W. K. Su, Z. Hong, W. G. Shan, X. X. Zhang
FULL PAPER
(
400 MHz, CDCl
3
): δ = 7.63 (dd, J = 2.8 Hz and 8.4 Hz, 1 H), 7.70
Supporting Information: (See footnote on the first page of this arti-
1
13
(d, J = 8.4 Hz, 1 H), 7.91 (d, J = 2.4 Hz, 1 H), 9.07 (s, 1 H) ppm. cle.) H NMR, C NMR, IR, and MS data of the products are
1
3
C NMR (100 MHz, CDCl
3
): δ = 120.45, 123.34, 132.25, 133.00,
included.
1
1
34.81, 134.89, 140.69 ppm. IR (KBr): ν˜ = 1580, 1492, 1428, 1249,
–1
214, 1034, 875 cm . MS (EI): m/z (%) = 219 (9), 217 (53), 215
Cl (215): calcd. C 39.09, H 1.87, N 26.06; found C
Acknowledgments
(100). C
7
H
4
2 4
N
3
9.14, H 1.83, N 26.11.
We are grateful to the National Basic Research Program
1
-(3,5-Dichlorophenyl)-1H-1,2,3,4-tetrazole (2i): Yield: 181 mg
(
No.2003CB114402), National Natural Science Foundation of
1
(84%) as colorless crystalline needles. M.p. 128 °C. H NMR
China (No.20476098), and National Natural Science Foundation
of Zhejiang Province (No.2002095) for financial support. We also
thank Shanghai Pesticide Research Institute for bioactivity deter-
mination.
(400 MHz, CDCl
3
): δ = 7.55 (t, J = 1.6 Hz, 1 H), 7.70 (t, J =
.6 Hz, 2 H), 9.07 (s, 1 H) ppm. 13C NMR (100 MHz, CDCl
): δ
119.66, 130.11, 135.01, 136.85, 140.35 ppm. IR (KBr): ν˜ = 1588,
1
=
1
2
2
3
–1
477, 1428, 1068, 1007, 854, 665 cm .MS (EI): m/z (%) = 219 (10),
17 (58), 215 (100). C Cl (215): calcd. C 39.09, H 1.87, N
7
H
4
2 4
N
6.06; found C 39.14, H 1.84, N 26.13.
[1] a) F. R. Benson, Chem. Rev. 1947, 41, 1–61; b) F. R. Benson in
Heterocylic Compounds (Ed.: R. C. Elderfield), John Wiley &
Sons, Inc., New York, 1967, p. 1.
[2] For reviews on the chemistry of tetrazoles, see: a) H. R. Meier,
H. Heimgartner, in Methoden der Organische Chemie (Houben-
Weyl) (Ed.: E. Schumann), Georg Thieme. Stuttgart, 1994, vol.
E8d, p. 664; b) R. N. Bulter in Comprehensive Heterocyclic
Chemistry (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Ox-
ford, 1984, vol. 5, p. 791.
1
4
-(2-Pyridine)-1H-1,2,3,4-tetrazole (2j): Yield: 131 mg (89%).
-Methyl-2-(1H-1,2,3,4-tetrazol-1-yl)pyridine (2k): Yield: 140 mg
1
(
(
1
(
1
1
87%) as pink crystalline needles. M.p. 130 °C.
400 MHz, CDCl
H), 8.37 (d, J = 5.2 Hz, 1 H), 9.52 (s, 1 H) ppm. 1 C NMR
100 MHz, CDCl ): δ = 21.02, 115.17, 126.05, 140.44, 147.18,
48.86, 152.09 ppm. IR (KBr): ν˜ = 1617, 1476, 1450, 1239, 1174,
H NMR
3
): δ = 2.50 (s, 3 H), 7.25–7.24 (m, 1 H), 7.89 (s,
3
3
[
3] a) E. Oliveri-Mandalà, B. Alagna, Gazz. Chim. Ital. 1910, 40,
II, 441–444; b) O. Dimroth, G. de Montmollin, Ber. Dtsch.
