J = 2.0 Hz, J = 4.4 Hz, 1H), 8.12 (dd, J = 1.6 Hz, J = 8.4 Hz,
147.08, 144.20, 141.97, 138.31, 136.06, 128.64, 127.68, 121.49,
114.63, 110.37, 107.08, 105.20, 40.93.
1
2
1
2
ACCEPTED MANUSCRIPT
1
H), 7.50 (d, J = 7.6 Hz, 2H), 7.44-7.30 (m, 5H), 7.11(d, J = 8.4
Hz, 1H), 6.70 (d, J = 7.6 Hz, 1H), 6.66 (s, br, 1H), 4.62 (d, J= 5.2
13
4.3.11 N-(Cyclohexylmethyl)quinolin-8-amine (5k). Yellow oil,
Hz, 2H); C NMR (100 MHz, CDCl ) δ: 146.98, 144.59, 139.26,
1
3
7
1
7
8% yield (75 mg). H NMR (400 MHz, CDCl ) δ: 8.75 (dd, J =
3
1
1
1
38.24, 136.08, 128.66, 127.80, 127.46, 127.18, 121.47, 114.19,
05.16, 47.73.
.6 Hz, J = 4.4 Hz, 1H), 8.09 (dd, J = 1.6 Hz, J = 8.0 Hz, 1H),
2
1
2
.43-7.38 (m, 2H), 7.05 (dd, J = 0.8 Hz, J = 8.0 Hz, 1H), 6.69
1
2
4
.3.5 N-(4-Methoxybenzyl)quinolin-8-amine (5e). Brown grey
(d, J = 7.2 Hz, 1H), 6.28 (s, br, 1H), 3.20 (t, J = 6.0 Hz, 2H), 1.97
(d, J = 13.2 Hz, 2H), 1.84-1.64 (m, 4H), 1.35-1.23 (m, 3H), 1.16-
1
solid, MP: 71-73 °C, 75% yield (79 mg). H NMR (400 MHz,
CDCl ) δ: 8.76 (dd, J = 1.6 Hz, J = 4.0 Hz, 1H), 8.11 (dd, J =
13
1.06 (m, 2H); C NMR (100 MHz, CDCl ) δ: 146.73, 145.12,
3
1
2
1
3
1
.6 Hz, J = 8.4 Hz, 1H), 7.43-7.37 (m, 4H), 7.10 (dd, J = 0.8 Hz,
138.19, 136.02, 128.73, 127.86, 121.35, 113.24, 104.38, 50.12,
37.47, 31.51, 26.63, 26.07.
2
1
J = 8.0 Hz, 1H), 6.94 (dt, J = 2.8 Hz, J = 9.2 Hz, 2H), 6.70 (d,
2
1
2
J = 7.6 Hz, 1H), 6.56 (s, br, 1H), 4.53 (d, J = 5.2 Hz, 2H), 3.85 (s,
13
4.3.12 N-(Cyclopropylmethyl)quinolin-8-amine (5l). Yellow oil,
3
1
1
H); C NMR (100 MHz, CDCl ) δ: 158.81, 146.93, 144.61,
38.23, 136.05, 131.21, 128.75, 128.65, 127.80, 121.44, 114.08,
14.03, 105.09, 55.34, 47.20.
1
3
6
1
7
0% yield (48 mg). H NMR (400 MHz, CDCl ) δ: 8.77 (dd, J =
3
1
.6 Hz, J = 4.0 Hz, 1H), 8.10 (dd, J = 2.0 Hz, J = 8.4 Hz, 1H),
2
1
2
.44-7.39 (m, 2H), 7.08 (dd, J = 0.8 Hz, J = 8.0 Hz, 1H), 6.69
1
2
4
.3.6
N-(4-(Trifluoromethyl)benzyl)quinolin-8-amine
(5f).
(d, J = 7.2 Hz, 1H), 6.28 (s, br, 1H), 3.20 (d, J = 6.0 Hz, 2H),
1
13
Yellow solid, MP: 68-70 °C, 88% yield (106 mg). H NMR (400
MHz, CDCl ) δ: 8.80 (dd, J = 1.6 Hz, J = 4.0 Hz, 1H), 8.13 (dd,
1.33-1.29 (m, 1H), 0.68-0.64 (m, 2H), 0.40-0.36 (m, 2H);
C
NMR (100 MHz, CDCl ) δ: 146.85, 144.97, 138.16, 136.04,
3
1
2
3
J = 1.6 Hz, J = 8.0 Hz, 1H), 7.64 (d, J = 8.4 Hz, 2H), 7.58 (d, J
128.70, 127.84,121.39, 113.70, 104.59, 48.50, 10.78, 3.73.
