.
[29] Dabbagh, H. A.; Chermahini, A. N.; Banibairami, S. Tetra-
hedron Lett 2006, 47, 3929.
[
30] Dabbagh, H. A.; Chermahini, A. N.; Teimouri, A. Heteroa-
tom Chem 2006, 17, 416.
31] Chermahini, A. N.; Esfahani, M. N.; Dalirnasab, Z.; Dab-
bagh, H. A.; Teimouri, A. J Mol Struct (Theochem) 2007, 820, 7.
32] Dabbagh, H. A.; Chermahini, A. N.; Teimouri, A. Dyes
Pigments 2007, 73, 239.
33] Dabbagh, H. A.; Chermahini, A. N.; Teimouri, A. Appl
Acknowledgment. Support from Yasouj University (YU) is
gratefully acknowledged. The authors thank the faculty members
in the Instrumental Analysis Center of Isfahan Payame Noor Uni-
versity for the measurements of mass spectra.
[
[
[
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