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F. Bouchikhi et al.
PAPER
(3) Antonini, I.; Claudi, F.; Cristalli, G.; Franchetti, P.;
HRMS (ES+): m/z calcd for C13H10N5 [M + H]+: 236.0936; found:
236.0945.
Griffantini, M.; Martelli, S. J. Med. Chem. 1982, 25, 1258.
(4) Minikata, S.; Komatsu, M.; Ohshiro, Y. Synthesis 1992, 661.
(5) Minikata, S.; Itoh, S.; Komatsu, M.; Ohshiro, Y. Bull. Chem.
Soc. Jpn. 1992, 65, 2992.
1,9-Dihydropyrrolo[3¢,2¢:5,6]pyrido[2,3-b]indole (4) and 1H-
Pyrrolo[3¢,2¢:5,6]pyrido[1,2-a]benzimidazole (5)
Compound 3 (43.7 mg, 0.186 mmol) was heated at 300 °C under ar-
gon for 1 h. After cooling, the residue was purified by flash chroma-
tography (cyclohexane–EtOAc, 7:3, then 5:5) to give 4 (5.3 mg,
0.026 mmol, 14%) as a yellow gum and 5 (14.5 mg, 0.070 mmol,
38%) as a dark orange gum.
(6) Ferreira, I. C. F. R.; Queiroz, M.-J. R. P.; Kirsch, G.
Tetrahedron 2003, 59, 3737.
(7) Dajka-Halasz, B.; Monsieurs, K.; Elias, O.; Karolyhazy, L.;
Tapolcsanyi, P.; Maes, B. U. W.; Riedl, Z.; Hajos, G.;
Dommisse, R. A.; Lemière, G. L. F.; Kosmrlj, J.; Matyus, P.
Tetrahedron 2004, 60, 2283.
4
(8) Ferreira, I. C. F. R.; Queiroz, M.-J. R. P.; Kirsch, G.
Tetrahedron 2002, 58, 7943.
IR (KBr): 3420 cm–1 (NH).
(9) Lavecchia, G.; Berteina-Raboin, S.; Guillaumet, G.
Tetrahedron Lett. 2004, 45, 2389.
(10) Lan, J.-B.; Zhang, G.-L.; Yu, X.-Q.; You, J.-S.; Chen, L.;
1H NMR (400 MHz, DMSO-d6): d = 6.52 (1 H, dd, J1 = 3.5 Hz,
J2 = 2.0 Hz), 7.14 (1 H, ddd, J1 = 7.5 Hz, J2 = 7.0 Hz, J3 = 1.0 Hz),
7.31 (1 H, dd, J1 = 3.5 Hz, J2 = 2.5 Hz), 7.33 (1 H, ddd, J1 = 8.0 Hz,
J2 = 7.0 Hz, J3 = 1.0 Hz), 7.40 (1 H, d, J = 8.0 Hz), 8.09 (1 H, d,
J = 8.0 Hz), 8.61 (1 H, s), 11.28-11.30 (1 H, br s, NH), 11.34-11.38
(1 H, br s, NH).
13C NMR (125 MHz, DMSO-d6): d = 100.1, 110.4, 118.5, 119.7,
120.3, 123.3, 124.8 (CHarom), 110.8, 114.6, 121.5, 138.7, 147.5,
149.8 (Carom).
Yan, M.; Xie, R.-G. Synlett 2004, 1095.
(11) Batt, D. G.; Petraitis, J. J.; Sherk, S. R.; Copeland, R. A.;
Dowling, R. L.; Taylor, T. L.; Jones, E. A.; Magolda, R. L.;
Jaffee, B. D. Bioorg. Med. Chem. Lett. 1998, 8, 1745.
(12) Byth, K. F.; Culshaw, J. D.; Green, S.; Oakes, S. E.; Thomas,
A. P. Bioorg. Med. Chem. Lett. 2004, 14, 2245.
(13) Messaoudi, S.; Anizon, F.; Pfeiffer, B.; Prudhomme, M.
Tetrahedron 2005, 61, 7304.
HRMS (ES+): m/z calcd for C13H10N3 [M + H]+: 208.0875; found:
208.0892.
(14) Hugon, B.; Pfeiffer, B.; Renard, P.; Prudhomme, M.
Tetrahedron Lett. 2003, 44, 4607.
(15) Witkop, B.; Fiedler, H. Justus Liebigs Ann. Chem. 1947,
558, 91.
5
IR (KBr): 3420 cm–1 (NH).
(16) D’Ischia, M.; Prota, G. Gazz. Chim. Ital. 1986, 116, 407.
(17) Waterhouse, A. L.; Pessah, I. N.; Francini, A. O.; Casida,
J. E. J. Med. Chem. 1987, 30, 710.
1H NMR (400 MHz, DMSO-d6): d = 6.67 (1 H, d, J = 3.0 Hz), 7.24
(1 H, d, J = 3.0 Hz), 7.28 (1 H, d, J = 9.5 Hz), 7.42 (1 H, ddd,
J1 = 8.0 Hz, J2 = 7.0 Hz, J3 = 1.0 Hz), 7.51 (1 H, ddd, J1 = 8.0 Hz,
J2 = 7.0 Hz, J3 = 1.0 Hz), 7.84 (1 H, d, J = 8.0 Hz), 7.88 (1 H, d,
J = 9.5 Hz), 8.73 (1 H, d, J = 8.0 Hz), 12.40-12.48 (1 H, br s, NH).
13C NMR (100 MHz, DMSO-d6): d = 103.7, 107.7, 112.5, 118.5,
118.6, 120.2, 124.3, 127.0 (CHarom), 109.6, 126.7, 128.9, 143.5,
147.8 (Carom).
(18) Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem.
Rev. 1998, 98, 409.
(19) Mehta, L. K.; Parrick, J.; Payne, F. J. Chem. Soc., Perkin
Trans. 1 1993, 1261.
(20) Vera-Luque, P.; Alajarin, R.; Alvarez-Builla, J.; Vaquero,
J. J. Org. Lett. 2006, 8, 415.
(21) Schirok, H.; Figueroa-Pérez, S.; Thutewohl, M.; Paulsen,
H.; Kroh, W.; Klewer, D. Synthesis 2007, 251.
(22) Cheng, C.-C.; Chang, C.-P.; Yu, W.-S.; Hung, F.-T.; Liu,
Y.-I.; Wu, G.-R.; Chou, P.-T. J. Phys. Chem. A 2003, 107,
1459.
(23) Schneider, C.; Gueyrard, D.; Popowycz, F.; Joseph, B.;
Goekjian, P. G. Synlett 2007, 2237.
HRMS (ES+): m/z calcd for C13H10N3 [M + H]+: 208.0875; found:
208.0878.
References
(1) Toledo, L. M.; Lydon, N. B.; Elbaum, D. Curr. Med. Chem.
1999, 6, 775.
(2) Schneller, S. W.; Luo, J.-K. J. Org. Chem. 1980, 45, 4045.
Synthesis 2009, No. 5, 755–758 © Thieme Stuttgart · New York