1
2
=
8.4 Hz, 2H), 7.45 (q, J = 4.0 Hz, 1H), 7.36 (t, J = 8.0 Hz, 1H),
Acknowledgement
7
.14 (dd, J = 0.8 Hz, J = 8.4 Hz, 1H), 6.76 (s, br, 1H), 6.60 (d, J
1 2
13
=
7.6 Hz, 1H), 4.68 (d, J = 6.0 Hz, 2H); C NMR (100 MHz,
We are grateful for financial support from the National
Natural Science Foundation of China (21202092) and for a
Startup Foundation from the China Three Gorges University
CDCl ) δ: 147.14, 144.16, 143.57, 138.20, 136.16, 129.56,
3
1
29.24, 128.67, 127.68, 127.40, 125.4 (d, J = 3.7 Hz), 125.56 (d,
F
JF = 3.9 Hz), 122.91, 121.60, 114.70, 105.30, 47.26.
(
KJ2012B080, KJ2014H008, 2016PY076).
4
.3.7 N-(2-Fluorobenzyl)quinolin-8-amine (5g). Yellow oil, 87%
1
Supplementary data
yield (88 mg). H NMR (400 MHz, CDCl3) δ: 8.79 (dd, J = 1.6
1
Hz, J = 4.4 Hz, 1H), 8.12 (dd, J = 1.6 Hz, J = 8.4 Hz, 1H), 7.48
2
1
2
Supplementary data associated with this article can be found
in the online version, at
(
td, J = 6.0 Hz, J = 7.6 Hz, 1H), 7.43 (q, J = 4.0 Hz, 2H), 7.38
1 2
(d, J = 8.0 Hz, 1H), 7.32-7.26 (m,1H), 7.15-7.10 (m, 3H), 6.71
(
6
1
dd, J = 0.4 Hz, J = 7.2 Hz, 1H), 6.65 (s, br, 1H), 4.69 (d, J =
.0 Hz, 2H); C NMR (100 MHz, CDCl3) δ: 162.21, 159.76,
1
2
13
References
47.05, 144.31, 138.26, 136.10, 129.23 (d, J = 4.4 Hz), 128.71
F
1
.
(a) Cuerva, J. M.; Campaña, A. G.; Justicia, J.; Rosales,
A.; Oller-López, J. L.; Robles, R.; Cádenas, D. J.;
Buñuel, E.; Oltra, J. E. Angew. Chem. Int. Ed. 2006, 45,
(d, J = 8.0 Hz), 127.77, 126.12 (d, J = 14.6 Hz), 124.22 (d, J =
F
F
F
3
.5 Hz), 121.50, 115.33 (d, J = 21.1 Hz), 114.43, 105.12, 41.12
F
(d, J = 4.7 Hz).
F
5
522-5526; (b) Campaña, A. G.; Estévez, R. E.;
Fuentes, N.; Robles, R.; Cuerva, J. M.; Buñuel, E.;
Cádenas, D.; Oltra, J. E. Org. Lett. 2007, 9, 2195-2198.
(a) Cummings, S. P.; Le, T.-N.; Fernandez, G. E.;
Quiambao, L. G.; Stokes, B. J. J. Am. Chem. Soc. 2016,
4
.3.8
N-(2-(Trifluoromethyl)benzyl)quinolin-8-amine
(5h).
1
Yellow solid, MP: 73-75 °C, 90% yield (109 mg). H NMR (400
MHz, CDCl ) δ: 8.80 (dd, J = 1.6 Hz, J = 4.0 Hz, 1H), 8.13 (dd,
2
3
.
3
1
2
J = 1.6 Hz, J = 8.0 Hz, 1H), 7.73 (dd, J = 7.6 Hz, J = 16.4 Hz,
1
2
1
2
1
38, 6107-6110; (b) Ojha, D. P.; Gadde, K.; Prabhu, K.
2
6
4
1
1
1
H), 7.51-7.33 (m, 4H), 7.12 (dd, J = 0.8 Hz, J = 8.0 Hz, 1H),
.78 (t, J = 5.6 Hz, 1H), 6.56 (dd, J = 0.8 Hz, J = 7.6 Hz, 1H),
.85 (d, J = 6.0 Hz, 2H); C NMR (100 MHz, CDCl ) δ: 147.11,
44.10, 138.21, 137.95, 136.13, 132.19, 128.67, 128.23, 127.97,
27.71(d, J = 8.0 Hz), 126.95, 126.02(t, J = 5.9 Hz), 123.31,
21.55, 114.57, 105.22, 43.89(d, J = 3.1 Hz).
