D
Synlett
Z. Zhu et al.
Letter
Org. Biomol. Chem. 2013, 11, 6008. (f) Wang, H.; Li, X.; Wu, F.;
Wan, B. Tetrahedron Lett. 2012, 53, 681. (g) Singh, K. N.; Singh,
P.; Singh, P.; Maheshwary, Y.; Kessar, S. V.; Batra, A. Synlett
(15) (a) Tang, R.-Y.; Xie, Y.-X.; Xie, Y.-L.; Xiang, J.-N.; Li, J.-H. Chem.
Commun. 2011, 47, 12867. (b) Shirakawa, E.; Uchiyama, N.;
Hayashi, T. J. Org. Chem. 2011, 76, 25. (c) Song, R.-J.; Tu, Y.-Q.;
Zhu, D.-Y.; Zhang, F.-M.; Wang, S.-H. Chem. Commun. 2015, 51,
749.
2013, 24, 1963.
(
5) (a) Zheng, Z.; Dian, L.; Yuan, Y.; Zhang-Negrerie, D.; Du, Y.; Zhao,
K. J. Org. Chem. 2014, 79, 7451. (b) Matcha, K.; Antonchick, A. P.
Angew. Chem. Int. Ed. 2013, 52, 2082. (c) Narayan, R.; Matcha, K.;
Antonchick, A. P. Chem. Eur. J. 2015, 21, 14678.
6) (a) Nobuta, T.; Tada, N.; Fujiya, A.; Kariya, A.; Miura, T.; Itoh, A.
Org. Lett. 2013, 15, 574. (b) Huang, H.-Y.; Wu, H.-R.; Wei, F.;
Wang, D.; Liu, L. Org. Lett. 2015, 17, 3702. (c) Siddaraju, Y.;
Prabhu, K. R. Org. Biomol. Chem. 2015, 13, 11651.
(16) N-(1H-1,2,3-Benzotriazol-1-ylmethyl)-N-methylacetamide
(3a); Typical Procedure
A 50 mL Schlenk tube equipped with a stirrer bar was charged
with KI (16.6 mg, 0.1 mmol), benzotriazole (59.5 mg, 0.5 mmol),
DMA (2 mL), and K S O (270 mg, 1 mmol) under air. The
(
2
2
8
mixture was then stirred at 80 °C for 6 h (TLC monitoring),
poured into H O (20 mL), and extracted with EtOAc (3 ×). Then
2
(
d) Waghmode, N. A.; Kalbandhe, A. H.; Thorat, P. B.; Karade, N.
the organic phase was evaporated under vacuum, and the crude
product was purified by column chromatography [silica gel, PE–
N. Tetrahedron Lett. 2016, 57, 680. (e) Xu, J.; Zhang, P.; Li, X.;
Gao, Y.; Wu, J.; Tang, G.; Zhao, Y. Adv. Synth. Catal. 2014, 356,
3
EtOAc (10:1 to 2:1)] to give a colorless oil; yield: 98 mg (96%);
1
331. (f) Siddaraju, Y.; Lamani, M.; Prabhu, K. R. J. Org. Chem.
H NMR (400 MHz, CDCl ): d = 8.04 (d, J = 8.3 Hz, 1 H), 7.90 (d, J =
3
2
014, 79, 3856. (g) Dhineshkumar, J.; Lamani, M.; Alagiri, K.;
8.7 Hz, 1 H), 7.50 (t, J = 7.5 Hz, 1 H), 7.38 (t, J = 7.6 Hz, 1 H), 6.21 (s,
2 H), 3.11 (s, 3 H), 2.13 (s, 3 H).
N-[(6-Chloro-1H-1,2,3-benzotriazol-1-yl)methyl]-N-methy-
lacetamide (3b) and N-[(5-Chloro-1H-1,2,3-benzotriazol-1-
yl)methyl]-N-methylacetamide (3b′)
Prabhu, K. R. Org. Lett. 2013, 15, 1092. (h) Chen, L.; Shi, E.; Liu,
Z.; Chen, S.; Wei, W.; Li, H.; Xu, K.; Wan, X. Chem. Eur. J. 2011, 17,
4085.
