Please do not adjust margins
Organic & Biomolecular Chemistry
Page 5 of 6
DOI: 10.1039/C5OB01659B
Journal Name
N-tert-butyl-5-methyl-7,8,9,10-tetrahydro-9-
aminophenanthridine, 3qa: yellow solid, m.p. = 97.7-98.8 C;
1H NMR (400 MHz, CDCl3) δ ppm 7.61-7.63 (d, J = 8.4 Hz, 1 H),
7.51 (s, 1 H), 7.30-7.32 (d, J = 8.0 Hz, 1 H), 4.32 (br s, 1 H), 2.98
ARTICLE
Acknowledgements
o
We gratefully acknowledge the National Science Foundation
of China (No. 21302152) and Northwest University for financial
(s, 2 H), 2.47 (s, 3 H), 2.42 (s, 2 H), 1.89 (s, 4 H), 1.59 (s, 9 H); support
13C NMR (101 MHz, CDCl3) δ ppm 154.5, 144.1, 139.7, 130.6,
129.6, 127.0, 122.7, 121.7, 118.5, 51.6, 29.5, 25.5, 24.5, 22.5,
22.1, 21.7; HRMS (ESI) m/z calcd for C18H24N2 (M+H)+ 269.2012,
Notes and references
found 269.2007.
N-tert-butyl-6-nitro-4-phenyl-2-aminoquinoline, 3ra: yellow
1
(a) K.Turner Org. Process Res. Dev. 2010, 14, 759. (b)
o
1
solid, m.p. = 217.6-219.9 C; H NMR (400 MHz, CDCl3) δ ppm
8.54 (s, 1 H), 8.28 (d, J = 8.8 Hz, 1 H), 7.72 (d, J = 9.2 Hz, 1 H),
2
(a) J. M. Harris, B. R. Neustadt, H. Liu, J. Hao, A. W. Stamford
Int. Patent WO 2009111442, 2009. (b) N. T. T. Osakada, S.
Uchida, S. Ono, N.Nakazato Jpn. Patent JP 2005132834,
2005.
7.42-7.51 (m, 5 H), 6.58 (s, 1 H), 5.01 (s, 1 H), 1.59 (s, 9 H); 13
C
NMR (101 MHz, CDCl3) δ ppm 157.9, 152.5, 150.2, 141.9,
137.1, 129.2, 129.9, 127.8, 123.4, 123.1, 120.7, 114.8, 52.4,
29.3. HRMS (ESI) m/z calcd for C19H19N3O2 (M+H)+ 322.1550,
found 322.1556.
N-tert-butyl-3,4-dihydro-3-methylene-2-aminoquinoline, 3sa:
1H NMR (400 MHz, CDCl3) δ ppm 7.16-7.17 (d, J = 4.4 Hz, 3 H),
7.05-7.07 (m, 1 H), 5.94-6.04 (m, 1 H), 5.02-5.06 (m, 2 H), 3.43-
3.45 (d, J = 6.4 Hz, 2 H), 1.40 (s, 9 H); 13C NMR (101 MHz,
CDCl3) δ ppm 139.1, 137.0, 135.9, 133.9, 130.1, 127.3, 124.8,
123.7, 115.7, 57.3, 36.0, 31.7; HRMS (ESI) m/z calcd for
C14H18N2 (M+H)+ 215.1543, found 215.1548.
3
4
E. Baxter Int. Patent WO 2009097278, 2009.
(a) D. E. Clark, C. Higgs, S. P. Wren, H. J. Dyke, M. Wong, D.
Norman, P. M. Lockey, A. G. Roach J. Med. Chem. 2004, 47,
3962. (b) J. Jiang, M. Hoang, J. R. Young, D. Chaung, R. Eid, C.
Turner, P. Lin, X. Tong, J. Wang, C. Tan, S. Feighner, O.
Palyha, D. L. Hreniuk, J. Pan, A. W. Sailer, D. L. MacNeil, A.
Howard, L. Shearman, S. Stribling, R. Camacho, A. Strack, L.
H. T. Van der Ploeg, M. T. Goulet, R. J. DeVita Bioorg. Med.
Chem. Let. 2006, 16, 5270.
5
(a) S. Kondo, R. Takai Org. Lett. 2003, 15, 538. (b) J.-S. Li, F.-X.
