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Organic & Biomolecular Chemistry
Page 5 of 6
DOI: 10.1039/C6OB02566H
Journal Name
COMMUNICATION
J. F. Zhao, X. H. Duan, H. Yang and L. N. Guo, J. Org. Chem.,
2015, 80, 11149.
Y. C. Yuan, H. B. Yang, X. Y. Tang, Y. Wei, M. Shi, Chem. Eur. J.
2016, 22, 5146.
For selected reviews, see: (a) H. Egami and M. Sodeoka,
Angew. Chem. Int. Ed., 2014, 53, 8294; (b) R. M. Romero, T.
7.25 (m, 2H), 7.10-7.06 (m, 1H), 6.84 (d, J = 8.0 Hz, 1H), 4.38 (d,
J = 12.4 Hz, 1H), 3.84 (d, J = 12.4 Hz, 1H), 2.20 (s, 3H), 1.45-1.39
(m, 1H), 1.20-1.14 (m, 1H), 1.12-1.06 (m, 1H), 0.87-0.82 (m,
1H). 13C NMR (100 MHz, CDCl3) 159.3, 141.4, 138.1, 129.7,
128.2, 128.1, 127.7, 127.3, 126.9, 125.7, 123.0, 87.4, 59.8, 59.3,
36.7, 26.8, 14.2, 12.5. IR (EtOH) 2969, 2920, 2115, 1635,
1598, 1448, 1265, 1152, 1074, 1041, 995, 766, 700 cm-1. HRMS
(ESI) Calcd. for C20H19Br2N4O [M+H]+ requires: 488.9920, Found:
488.9918.
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6
H. Woste and K. Muniz, Chem. Asian J., 2014,
Shimizu and M. Kanai, Tetrahedron Lett., 2014, 55, 3727; (d)
R. I. McDonald, G. Liu and S. S. Stahl, Chem. Rev., 2011, 111
2981; (e) S. R. Chemler, Org. Biomol. Chem., 2009, , 3009;
9, 972; (c) Y.
,
7
(f) G. Li, S. R. S. S. Kotti and C. Timmons, Eur. J. Org. Chem.,
2007, 55, 2745.
(syn)-2-(1-azido-2-bromopropan-2-yl)-4-(1-
7
8
K. Wu, Y. Liang and N. Jiao, Molecules, 2016, 21, 352.
(a) F. Wang, X. Qi, Z. Liang, P. Chen and G. Liu, Angew. Chem.
Int. Ed., 2014, 53, 1881; (b) F. Wang, N. Zhu, P. Chen, J. Ye
and G. Liu, Angew. Chem. Int. Ed., 2015, 54, 9356; (c) N.
bromocyclopropyl)-4-phenyl-4H-benzo[d][1,3]oxazine (2a’)
A white solid, 44 mg, 45% yield, m. p. 120-123 oC. 1H NMR (400
MHz, CDCl3, TMS) 7.67-7.64 (m, 2H), 7.45-7.34 (m, 3H), 7.27-
7.25 (m, 2H), 7.09-7.03 (m, 1H), 6.80 (d, J = 7.6 Hz, 1H), 4.45 (d,
J = 12.4 Hz, 1H), 3.91 (d, J = 12.0 Hz, 1H), 2.13 (s, 3H), 1.46-1.40
(m, 1H), 1.24-1.18 (m, 1H), 1.13-1.07 (m, 1H), 0.88-0.82 (m,
1H). 13C NMR (100 MHz, CDCl3) 159.1, 141.8, 138.1, 129.7,
128.1, 127.6, 127.4, 126.9, 125.8, 122.8, 87.4, 59.9, 59.5, 36.7,
25.5, 14.1, 12.6. IR (EtOH) 2967, 2920, 2114, 1636, 1597,
1448, 1250, 1152, 1072, 994, 773, 699 cm-1. HRMS (ESI) Calcd.
for C20H19Br2N4O [M+H]+ requires: 488.9920, Found: 488.9918.
Zhu, F. Wang, P. Chen, J. Ye and G. Liu, Org. Lett., 2015, 17
,
3580; (d) W. Kong, E. Merino and C. Nevado, Angew. Chem.
Int. Ed., 2014, 53, 5078; (e) L. Xu, X. Q. Mou, Z. M. Chen and
S. H. Wang, Chem. Commun., 2014, 50, 10676; (f) C. Qin, Y.
Su, T. Shen, X. Shi and N. Jiao, Angew. Chem. Int. Ed., 2016,
55, 350; (g) Y. Yuan, T. Shen, K. Wang and N. Jiao, Chem.
Asian J. 2013, 8, 2932.
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(a) I. Sakurada, S. Yamasaki, M. Kanai and M. Shibasaki,
Tetrahedron Lett., 2000, 41, 2415;. (b) P. K. Prasad, R. N.
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X. Sun, X. Li, S. Song, Y. Zhu, Y. F. Liang and N. Jiao, J. Am.
Chem. Soc., 2015, 137, 6059.
Acknowledgements
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11 (a) A. Hassner, F. Boerwinkle and A. B. Lavy, J. Am. Chem.
We are grateful for the financial support from the National
Basic Research Program of China (973)-2015CB856603, and
the National Natural Science Foundation of China (20472096,
21372241, 21361140350, 20672127, 21421091, 21372250,
21121062, 21302203, 20732008 and 21572052).
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