1 2
R. Org. Lett. 2016, 18, 5062-5065.
1
2
13
.
.
(a) Xia, Y.-T.; Sun, X.-T.; Zhang, L.; Luo, K.; Wu, L.
Chem. Eur. J. 2016, 22, 17151-17155; (b) Xuan, Q.;
Song, Q. Org. Lett. 2016, 18, 4250-4253.
3
F
F
4
5
Kong, W.; Wang, Q.; Zhu, J. Angew. Chem. Int. Ed.
F
2
017, 56, 3987-3911.
4
.3.9 2-((Quinolin-8-ylamino)methyl)benzonitrile (5i). Yellow
. (a) Zhou, X.-F.; Sun, Y.-Y.; Wu, Y.-D.; Dai, J.-J.; Xu, J.;
Huang, Y.; Xu, H.-J. Tetrahedron 2016, 72, 5691-5698;
(b) Ding, W.; Song, Q. Org. Chem. Front. 2016, 3, 14-
18.
1
solid, MP: 112-114 °C, 80% yield (83 mg). H NMR (400 MHz,
CDCl ) δ: 8.80 (dd, J = 2.0 Hz, J = 4.4 Hz, 1H), 8.13 (dd, J =
1
7
7
3
1
2
1
.6 Hz, J = 8.4 Hz, 1H), 7.74 (dd, J = 0.8 Hz, J = 7.6 Hz, 1H),
.64 (d, J = 7.6 Hz, 1H), 7.55 (td, J = 1.2 Hz, J = 7.6 Hz, 1H),
.45 (q, J = 4.4 Hz, 1H), 7.41-7.34 (m, 2H), 7.14 (dd, J = 0.8 Hz,
2
1
2
1
1
2
6.
(a) Dowing, R. S.; Kunkeler, P. J.; Bekkum, H. V.
Catal. Today 1997, 37, 121-136; (b) Ono, N. Synthesis
2001, 16, 2528-2528; (c) Gunanathan, C.; Milstein, D.
Angew. Chem. Int. Ed. 2008, 47, 8661-8664; (d)
Kantam, M. L.; Chakravarti, R.; Pal, U.; Sreedhar, B.;
Bhargava, S. Adv. Synth. Catal. 2008, 350, 822-827; (e)
Liu, S.; Wang, Y.; Jiang, J.; Jin, Z. Green Chem. 2009,
1
J = 8.0 Hz, 1H), 6.85 (s, br, 1H), 6.71 (dd, J = 5.2 Hz, J = 92
2
1
2
13
Hz, 1H), 4.86 (d, J = 6.4 Hz, 2H); C NMR (100 MHz, CDCl3)
δ: 147.22, 143.81, 143.33, 138.20, 136.16, 133.16, 133.04,
1
1
28.65, 127.83, 127.65, 127.59, 121.64, 117.51, 114.99, 111.23,
05.35, 45.77.
1
1, 1397-1400; (f) Birch, A. M.; Groombridge, S.; Law,
4
6
2
7
6
.3.10 N-(Furan-2-ylmethyl)quinolin-8-amine (5j). Yellow Oil,
1
R.; Leach, A. G.; Mee, C. D.; Schramm, C. J. Med.
Chem. 2012, 55, 3923-3933; (g) Vishnoi, S.; Agrawal,
V.; Kasana, V. K. J. Agric. Food Chem. 2009, 57, 3261-
1% yield (55 mg). H NMR (400 MHz, CDCl ) δ: 8.77 (dd, J =
3
1
.0 Hz, J = 4.4 Hz, 1H), 8.11(dd, J = 1.6 Hz, J = 8.0 Hz, 1H),
2
1
2
.45-7.40 (m, 3H), 7.14 (dd, J = 1.2 Hz, J = 8.4 Hz, 1H),
1
2
3
265; (h) Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996,
.81(dd, J = 0.8 Hz, J = 7.6 Hz, 1H), 6.58 (s, br, 1H), 6.39-6.34
1
2
13
96, 2035-2052; (i) Pandarus, V.; Ciriminna, R.; Béland,
(m, 2H), 4.59 (s, 2H); C NMR (100 MHz, CDCl ) δ: 152.63,
3
7