Paper
-(2,4-Dimethylphenyl)-1H-tetrazole (6g). White solid (91%
RSC Advances
1
8 (a) A. Burger, Prog. Drug. Res., 1991, 37, 287; (b) T. Schelenz
and W. Schafer, J. Fuel. Prakt Chem., 2000, 342, 9.
9 (a) V. V. Nilulin, T. V. Artamonova and G. I. Koldobskii,
Russ. J. Org. Chem., 2003, 39, 1525; (b) V. V. Nilulin, T.
V. Artamonova and G. I. Koldobskii, Russ. J. Org. Chem.,
1
yield); m.p. 133–135 uC. H NMR (DMSO-d , 250 MHz): d 6.87–
6
1
3
7
.67 (d, J = 6.0 Hz, 2H), 7.88 (s, 1H), 8.45 (s, 1H) ppm. C NMR
(
1
62.5 MHz, DMSO-d ): d 148.0, 131.6, 132.2, 128.1, 127.8,
6
2
1
21.5, 119.0, 20.1, 17.3 ppm. FT-IR (KBr) (nmax cm ): 2923,
2
1
2
005, 41, 444.
1
657, 1612, 1493, 1301, 1205, 1132, 823 cm . Anal. calcd for
:C, 68.56; H, 4.79; N, 26.65. Found: C, 68.13; H, 4.54;
N, 26.55.
-(4-Acetylphenyl)-1H-tetrazole (6h). Yellow solid (78%
1
0 (a) H. Torii, M. Nakadai, K. Ishihara, S. Saito and
H. Yamamoto, Angew. Chem., 2004, 116, 2017; (b)
Y. Yamamoto, N. Momiyama and H. Yamamoto, J. Am.
Chem. Soc., 2004, 126, 5962.
1 (a) S. Wittenberger, Org. Prep. Proced. Int., 1994, 26, 499; (b)
V. Aureggi and G. Sedelmeier, Angew. Chem., Int. Ed., 2007,
9 10 4
C H N
1
1
yield); m.p. 175–176 uC. H NMR (CDCl
3
, 250 MHz): d 2.76
1
(
s, 3 H), 7.78–7.97 (d, J = 8.7 Hz, 2 H), 8.12–8.31 (d, J = 8.7 Hz, 2
1
3
H), 9.32 (s, 1 H) ppm. C NMR (62.5 MHz, DMSO-d ): d 26.58,
6
4
6, 8440; (c) L. Bosch and J. Vilarrasa, Angew. Chem., Int.
1
22.32, 131.12, 136.00, 138.67, 142.22, 194.11 ppm. FT-IR (KBr)
2
1
Ed., 2007, 46, 3926; (d) D. P. Curran, S. Hadida and S.-
Y. Kim, Tetrahedron, 1999, 55, 8997; (e) K. Koguro, T. Oga,
S. Mitsui and O. Orita, Synthesis, 1998, 910; (f) S.
J. Wittenberger and B. G. Donner, J. Org. Chem., 1993, 58,
139; (g) B. E. Huff and M. A. Staszak, Tetrahedron Lett.,
993, 34, 8011; (h) J. V. Duncia, M. E. Pierce and J.
(nmax cm ): 3024, 1712, 1675, 1634, 1600, 1576, 1532, 1500,
2
1
1
5
243, 1056, 976 cm . Anal. Calcd for C
7.44; H, 4.28; N, 29.77. Found, C, 57.21; H, 4.00; N, 29.41.
-Methyl-6-(1H-tetrazol-1-yl)pyridine (6l). White solid (85%
9 8 4
H N O. Calcd, C,
2
4
1
1
yield); m.p. 106–107 uC. H NMR (250 MHz, CDCl
3
): d 2.90 (s, 3
H), 7.21–7.43 (m, 1 H), 7.84–8.02 (m, 2 H), 9.32 (s, 1 H) ppm.
B. Santella III, J. Org. Chem., 1991, 56, 2395–2400.
2 D. P. Green and J. E. A. J. Shuker, J. Comb. Chem., 2000, 2,
1
3
3
C NMR (62.5 MHz, CDCl ): d 123.4, 129.4, 130.2, 137.0, 155.3
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
1
ppm. FT-IR (KBr) (nmax cm ): 3025, 1632, 1587, 1555, 1511,
1
1
9.
3 A. Kumar, R. Narayanan and H. Shechter, J. Org. Chem.,
996, 61, 4462.
4 M. R. M. Bhoje and M. A. Gowd Pasha, J. Chem. Sci., 2011,
23, 75.
5 Y. S. Gyoung, J.-G. Shim and Y. Yamamoto, Tetrahedron
Lett., 2000, 41, 4193.
6 Z. Yizhong, R. Yiming and C. Chun, Helv. Chim. Acta, 2009,
2
1
497, 1254, 1065, 973 cm . Anal. Calcd for C H N . Calcd, C,
7 7 5
52.17; H, 4.38; N, 43.45. Found, C, 51.83; H, 4.01; N, 43.17.
1
1
Acknowledgements
We acknowledge Shiraz University for partial support of this
work.
9
2, 171.
7 M. L. Kantam, K. B. Shiva Kumar and C. Sridhar, Adv.
Synth. Catal., 2005, 347, 1212.
8 Z. P. Demko and K. B. Sharpless, J. Org. Chem., 2001, 66,
Notes and references
7
945.
1
2
3
H. Singh, A. S. Chawla, V. K. Kapoor, D. Paul and R.
K. Malhotra, Prog. Med. Chem., 1980, 17, 151.
9 S. Rostamizadeh, H. Ghaieni, R. Aryan and A. Amani, Chin.
Chem. Lett., 2009, 20, 1311.
0 M. L. Kantam, K. B. Shiva Kumar and K. J. Phani Raja, J.
Mol. Catal. A: Chem., 2006, 247, 186.
R. M. Demarinis, J. R. E. Hoover, G. L. Dunn, P. Actor, J.
V. Uri and J. A. Weisbach, J. Antibiot., 1975, 28, 463.
(a) T. Ichikawa, M. Yamada, M. Yamaguchi, T. Kitazaki,
Y. Matsushita, K. Higashikawa and K. Itoh, Chem. Pharm.
Bull., 2001, 49, 1110; (b) J. Matysiak, A. Niewiadomy,
E. Krajewska-Kulak and G. Macik-Niewiadomy, Farmaco,
1 S. Hajra, D. Sinha and M. Bhowmick, J. Org. Chem., 2007,
7
2, 1852.
2 M. L. Kantam, V. Balasubrahmanyam and K. B. Shiva
Kumar, Synth. Commun., 2006, 36, 1809.
3 L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu and G. Yin, Chem.
Commun., 2010, 46, 448.
4 T. Jin, F. Kitahara, S. Kamijo and Y. Yamamoto,
Tetrahedron Lett., 2008, 49, 2824.
5 G. Venkateshwarlu, A. Premalatha, K. C. Rajanna and P.
K. Saiprakash, Synth. Commun., 2009, 39, 4479.
6 M. Nasrollahzadeh, D. Habibi, Z. Shahkarami and Y. Bayat,
Tetrahedron, 2009, 65, 10715.
2
003, 58, 455; (c) R. S. Upadhyaya, S. Jain, N. Sinha,
N. Kishore, R. Chandra and S. K. Arora, Eur. J. Med. Chem.,
004, 39, 579.
2
4
5
A. Dlugosz, Pharmazie, 1995, 50, 180.
(a) I. Ueda, K. Ishii, K. Sinozaki and M. Htanaka, Chem.
Pharm. Bull., 1991, 39, 1430; (b) K. Terashima, T. Tanimura,
H. Shimamura, A. Kawase, K. Uenishi, Y. Tanaka,
I. Kamisaki, Y. Ishizuka and M. Sato, Chem. Pharm. Bull.,
1995, 43, 1042.
7 S. M. Agawane and J. M. Nagarkar, Catal. Sci. Technol.,
6
(a) R. R. Wexler, W. J. Greenlee, J. D. Irvin, M. R. Goldberg,
K. Prendergast, R. D. Smith and P. B. M. W.
M. Timmermans, J. Med. Chem., 1996, 39, 625; (b)
B. Schmidt and B. Schieffer, J. Med. Chem., 2003, 46,
2
012, 2, 1324.
8 M. Nasrollahzadeh, Y. Bayat, D. Habibi and S. Moshaee,
Tetrahedron Lett., 2009, 50, 4435.
9 J. Bonnamour and C. Bolm, Chem.–Eur. J., 2009, 15, 4543.
0 H. Eshghi, S.M. Seyedi and E. Rahimi Zarei, ISRN Organic
Chemistry, 2011, 1.
2
3
2261; (c) T. Tanaka, T. Okuda and Y. Yamamoto, Chem.
Pharm. Bull., 2004, 52, 830; (d) S. D. Lombaert, R. D. Ghai,
A. Y. Jeng, A. J. Trapani and R. L. Webb, Biochem. Biophys.
Res. Commun., 1994, 204, 407.
3
3
1 G. Qi and Y. Dai, Chin. Chem. Lett., 2010, 21, 1029.
2 (a) D. M. Zimmerman and R. A. Olofson, Tetrahedron Lett.,
7
L. B. Moskvin, A. V. Bulatov, G. L. Griogorjev and G.
I. Koldobkij, Flow Injection Anal., 2003, 20, 53.
1
969, 58, 5081; (b) F. G. Fallon and R. M. Herbst, J. Org.
4
370 | RSC Adv., 2013, 3, 4362–4371
This journal is ß The Royal Society of Chemistry 2013