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H. K. Kadam et al.
PAPER
(d) Pousset, J.-L.; Martin, M.-T.; Jossang, A.; Bodo, B.
1H NMR (400 MHz, DMSO-d6): δ = 3.87 (s 3 H), 7.16 (d, J = 8.8
Hz, 1 H), 7.41 (d, J = 8.4 Hz, 1 H), 7.46 (t, J = 8.4 Hz, 1 H), 7.71 (t,
J = 8.0 Hz, 1 H), 7.88 (s 1 H), 7.96 (d, J = 8.4 Hz, 1 H), 8.08 (d,
J = 8.0 Hz, 1 H), 9.04 (s, 1 H), 11.51 (s, 1 H).
13C NMR (100 MHz, DMSO-d6): δ = 56.1 (CH3), 105.8 (CH), 112.1
(CH), 117.0 (CH), 118.6 (Cq), 121.0 (Cq), 123.0 (CH), 123.8 (Cq),
127.4 (CH), 128.1 (CH), 129.1 (2 CH), 136.3 (Cq), 146.8 (Cq),
153.7 (Cq), 154.0 (Cq).
Phytochemistry 1995, 39, 735.
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Planta Med. 1996, 62, 22. (b) Kirby, G. C.; Paine, A.;
Warhurst, D. C.; Noamese, B. K.; Phillipson, J. D.
Phytother. Res. 1995, 9, 359. (c) Peczynska-Czoch, W.;
Pognan, F.; Kaczmarek, L.; Boratynski, J. J. Med. Chem.
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Totte, J.; Tona, L.; Kambu, K.; Berghe, D.-V.; Vlietinck, A.
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Kaczmarek, L.; Bielawska-Pohl, A.; Dus, D.; Wietrzyk, J.;
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LCMS: m/z = 249 [M + H]+.
HRMS: m/z [M + Na]+ calcd for C16H12N2ONa: 271.0864; found:
271.0847.
8-Chloro-6H-indolo[2,3-b]quinoline (4c)
Reaction time: 5 h; colorless solid; yield: 139 mg (55%); mp 296–
298 °C.
1H NMR (400 MHz, DMSO-d6): δ = 7.29 (d, J = 8.4 Hz, 1 H), 7.50–
7.52 (m, 2 H), 7.74 (t, J = 8.0 Hz, 1 H), 7.98 (d, J = 8.4 Hz, 1 H),
8.11 (d, J = 8.4 Hz, 1 H), 8.27 (d, J = 8.4 Hz, 1 H), 9.07 (s, 1 H),
11.86 (s, 1 H).
13C NMR (100 MHz, DMSO-d6): δ = 111.1 (CH), 117.6 (Cq), 119.7
(Cq), 120.3 (CH), 123.6 (CH), 123.7 (CH), 124.2 (Cq), 127.4 (CH),
128.6 (CH), 129.2 (CH), 129.5 (CH), 132.9 (Cq), 142.6 (Cq), 146.7
(Cq), 153.4 (Cq).
(11) Ho, T.-L.; Jou, D.-G. Helv. Chim. Acta 2002, 85, 3823.
(12) Haddadin, M. J.; Zerdan, R. M. B.; Kurth, M. J.; Fettinger,
J. C. Org. Lett. 2010, 12, 5502.
LCMS: m/z = 253 [M + H]+, 251 [M – H]+.
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60, 747. (b) Timari, G.; Soos, T.; Hajos, G. Synlett 1997,
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1999, 326. (d) Fresneda, P. M.; Molina, P.; Delgado, S.
Tetrahedron 2001, 57, 6197. (e) Shi, C.; Zhang, Q.; Wang,
K. K. J. Org. Chem. 1999, 64, 925. (f) Jonckers, T. H. M.;
van Miert, S.; Cimanga, K.; Bailly, C.; Colson, P.; De Pauw-
Gillet, M.-C.; Van den Heuvel, H.; Claeys, M.; Dommisse,
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HRMS: m/z [M + H]+ calcd for C15H10N2Cl: 253.0533; found:
253.0531.
Acknowledgment
We are grateful to the DST, New Delhi for financial assistance and
IISc., Bangalore for HRMS. Hari K. Kadam is also thankful to
CSIR, New Delhi for a NET Senior Research Fellowship and
Prakash T. Parvatkar is thankful to the UGC, New Delhi for the
award of the Dr. D. S. Kothari Postdoctoral Fellowship.
(14) Dhanabal, T.; Sangeetha, R.; Mohan, P. S. Tetrahedron
2006, 62, 6258.
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