3
591
Synthesis
L. El Blidi et al.
Paper
1
3
C NMR (75 MHz, CDCl , 25 °C): δ = 49.7 (CH N), 101.6 (CHarom),
C. H.; Greene, A. E.; Kanazawa, A. Bioorg. Med. Chem. Lett. 2008,
18, 2143. (f) Cinelli, M. A.; Morrell, A.; Dexheimer, T. S.; Scher, E.
S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2008, 51, 4609.
(g) Cinelli, M. A.; Cordero, B.; Dexheimer, T. S.; Pommier, Y.;
Cushman, M. Bioorg. Med. Chem. 2009, 17, 7145. (h) Cinelli, M.
A.; Morrell, A. E.; Dexheimer, T. S.; Agama, K.; Agrawal, S.;
Pommier, Y.; Cushman, M. Bioorg. Med. Chem. 2010, 18, 5535.
6) (a) Fox, B. M.; Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.;
Staker, B. L.; Stewart, L.; Cushman, M. J. Med. Chem. 2003, 46,
3
2
1
1
26.3 (C ), 127.6 (2 CHarom), 127.7 (CHarom), 127.8 (CHarom), 128.2 (Cq),
28.3 (CHarom), 129.0 (C ), 129.6 (CHarom), 130.5 (CHarom), 131.1
q
q
(CHarom), 132.7 (CHarom), 137.7 (C ), 140.1 (C ), 148.9 (C ), 153.7 (C ),
q q q q
1
61.2 (C=O).
HRMS (ESI ): m/z [M]+ calcd for C19H12N O: 284.0950; found:
2
+
2
84.1051.
(
2
-(Quinolin-3-ylmethyl)isoquinolin-1(2H)-one (17)
3275. (b) Cheng, K.; Rahier, N. J.; Eisenhauer, B. M.; Gao, R.;
Beige solid; yield: 23 mg (26%); mp 211 °C; R = 0.64 (cyclohexane–
EtOAc, 3:2).
f
Thomas, S. J.; Hecht, S. M. J. Am. Chem. Soc. 2005, 127, 838.
7) Warneke, J.; Winterfeldt, E. Chem. Ber. 1972, 105, 2120.
(
1
H NMR (300 MHz, CDCl , 25 °C): δ = 5.22 (s, 2 H, CH N), 6.48 (d, J =
(8) Corey, E. J.; Crouse, D. N.; Anderson, J. E. J. Org. Chem. 1975, 40,
3
2
7.5 Hz, 1 H, CH), 7.08 (d, J = 7.2 Hz, 1 H, CH), 7.25–7.32 (m, 6 H, 6
2140.
CHarom), 7.48–7.51 (m, 2 H, 2 CHarom), 7.63 (dd, J = 7.2, 7.6, 1 H, CHarom),
(9) Walraven, H. G. M.; Pandit, U. K. Tetrahedron 1980, 36, 321.
(10) Pin, F.; Comesse, S.; Sanselme, M.; Daïch, A. J. Org. Chem. 2008,
73, 1975.
8.47 (d, J = 8.3 Hz, 1 H, CHarom).
13
C NMR (75 MHz, CDCl , 25 °C): δ = 49.7 (CH N), 106.8 (CH), 126.0
3
2
(
(
(
11) Xu, X.; Liu, Y.; Park, C. M. Angew. Chem. Int. Ed. 2012, 51, 9372.
12) Pin, F.; Comesse, S.; Daïch, A. Synlett 2009, 3214.
13) For general reviews, see: (a) Bowman, W. R.; Bridge, C. F.;
Brookes, P. J. Chem. Soc., Perkin Trans. 1 2000, 1. (b) Bowman, W.
R.; Cloonan, M. O.; Krintel, S. L. J. Chem. Soc., Perkin Trans. 1
(
CH), 127.0 (C ), 127.05 (CHarom), 127.1 (CHarom), 127.2 (CHarom), 127.6
q
(
CHarom), 127.9 (CHarom), 128.0 (CHarom), 128.1 (C ), 130.5 (CHarom),
q
1
31.6 (CHarom), 132.5 (CHarom), 137.0 (C ), 137.8 (CHarom), 146.9 (Cq),
q
1
49.3 (C ), 162.2 (C=O).
q
HRMS (ESI ): m/z [M]+ calcd for C19H14N O: 286.1106; found:
+
2
2001, 2885. (c) Majumdar, K. C.; Basu, P. K.; Mukhopadhyay, P.
286.1022.
P. Tetrahedron 2004, 60, 6239. For reviews on the synthesis of
natural and unnatural compounds using radical cyclization, see:
(
1
d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91,
237. (e) Li, J. J. Alkaloids: Chemical Perspectives; Vol. 5;
Acknowledgment
Pelletier, S. W., Ed.; Wiley: New York, 2001, Chap. 4. (f) Renaud,
P.; Sibi, M. P. Radical in Organic Synthesis; Wiley-VCH: Wein-
heim, 2001. (g) Majumdar, K. C.; Mukhopadhyay, P. P.; Basu, P.
K. Heterocycles 2004, 63, 1903; and references therein.
We are grateful to French Ministry of Higher Education and Research
for a Graduate Fellowship, attributed to A.N. We are also grateful to
the University of Le Havre, especially to ‘UFR des Sciences et Tech-
niques’ for the ‘ATER position’, attributed to our colleagues L.E. and
A.B.
