J. H. Markgraf et al. / Tetrahedron 61 (2005) 9102–9110
9109
4.4.2. 9H-Indolo[3,2,1-de]phenanthridin-9-one (10).
Colorless solid (0.056 g, 83% from 5c): mp 229.5–
230.0 8C (CHCl3–pet. ether) [lit.11b mp 227 8C]; IR (film)
1666 cmK1; 1H NMR d 8.83 (1H, d, JZ8.0 Hz), 8.68 (1H,
d, JZ7.7 Hz), 8.30 (1H, d, JZ8.0 Hz), 8.15 (1H, d, JZ
7.7 Hz), 8.07–8.03 (2H, m), 7.81 (1H, t, JZ7.0 Hz), 7.67–
7.54 (3H, m), 7.49 (1H, t, JZ7.4 Hz); 13C NMR d 160.1,
138.6, 134.2, 133.8, 133.0, 129.3, 128.3, 128.1, 127.8,
126.4, 125.0, 124.5, 124.1, 122.5, 121.0, 120.8, 120.3,
117.3, 117.2; MS m/z 269 (MC100%).
grateful to Dr. Stefan Peukert (Aventis Pharmaceutical Co.)
for a gift of 3-bromo-2-pyridinecarboxylic acid. This work
was supported by a Senior Scientist Mentor Initiative Award
from The Camille and Henry Dreyfus Foundation, Inc.
Additional support was provided by the Williams College
Faculty Research Fund.
References and notes
4.4.3. 8H-[1,6]Naphthyridino[8,7,6-jk]carbazol-8-one
(12). Yellow solid (0.057 g, 88%): mp 196.0–196.5 8C; IR
(film) 1685 cmK1; 1H NMR d 9.04 (1H, dd, JZ4.6, 2.0 Hz),
8.89 (1H, dd, JZ8.0, 2.0 Hz), 8.77 (1H, dt, JZ8.0, 1.0 Hz),
8.58 (1H, dd, JZ8.0, 1.0 Hz), 8.15 (1H, d, JZ1.0 Hz), 8.13
(1H, d, JZ1.0 Hz), 8.09–8.05 (1H, m), 7.67–7.47 (4H, m);
13C NMR d 159.6, 153.9, 151.1, 138.2, 137.2, 135.4, 128.2,
126.6, 125.4, 124.6, 124.2, 123.7, 123.1, 122.8, 122.3,
121.0, 118.2, 117.3; MS m/z 270 (MC100%). HRMS for
C18H11N2O [MCH]C requires: 271.0871. Found:
271.0861.
1. Marion, L.; Manske, R. H. F. Can. J. Res. 1938, 16B, 432–437.
2. (a) Kuo, P.-C.; Shi, L.-S.; Damu, A. G.; Su, C.-R.; Huang,
C.-H.; Ke, C.-H.; Wu, J.-B.; Lin, A.-J.; Bastow, K. F.; Lee,
K.-H.; Wu, T.-S. J. Nat. Prod. 2003, 66, 1324–1327.
(b) Bettarini, F.; Borgonovi, G. E.; Fiorani, T.; Gagliardi, I.;
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N.; Names, J.; Cook, J. M. J. Org. Chem. 1989, 54, 2170–2178.
(e) Ohmoto, T.; Nikaido, T.; Koike, K.; Kohda, K.; Sankawa,
U. Chem. Pharm. Bull. 1988, 36, 4588–4592. (f) Fukamiya,
N.; Okano, M.; Aratani, T.; Negoro, K.; Lin, Y.-M.; Lee, K.-H.
Planta Med. 1987, 53, 140–143. (g) Fukamiya, N.; Okano, M.;
Aratani, T.; Negoro, K.; McPhail, A. T.; Ju-ichi, M.; Lee,
K.-H. J. Nat. Prod. 1986, 49, 428–434. (h) Anderson, L. A.;
Harris, A.; Phillipson, J. D. J. Nat. Prod. 1983, 46, 374–378.
(i) Guzman, F.; Cain, M.; Larscheid, P.; Hagen, T.; Cook,
J. M.; Schweri, M.; Skolnick, P.; Paul, S. M. J. Med. Chem.
1984, 27, 570–576. (j) Harris, A.; Anderson, L. A.; Phillipson,
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J. L. Lloydia 1972, 35, 177–180.