(
7) (a) Brahma, S.; Ray, J. K. Tetrahedron 2008, 64, 2883. (b) Muzart,
J. Tetrahedron 2009, 65, 8313. (c) Ding, S.; Jiao, N. Angew. Chem.
Int. Ed. 2012, 51, 9226.
Combined yield: 113 mg (95%)
3b
1
(
8) Li, Y.; Xue, D.; Lu, W.; Wang, C.; Liu, Z.-T.; Xiao, J. Org. Lett. 2014,
Colorless oil; H NMR (400 MHz, CDCl ): δ = 7.92–7.85 (m, 2 H),
3
1
6, 66.
7.28 (d, J = 8.9 Hz, 1 H), 6.09 (s, 2 H), 3.07 (s, 3 H), 2.08 (s, 3 H);
C NMR (101 MHz, CDCl3): δ = 171.60, 144.66, 134.48, 133.03,
13
(
9) Lou, S.-J.; Xu, D.-Q.; Shen, D.-F.; Wang, Y.-F.; Liu, Y.-K.; Xu, Z.-Y.
Chem. Commun. 2012, 48, 11993.
10) Itoh, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16,
125.65, 120.47, 110.95, 57.72, 35.03, 21.60; HRMS: m/z [M +
+
(
(
(
Na] calcd for C10H11ClN NaO: 261.0514; found: 261.0512.
4
2
050.
3b′
1
11) Liu, J.; Yi, H.; Zhang, X.; Liu, C.; Liu, R.; Zhang, G.; Lei, A. Chem.
Commun. 2014, 50, 7636.
Colorless oil; H NMR (400 MHz, CDCl ): δ = 8.02 (s, 1 H), 7.88
3
(dd, J = 8.8, 1.4 Hz, 1 H), 7.48 – 7.43 (m, 1 H), 6.18 (d, J = 1.5 Hz, 2
12) (a) Guo, S.; Lu, L.; Gong, J.; Zhu, Z.; Xu, F.; Wei, Z.; Cai, H. Org.
Biomol. Chem. 2015, 13, 4426. (b) Guo, S.; Zhu, Z.; Lu, L.; Zhang,
W.; Gong, J.; Cai, H. Synlett 2015, 26, 543. (c) Guo, S.; Gong, J.;
Lu, L.; Zhu, Z.; Cai, H. Youji Huaxue 2015, 35, 1348. (d) Lu, L.;
Guo, S.; Xiong, Q.; Liu, S.; Li, X.; Cai, H. Synthesis 2014, 46, 2445.
13) Xia, Q.; Chen, W. J. Org. Chem. 2012, 77, 9366.
H), 3.12 (d, J = 1.8 Hz, 3 H), 2.13 (d, J = 1.8 Hz, 3 H); 13C NMR
(101 MHz, CDCl ): δ = 128.87, 118.91, 112.23, 57.83, 35.05,
21.63; HRMS: m/z [M + Na] calcd for C10H11ClN NaO: 261.0514;
found: 261.0512.
N-[(5,6-Dimethyl-1H-1,2,3-benzotriazol-1-yl)methyl]-N-
methylacetamide (3c)
Colorless oil; yield: 84 mg (72%); H NMR (400 MHz, CDCl ): δ =
7.76 (s, 1 H), 7.61 (s, 1 H), 6.15 (s, 2 H), 3.08 (d, J = 1.3 Hz, 3 H),
3
+
4
(
(
1
14) Lao, Z.-Q.; Zhong, W.-H.; Lou, Q.-H.; Li, Z.-J.; Meng, X.-B. Org.
Biomol. Chem. 2012, 10, 7869.
3
13
2.40 (d, J = 9.4 Hz, 6 H), 2.13 (d, J = 1.3 Hz, 3 H); C NMR (101
MHz, CDCl ): δ = 171.48, 138.40, 134.22, 118.62, 110.22, 57.32,
3
+
3
4.82, 21.75, 20.93, 20.43; HRMS: m/z [M + Na] calcd for
C12H16N NaO: 255.1216; found: 255.1219.
4
©
Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, A–D