Synthesis of Tetrazoles in Aqueous Micelles
6-Methoxy-2-(1H-tetrazol-5-yl)benzo[d]thiazole (13q): Off-white so-
Acknowledgments
lid; m.p. 241–243 °C. FTIR (KBr): ν = 3415, 3136, 2169, 1616,
˜
1569, 1386, 1135, 979, 578 cm–1. 1H NMR (500 MHz, [D6]DMSO):
δ = 8.04 (d, J = 8.9 Hz, 1 H), 7.84 (d, J = 2.5 Hz, 1 H), 7.24 (dd,
J = 9.0, 2.6 Hz, 1 H), 3.89 (s, 3 H) ppm. 13C NMR (125 MHz, [D6]-
DMSO): δ = 158.95, 152.77, 150.84, 147.59, 137.03, 124.50, 117.51,
105.34, 56.30 ppm. HRMS (ESI): calcd. for C9H8N5OS [M + H]+
234.0444; found 234.0445.
The authors thank the National Nature Science Foundation of
China (NSFC) (grant number 30870625) and the Analysis and
Testing Centre of Nanjing University of Science and Technology
for NMR and MS measurements.
2-(1H-Tetrazol-5-yl)benzo[d]thiazol-6-ol (13r): Yellowish solid; m.p.
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Ͼ290 °C. FTIR (KBr): ν = 3447, 3162, 2169, 1731, 1573, 1384,
˜
1135, 979 cm–1. 1H NMR (500 MHz, [D6]DMSO): δ = 9.75 (s, 1
H), 7.78 (d, J = 8.7 Hz, 1 H), 7.34 (d, J = 2.4 Hz, 1 H), 6.93 (dd,
J = 8.7, 2.4 Hz, 1 H) ppm. 13C NMR (125 MHz, [D6]DMSO): δ =
157.70, 156.73, 155.99, 147.56, 136.27, 123.70, 116.11, 107.08 ppm.
HRMS (ESI): calcd. for C8H6N5OS [M + H]+ 220.0288; found
220.0291.
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2-(1H-Tetrazol-5-yl)benzo[d]oxazole (13s): White solid; m.p. 221–
224 °C. FTIR (KBr): ν = 3207, 2659, 1911, 1675, 1450, 1037, 748
˜
cm–1. 1H NMR (500 MHz, [D6]DMSO): δ = 7.83 (dd, J = 7.5,
3.8 Hz, 2 H), 7.46 (td, J = 15.3, 7.0 Hz, 2 H) ppm. 13C NMR
(125 MHz, [D6]DMSO): δ = 154.64, 151.34, 150.37, 140.87, 126.86,
125.76, 120.64, 111.74 ppm. HRMS (ESI): calcd. for C8H6N5O [M
+ H]+ 188.0567; found 188.0562.
5-Chloro-2-(1H-tetrazol-5-yl)benzo[d]oxazole (13t): White solid;
m.p. 217–219 °C. FTIR (KBr): ν = 3454, 3161, 2383, 2169, 1913,
˜
1637, 1386, 1155, 1043, 578 cm–1. 1H NMR (500 MHz, [D6]-
DMSO): δ = 8.09 (d, J = 2.0 Hz, 1 H), 7.99 (d, J = 8.8 Hz, 1 H),
7.62 (dd, J = 8.7, 2.1 Hz, 1 H) ppm. 13C NMR (125 MHz, [D6]-
DMSO): δ = 153.68, 149.35, 149.26, 142.09, 130.27, 127.60, 120.73,
113.38 ppm. HRMS (ESI): calcd. for C8H5ClN5O [M + H]+
222.0177; found 222.0176.
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2-(1H-Tetrazol-5-yl)-1H-benzo[d]imidazole (13u): Off-white solid;
m.p. Ͼ290 °C. FTIR (KBr): ν = 3442, 2632, 1735, 1409, 1124, 916,
˜
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752 cm–1. 1H NMR (500 MHz, [D6]DMSO): δ = 7.72 (dd, J = 6.1, [10] a) B. H. Lipshutz, D. W. Chung, B. Rich, Org. Lett. 2008, 10,
3.2 Hz, 2 H), 7.43 (dd, J = 6.1, 3.1 Hz, 2 H) ppm. 13C NMR
(125 MHz, [D6]DMSO): δ = 157.09, 143.32, 138.85, 125.94, 118.18
ppm. HRMS (ESI): calcd. for C8H7N6 [M + H]+ 187.0727; found
187.0727.
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6-Methoxy-2-(1H-tetrazol-5-yl)-1H-benzo[d]imidazole (13v): Off-
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white solid; m.p. Ͼ290 °C. FTIR (KBr): ν = 3444, 3126, 2169,
˜
1633, 1386, 1128, 949, 578 cm–1. 1H NMR (500 MHz, [D6]DMSO):
δ = 7.62 (d, J = 8.9 Hz, 1 H), 7.13 (d, J = 2.2 Hz, 1 H), 7.05 (dd,
J = 8.9, 2.4 Hz, 1 H) ppm. 13C NMR (125 MHz, [D6]DMSO): δ =
159.80, 152.33, 142.77, 140.46, 138.06, 119.58, 117.68, 99.96, 58.74
ppm. HRMS (ESI): calcd. for C9H6N5O2 [M + H]+ 217.0832;
found 217.0836.
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2-(1H-Tetrazol-5-yl)-4H-benzo[d][1,3]oxazin-4-one (13w): Off-white
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solid; m.p. Ͼ290 °C. FTIR (KBr): ν = 3417, 3118, 1677, 1606,
˜
2610.
1
1386, 1272, 754, 551 cm–1. H NMR (500 MHz, [D6]DMSO): δ =
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12.56 (s, 1 H), 8.76 (dd, J = 8.4, 0.8 Hz, 1 H), 8.16–8.06 (m, 1 H),
7.76–7.63 (m, 1 H), 7.3–7.18 (m, 1 H) ppm. 13C NMR (125 MHz,
[D6]DMSO): δ = 157.28, 156.66, 140.38, 139.22, 135.99, 134.41,
131.19, 124.60, 114.75 ppm. HRMS (ESI): calcd. for C4H4N5S [M
+ H]+ 216.0516; found 216.0516.
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Supporting Information (see footnote on the first page of this arti-
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Wentrup, J. Phys. Org. Chem. 2011, 24, 999–1008.
Received: September 9, 2013
cle): Detailed experimental procedures and characterization data
1
for some of the starting materials, H and 13C NMR and HRMS
spectra for the products.
Published Online: November 19, 2013
Eur. J. Org. Chem. 2014, 436–441
© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
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