4.4.4. 8H-[2,6]Naphthyridino[4,3,2-jk]carbazol-8-one
(13). Pale yellow solid (0.022 g, 16%): mp 249.5–
1
250.0 8C; IR (film) 1677 cmK1; H NMR d 9.77 (1H, s),
8.94 (1H, d, JZ5.2 Hz), 8.84 (1H, d, JZ8.0 Hz), 8.48 (1H,
d, JZ5.2 Hz), 8.34 (1H, d, JZ8.0 Hz), 8.18 (1H, d, JZ
7.6 Hz), 8.13 (1H, d, JZ7.5 Hz), 7.67 (2H, m), 7.56 (1H, d,
JZ7.5 Hz); 13C NMR d 149.0, 146.2, 138.5, 128.5, 126.6,
125.7, 124.9, 124.8, 122.0, 121.5, 121.0, 120.2, 117.5,
115.2; MS m/z 270 (MC100%). Calcd for C18H10N2O: C,
79.99; H, 3.73; N, 10.36. Found: C, 79.61; H, 3.80; N, 10.11.
4.4.5. 8H-[2,7]Naphthyridino[4,3,2-jk]carbazol-8-one
(14). Colorless solid (0.035 g, 28%): mp 274.0–275.0 8C;
IR (film) 1674 cmK1; 1H NMR d 9.87 (1H, s), 8.97 (1H, d,
JZ2.0 Hz), 8.82 (1H, d, JZ8.0 Hz), 8.21 (2H, t, JZ
7.0 Hz), 8.14–8.08 (2H, m), 7.65 (2H, t, JZ8.0 Hz), 7.54
(1H, t, JZ7.0 Hz); 13C NMR d 159.4, 152.8, 152.4, 140.6,
138.6, 135.7, 128.8, 126.3, 125.6, 125.2, 124.7, 123.6,
122.7, 121.4, 121.7, 117.6, 116.2, 115.3; MS m/z 270
(MC100%), 242 (16). HRMS for C18H11N2O [MCCH]
requires: 271.0871. Found: 271.0864.
3. Berti, G.; Bonsignori, A.; Da Settimo, A. Ann. Chim. (Roma)
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4. Shipchandler, M. T.; Mitscher, L. A. J. Heterocycl. Chem.
1971, 8, 695–696.
5. (a) Suzuki, H.; Adachi, M.; Ebihara, Y.; Gyoutoku, H.; Furuya,
H.; Murakami, Y.; Okuna, H. Synthesis 2005, 28–32.
(b) Condie, G. C.; Bergman, J. J. Heterocycl. Chem. 2004, 41,
531–540. (c) Lindsley, C. W.; Wisnoski, D. D.; Wang, Y.;
Leister, W. H.; Zhao, Z. Tetrahedron Lett. 2003, 44,
4495–4498. (d) Czerwinski, K. M.; Zificsak, J. S.; Oberbeck,
M.; Randlett, C.; King, M.; Mennen, S. Synth. Commun. 2003,
33, 1225–1231. (e) Ma, Z.-Z.; Hano, Y.; Nomura, T.; Chen,
4.4.6. 8H-[1,7]Naphthyridino[5,6,7-jk]carbazol-8-one
(15). Colorless solid (0.025 g, 22%): mp 252.0–255.0 8C
1
with decomp.; IR (film) 1686 cmK1; H NMR d 8.96 (1H,
s), 8.81 (1H, d, JZ8.5 Hz), 8.48 (1H, d, JZ8.0 Hz), 7.93
(3H, q, JZ7.0 Hz), 7.66 (1H, s), 7.58 (1H, t, JZ8.0 Hz),
7.45 (2H, q, JZ7.0 Hz); 13C NMR d 158.1, 150.5, 143.8,
138.5, 133.6, 131.0, 130.3, 128.4, 126.8, 126.1, 125.4,
124.5, 124.3, 122.0, 121.0, 120.4, 117.8, 115.1; MS m/z 270
(MC100%), 242 (38), 121 (20). HRMS for C18H11N2O
[MCCH] requires: 271.0871. Found: 271.0859.
¨
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Acknowledgements
We thank our colleagues, Professors Thomas Smith and
David Richardson, for loan of equipment and helpful
discussions, Marie-Adele Sorel for technical assistance,
and Deborah Morandi for manuscript preparation. We are
6. (a) Markgraf, J. H.; Finkelstein, M.; Cort, J. F. Tetrahedron
1996, 52, 461–470. (b) Markgraf, J. H.; Snyder, S. A.;
Vosburg, D. A. Tetrahedron Lett. 1998, 39, 1111–1112.