,
Chen, R. Shikiya, L. A. Marky, B. Gold J. Am. Chem. Soc. 2005
N-isopropyl-4-phenyl-2-aminoquinoline, 3ab: 1H NMR (400
MHz, CDCl3) δ ppm 7.73 (d, J = 8.4 Hz, 1 H), 7.62 (d, J = 8 Hz, 1
H), 7.47-7.55 (m, 6 H), 7.12-7.16 (m, 1 H), 6.56 (s, 1 H), 4.67 (d,
J = 7.2 Hz, 1 H), 4.20-4.25 (m, 1 H), 1.30 (d, J = 6.4 Hz, 6 H);13C
NMR (101 MHz, CDCl3) δ ppm 156.1, 149.38, 148.9, 138.7,
129.6, 129.4, 128.5, 128.2, 126.5, 125.8, 122.4, 122.0, 111.2,
43.0, 23.3. HRMS (ESI) m/z calcd for C18H18N2 (M+H)+ 263.1543,
found 263.1538.
127, 12657. (c) K. Nakatani, S. Sando, H. Kumasawa, J.
Kikuchi, I. Saito J. Am. Chem. Soc. 2001, 123, 12650. (d) K.
Nakatani, S. Sando, I. Saito J. Am. Chem. Soc. 2000, 122,
2172.
C. K. McGill, A. Rappa Adv. Heterocycl. Chem. 1988, 44, 1.
(a) S. R. Inglis, C. Stojkoski, K. M. Branson, J. F. Cawthray, D.
Fritz, E. Wiadrowski, S. M. Pyke, G. W. Booker J. Med. Chem.
2004, 47, 5405. (b) M. A. Cinelli, H. Li, G. Chreifi, P. Martasek,
6
7
L. J. Roman, T. L. Poulos, R. B. Silverman J. Med. Chem. 2014
,
N-n-hexyl-4-phenyl-2-aminoquinoline, 3ac: 1H NMR (400 MHz,
CDCl3) δ ppm 7.74 (d, J = 8.4 Hz, 1 H), 7.62 (d, J = 8.0 Hz, 1 H),
7.47-7.53 (m, 6 H), 7.12-7.16 (m, 1 H), 6.58 (s, 1 H), 4.81 (br s, 1
H), 3.46-3.51 (m, 2 H), 1.64-1.71 (m, 2 H), 1.42-1.46 (m, 2 H),
1.32-1.35 (m, 4 H), 0.89-0.92 (m, 3 H); 13C NMR (101 MHz,
CDCl3) δ ppm 156.8, 149.8, 148.8, 138.7, 129.6, 129.4, 128.5,
128.3, 126.5, 125.9, 122.5, 122.0, 111.0, 42.1, 31.7, 29.9, 26.9,
22.7, 14.2. HRMS (ESI) m/z calcd for C21H24N2 (M+H)+ 305.2013,
found 305.2005.
57, 1513. (c) S. Inglis, R. Jones, D. Fritz, C. Stojkoski, G.
Booker, S. Pyke Org. Biomol. Chem. 2005, 3, 2543. (d) J.-S. Li,
F.-X. Chen, R. Shikiya, L. A. Marky, B. Gold J. Am. Chem. Soc.
2005 ,127, 12657.
8
(a) S. Ge, R. A. Green, J. F. Hartwig J. Am. Chem. Soc. 2014,
136, 1617. (b) C. W. Cheung, D. S. Surry, S. L. Buchwald Org.
Lett., 2013, 15, 3734. ( c) L. Nicolas, P. Angibaud, I. Stansfield,
L. Meerpoel, S. Reymond, J. Cossy RSC Adv. 2013, 3, 18787.
(d) D. Maiti, B. P. Fors, J. L. Henderson, Y. Nakamura, S. L.
Buchwald Chem. Sci. 2011, 2, 57. (e) S. Breitler, N. J.
Oldenhuis, B. P. Fors, S. L. Buchwald Org. Lett. 2011, 13,
3262. (f) Q. Shen, J. F. Hartwig Org. Lett. 2008, 11, 4109. (g)
Q. L. Shen, S. Shekhar, J. P. Stambuli, J. F. Hartwig Angew.
Chem., Int. Ed. 2005, 44, 1371.