Chem. Ges. 1910, 43, 2904–2915; c) R. Stollé, F. Henke-Stark,
J. Parkt. Chem. 1930, 124, 261–300; d) F. G. Fallon, R. M.
Herbst, J. Org. Chem. 1957, 22, 933–936; e) Y. Satoh, N. Mar-
copulos, Tetrahedron Lett. 1995, 36, 1759–1762; f) T. Kamiya,
Y. Saito, US 3, 767, 667, 1973 [Chem. Abstr. 1971, 79, 5346 h];
g) A. K. Gupta, C. H. Oh, Tetrahedron Lett. 2004, 45, 4113–
–1
091, 995, 952, 838 cm . MS (EI): m/z (%) = 162 (45), 134 (100).
(161): calcd. C 52.16, H 4.38, N 43.46; found C 52.22, H
7 7 5
C H N
4
1
1
.42, N 43.41.
-Benzyl-1H-1,2,3,4-tetrazole (2l): Yield: 127 mg (79%).
-(4-Methoxybenzyl)-1H-1,2,3,4-tetrazole (2m): Yield: 143 mg
(75%).
4116; h) K. Nishiyama, M. Oba, A. Watanabe, Tetrahedron
(S)-1-(1-Phenylethyl)-1H-1,2,3,4-tetrazole (2n): Yield: 125 mg
1
987, 43, 693–700; i) T. Jin, S. Kamijo, Y. Yamamoto, Tetrahe-
1
7.4
(72%) as colorless crystals. M.p. 72–73 °C. [α]
D
= +23.04 (c =
dron Lett. 2004, 45, 9435–9437.
1
0
5
.1, methanol). H NMR (400 MHz, CDCl
.86 (m, 1 H), 7.42–7.29 (m, 5 H), 8.54 (s, 1 H) ppm. 13C NMR
): δ = 21.20, 59.18, 126.09, 126.51, 129.07,
29.22, 138.16, 141.61 ppm. IR (KBr): ν˜ = 1495, 1467, 1456, 1425,
3
): δ = 2.04 (m, 3 H), [4] a) M. J. Genin, D. A. Allwine, J. Med. Chem. 2000, 43, 953–
970; b) P. Ward, D. R. Armour, J. Med. Chem. 1995, 38, 4985–
992.
4
(100 MHz, CDCl
3
[
5] a) M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati, Tetra-
hedron Lett. 2001, 42, 3193–3195; b) J. J. Li, W. K. Su, J. D.
Lin, M. Chen, J. Li, Synth. Commun. 2005, 35, 1929–1937; c)
M. Curini, F. Epifano, F. Maltese, O. Rosati, Tetrahedron Lett.
1
1
–
1
383, 1258, 1208, 1163, 1112, 1097, 1069, 1051, 1027 cm . MS
(174): calcd. C 62.04,
H 5.79, N 32.17; found C 61.99, H 5.73, N 32.24.
9 10 4
(EI): m/z (%) = 117 (40), 105 (100). C H N
2
002, 43, 4895–4897.
[
6] S. Kobayashi, M. Sugiura, H. Kitagawa, Chem. Rev. 2002, 102,
1
-(2-Furylmethyl)-1H-1,2,3,4-tetrazole (2o): Yield: 107 mg (71%) as
1
2227–2302.
colorless crystalline needles. M.p. 85 °C. H NMR (400 MHz,
CDCl
7
[
7] Y. Chiang, A. J. Kresge, P. Salomaa, J. Am. Chem. Soc. 1974,
3
): δ = 5.64 (s, 2 H), 6.42–6.41 (m, 1 H), 6.56–6.55 (m, 1 H),
96, 4494–4499.
.46–7.45 (m, 1 H), 8.68 (s, 1 H) ppm. 13C NMR (100 MHz,
[
[
8] Y. Sun, M. W. Ding, Chin. J. Syn. Chem. 2004, 12, 126–130.
9] C. M. Grunert, P. Weinberger, J. Schweifer, C. Hampel, J. Mol.
Struct. 2005, 733, 41–52.
CDCl
3
): δ = 44.96, 111.24, 111.43, 142.69, 144.39, 145.79 ppm. IR
(KBr): ν˜ = 1506, 1476, 1430, 1354, 1260, 1165, 1154, 1104,
–1
1
016 cm . MS (EI): m/z (%) = 151 (100). C
6
H
6
N
4
O (150): calcd.
Received: January 4, 2006
C 47.99, H 4.03, N 37.32; found C 48.07, H 3.99, N 37.38.
Published Online: April 10, 2006
2726
www.eurjoc.org
© 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2006, 2723–2726