(h) Majumdar, K. C.; Basu, P. K.; Mukhopadhyay, P. P. Tetrahe-
dron 2005, 61, 10603.
(
14) (a) Orito, K.; Satoh, Y.; Nishizawa, H.; Harada, R.; Tokuda, M.
Org. Lett. 2000, 2, 2535. (b) Wakchaure, P. B.; Easwar, S.; Argade,
N. P. Synthesis 2009, 1667.
Supporting Information
(
15) (a) Nadin, A.; Harrison, T. Tetrahedron Lett. 1999, 40, 4073.
Supporting information for this article is available online at
(b) Bennasar, M.-L.; Juan, C.; Bosch, J. Chem. Commun. 2000,
http://dx.doi.org/10.1055/s-0034-1378811.
S
u
p
p
ortioIgnfrm oaitn
S
u
p
p
ortioIgnfrm oaitn
2459. (c) Bennasar, M.-L.; Zulaica, E.; Juan, C.; Alonso, Y.; Bosch,
J. J. Org. Chem. 2002, 67, 7465.
(
16) Comins, D. L.; Hoang, H.; Jianhua, G. Tetrahedron Lett. 1994, 35,
References
5331.
(
17) (a) Rahier, N. J.; Cheng, K.; Gao, R.; Eisenhauer, B. M.; Hecht, S.
M. Org. Lett. 2005, 7, 835. (b) Bowman, W. R.; Elsegood, M. R. J.;
Stein, T.; Weaver, G. W. Org. Biomol. Chem. 2007, 5, 103.
(
1) Wang, J. C. Nat. Rev. Mol. Cell Biol. 2002, 3, 430; and references
therein.
(2) (a) Pommier, Y. Nat. Rev. Cancer 2006, 6, 789. (b) Pommier, Y.
Chem. Rev. 2009, 109, 2894; and references therein.
(
18) (a) Caramella, P.; Bandiera, T.; Albini, F. M.; Gamba, A.; Corsaro,
A.; Perrini, G. Tetrahedron 1988, 44, 4917. (b) Izumi, T.;
Nishimoto, Y.; Kohei, K.; Kasahara, A. J. Heterocycl. Chem. 1990,
(c) Capranico, G.; Marinello, J.; Baranello, L. Biochim. Biophys.
Acta 2010, 1806, 240. (d) Khadka, D. B.; Cho, W.-J. Bioorg. Med.
Chem. 2011, 19, 724; and references therein.
27, 1419. (c) Lu, W.-D.; Lin, C.-F.; Wang, C.-J.; Wang, S.-J.; Wu,
M.-J. Tetrahedron 2002, 58, 7315. (d) Webb, N. J.; Marsden, S. P.;
Raw, S. A. Org. Lett. 2014, 16, 4718.
(
3) Adams, D. J.; Dewhirst, M. W.; Flowers, J. L.; Gamcsik, M. P.;
Colvin, O. M.; Manikumar, G.; Wani, M. C.; Wall, M. E. Cancer
Chemother. Pharmacol. 2000, 46, 263.
(19) For 5-substitued isoquinolines except the halogenated deriva-
tives, see: (a) Sunderland, P. T.; Woon, E. C. Y.; Dhami, A.;
Bergin, A. B.; Mahon, M. F.; Wood, P. J.; Jones, L. A.; Tully, S. R.;
Lloyd, M. D.; Thompson, A. S.; Javaid, H.; Martin, N. M. B.;
Threadgill, M. D. J. Med. Chem. 2011, 54, 2049. (b) Matsui, T.;
Suguira, T.; Nakai, H.; Iguchi, S.; Shigeoka, S.; Takada, H.;
Odagaki, Y.; Nagao, Y.; Ushio, Y.; Ohmoto, K.; Iwamura, H.;
Yamazaki, S.; Arai, Y.; Kawamura, M. J. Med. Chem. 1992, 35,
3307. (c) Li, S. W.; Nair, M. G.; Edwards, D. M.; Kisliuk, R. L.;
Gaumont, Y.; Dev, I. K.; Duch, D. S.; Humphreys, J.; Smith, G. K.;
Ferone, R. J. Med. Chem. 1991, 34, 2746.
(
4) (a) Advances in DNA Sequence-Specific Agents; Vol. 4; Jones, G.
B.; Chapman, B. J., Eds.; Elsevier: Amsterdam, 2002, 1. (b) Hecht,
S. M. Curr. Med. Chem. Anti-Cancer Agents 2005, 5, 353.
(c) Sequence-Specific DNA Binding Agents, 1st ed.; Waring, M.,
Ed.; RSC: Cambridge, 2006, 1–258.
(5) (a) Ma, Z.; Lee, D. Y. W. Tetrahedron Lett. 2004, 45, 6721.
(b) Babjak, M.; Kanazawa, A.; Anderson, R. J.; Greene, A. E. Org.
Biomol. Chem. 2006, 4, 407. (c) Xiao, X.; Antony, S.; Pommier, Y.;
Cushman, M. J. Med. Chem. 2006, 49, 1408. (d) Zhou, H.-B.; Liu,
G.-S.; Yao, Z.-J. J. Org. Chem. 2007, 72, 6270. (e) Grillet, F.;
Baumlova, B.; Prevost, G.; Constant, J.-F.; Chaumeron, S.; Bigg, D.
©
Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 3583–3592