(a) J. Yin, B. Xiang, M. A. Huffman, C. E. Raab, I. W. Davies J.
Org. Chem. 2007, 72, 4554. (b) M. Couturier, L. Caron, S.
Tumidajski, K. Jones, T. D. White Org. Lett. 2006, 8, 1929. (c)
T. Storz Org. Proc. Res. Dev. 2004, 8, 663. (d) Y. Miura, S.
Takaku, Y. Fujimura, M. Hamana Heterocycles 1992, 34,
1055.
N-(2,6-diisopropylphenyl)-4-phenyl-2-aminoquinoline, 3ae:
o
1
pink solid, m.p. = 227.2-228.8 C; H NMR (400 MHz, CDCl3) δ
ppm 7.60 (d, J = 8.4 Hz, 1 H), 7.43-7.52 (m, 2 H), 7.23-7.34 (m,
6 H), 7.14-7.16 (m, 2 H), 7.08 (t, J = 7.2 Hz, 1 H), 6.90 (br s, 1 H),
6.17 (s, 1 H), 3.22-3.29 (m, 2 H), 1.07 (d, J = 5.2 Hz, 12 H); 13
C
9
NMR (101 MHz, CDCl3) δ ppm 157.5, 150.7, 148.6, 148.2,
138.6, 133.0, 129.9, 129.3, 128.5, 128.4, 128.2, 126.2, 126.1,
124.2, 122.8, 122.3, 108.9, 31.1, 28.6. HRMS (ESI) m/z calcd for
C27H28N2 (M+H)+ 381.2326, found 381.2319.
5-phenyl-2,3-di-(2,4,6-trimethylphenylimino)-1H-
10 (a) G. Li, C. Jia, K. Sun Org. Lett. 2013, 15, 5198. (b) C. Zhu, M.
Yi, D. Wei, X. Chen, Y. Wu, X. Cui Org. Lett. 2014, 16, 1840.
11 (a) K. Wang, E. Herdtweck, A. Domling ACS Com. Sci. 2012, 14,
316. (b) T. H. Althuis, P. F. Moore, H. J. Hess J. Med. Chem.
1979, 22, 44.
benzo[b]azepine, 3af: pink solid, m.p. = 192.5-193.7 oC; 1H
NMR (400 MHz, CDCl3) δ ppm 9.59 (s, 1 H), 7.89 (d, J = 8.4 Hz, 1
H), 7.73 (d, J = 8.4 Hz, 1 H), 7.63-7.67 (m, 1H), 7.46-7.48 (m, 3
H), 7.31-7.38 (m, 3 H), 7.06 (s, 2 H), 6.87 (s, 2 H), 6.39 (s, 1 H),
2.34 (s, 3 H), 2.28 (s, 3 H), 2.27 (s, 6 H), 2.19 (s, 6 H); 13C NMR
(101 MHz, CDCl3) δ ppm 152.9, 151.2, 149.8, 147.9, 147.7,
138.5, 138.2, 136.7, 133.6, 132.0, 130.1, 129.6, 128.8, 128.7,
128.6, 128.5, 128.3, 125.8, 124.3, 124.2, 110.5, 31.1, 21.4,
20.8, 19.1, 18.8, 18.1. HRMS (ESI) m/z calcd for C34H33N3
(M+H)+ 484.2748, found 484.2768.
12 (a) K. J. Wiggall, S. K. Richardson, J. Heterocycl. Chem. 1995
,
32, 867. (b) P. Molina, M. Alajarin, A. Vidal, P. Sanchez-
Andrada J. Org. Chem. 1992, 57, 929. (c) G. Gast, J. Schmutz,
D. Sorg, HeIv. Chim. Acta, 1977, 60, 1644.
13 (a) J.-R. Chen, X.-Q. Hu, L.-Q. Lu, W.-J. Xiao Chem. Rev. 2015
,
115, 5301. (b) V. Boyarskiy, N. A. Bokach, K. Luzyanin, V. Y.
Kukushkin, Chem. Rev. 2015, 115, 2698. (c) T. Vlaar, B. U. W.
Maes, R. V.A. Orru Angew. Chem., Int. Ed. 2013, 52, 7084. (d)
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins