5
2.0 Hz, 1H), 7.15-7.24 (m, 2H), 3.98 (s, 3H). 13C NMR (CDCl3,
8.
(a) Wu, X. -F.; Neumann, H.; Neumann, S.; Beller, M. Chem.
ACCEPTED MANUSCRIPT
Eur. J. 2012, 18, 8596-8599; (b) Rao, K. P.; Basak, A. K.; Deb, P.
K.; Sharma, S.; Reddy, L. K. Tetrahedron Lett. 2013, 54, 3694-
3696; (c) Suresh, A. S.; Baburajan, P.; Ahmed, M. Tetrahedron
Lett. 2014, 55, 3482-3485.
Wang, H.; Cai, J.; Huang, H.; Deng, G. -J. Org. Lett. 2014, 16,
5324-5327.
100 MHz): δ 162.7, 161.6 (d, JCF = 245 Hz), 159.1, 138.2, 130.4,
128.1, 127.5 (d, JCF =8.7 Hz), 123.7, 123.5, 122.9, 115.5 (d, JCF
=
22.7 Hz), 107.2, 56.0. HRMS (ESI) Calcd for C15H12FN2O2
[M+H]+: 271.0883; Found: 271.0895.
9.
6-Fluoro-2-(4-methoxyphenyl)phthalazin-1(2H)-one (3w)
10. (a) Munday, R. H.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem.
Soc. 2008, 130, 2754–2755; (b) Li, B.-J.; Yu, D.-G.; Sun, C.-L.;
Shi, Z.-J. Chem. Eur. J. 2011, 17, 1728-1759; (c) Reeves, D. C.;
Rodriguez, S.; Lee, H.; Haddad, N.; Krishnamurthy, D.;
Senanayake, C. H. Org. Lett. 2011, 13, 2495–2497; (d) Ueda, T.;
Konishi, H.; Manabe, K. Tetrahedron Lett. 2012, 53, 5171-5175;
(e) Chung, S.; Sach, N.; Choi, C.; Yang, X.; Drozda, S. E.; Singer,
R. A.; Wright, S. W. Org. Lett. 2015, 17, 2848-2851; (f) Fu, W.
C.; So, C. M.; Yuen, O. Y.; Lee, I. T. C.; Kwong, F. Y. Org. Lett.
2016, 18, 1872-1875.
Gray solid; mp 189.1 oC; 1H NMR (CDCl3, 400 MHz): δ 8.50-
8.54 (m, 1H), 8.22 (s, 1H), 7.47-7.55 (m, 3H), 7.38 (dd, J = 8.1,
2.4 Hz, 1H), 6.96-7.02 (m, 2H), 3.86 (s, 3H). 13C NMR (CDCl3,
100 MHz): δ 165.5 (d, JCF = 254 Hz), 159.0, 158.6, 137.2, 134.6,
134.4, 131.6 (d, JCF = 9.4 Hz), 130.7 (d, JCF = 9.6 Hz), 126.9,
120.5 (d, JCF = 23.3 Hz), 114.0, 111.2 (d, JCF = 21.9 Hz), 55.5.
HRMS (ESI) Calcd for C15H12FN2O2 [M+H]+: 271.0883; Found:
271.0887.
11.
Liu, B.; Wang, Y.; Liao, B.; Zhang, C.; Zhou, X. Tetrahedron
Lett. 2015, 56, 5776-5780.
Hydralazine hydrochloride (4)
12. (a) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc.
2003, 125, 11818-11819; (b) Kozhushkov, S. I.; Potukuchi, H. K.;
Ackermann, L. Catal. Sci. Technol. 2013, 3, 562-571; (c) Zhang,
Y.; Lavigne, G.; Cesar, V. J. Org. Chem. 2015, 80, 7666-7673.
13. (a) Nelson, D. J. U.S. Patent 20050137397, 2005; Chem. Abstr.
2005, 143, 78195; (b) Gowtham, S.; C. P. Babu R.; Chakrabhavi,
D. M.; Ameya, S.; Trang T. T. C.; Sebastian, A.; Huang, X.; Julian,
E. F.; Andreas, B.; Kanchugarakoppal, S. R.; Rajesh, C.; Basappa,
Bioorg. Med. Chem. Lett. 2016, 26, 3300–3306; (c) Ahmed MD,
A.; Luis MD, Q.; Noella MD, B. Am. J. Ther. 2016, 23, 1094-
1095; (d) Veau, D.; Krykun, S.; Mori, G.; Orena, B. S.; Pasca, M.
R.; Frongia, C.; Lobjois, V.; Chassaing, S.; Lherbet, C.; Baltas, M.
Chemmedchem 2016, 11, 1078-1089.
14. Zhao, B. -H.; Lin, J. -M. Chin. J. Org. Chem. 2011, 31, 1914-1916.
15. (a) Outerbridge, V. M.; Landge, S. M.; Tamaki, H.; Torok, B.
Synthesis 2009, 11, 1801-1806; (b) Shi, L.; Hu, L.; Wang, J.; Cao,
X.; Gu, H. Org. Lett. 2012, 14, 1876-1879; (c) Wang, Y.; Yang, Z.
-Y.; Wang, Q.; Cai, Q. -K.; Yu, K. -B. J. Organomet. Chem. 2005,
690, 4557-4563.
Pale yellow solid; mp 277.0 oC (Lit.[14] 272-274 oC); 1H NMR
(D2O, 400 MHz): δ 8.61 (s, 1H), 8.01-8.09 (m, 2H), 7.94-8.01 (m,
2H). 13C NMR (D2O, 100 MHz): 152.4, 144.9, 136.6, 134.7,
128.9, 127.6, 123.5, 118.6. HRMS (ESI) Calcd for C8H9N4 [M-
Cl]+: 161.0827; Found: 161.0822.
Acknowledgements
We thank the National Natural Science Foundation of China,
973 program (2015CB856600) and the Research Fund for the
Doctoral Program of Higher Education of China
(2013007113009) for financial support.
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