748 J ournal of Natural Products, 1997, Vol. 60, No. 7
Notes
(4) Dwuma-Badu, D.; Ayin, J . S. K.; Fiagbe, N. I. Y.; Knapp, J . E.;
Schiff, P. L., J r.; Slatkin, D. J . J . Pharm. Sci. 1978, 67, 433-
434.
(5) Ablordeppey, S. Y.; Hufford, C. D.; Borne, R. F.; Dwuma-Badu,
D. Planta Med. 1990, 56, 416-417.
(6) Tackie, A. N.; Sharaf, M. H. M.; Schiff, P. L., J r.; Boye, G. L.;
Crouch, R. C.; Martin, G. E. J . Heterocycl. Chem. 1991, 28,
1429-1435.
(7) Spitzer, T. D.; Crouch, R. C.; Martin, G. E.; Sharaf, M. H. M.;
Schiff, P. L., J r.; Tackie, A. N.; Boye, G. L. J . Heterocycl. Chem.
1991, 28, 2065-2070.
(8) Tackie, A. N.; Boye, G. L.; Sharaf, M. H. M.; Schiff, P. L., J r.;
Crouch, R. C.; Spitzer, T. D.; J ohnson, R. L.; Dunn, J .; Minick,
D.; Martin, G. E. J . Nat. Prod. 1993, 56, 653-670.
(9) Crouch, R. C.; Davis, A. O.; Spitzer, T. D.; Martin, G. E.; Sharaf,
M. H. M.; Schiff, P. L., J r.; Phoebe, C. H., J r.; Tackie, A. N. J
Heterocycl. Chem. 1995, 32, 1077-1080.
(10) Sharaf, M. H. M.; Schiff, P. L., J r.; Tackie, A. N.; Phoebe, C. H.,
J r.; Martin, G. E. J . Heterocycl. Chem. 1996, 33, 239-243.
(11) Cimanga, K.; De Bruyne, T.; Pieters, L.; Claeys, M.; Vlietinck,
A. Tetrahedron Lett. 1996, 37, 1703-1706.
(12) Sharaf, M. H. M.; Schiff, P. L., J r.; Tackie, A. N.; Phoebe, C. H.,
J r.; J ohnson, R. L.; Minick, D.; Andrews, C. W.; Crouch, R. C.;
Martin, G. E. J . Heterocycl. Chem. 1996, 33, 789-797.
(13) Molina, P.; Alajar´ın, M.; Vidal, A. J . Chem. Soc., Chem. Commun.
1990, 1277-1279.
(14) Molina, P.; Alajar´ın, M.; Vidal, A.; Sa´nchez-Andrada, P. J . Org.
Chem. 1992, 57, 929-939.
(15) Rzepa, H. S.; Molina, P.; Alajar´ın, M.; Vidal, A. Tetrahedron
1992, 48, 7425-7434.
(16) Holt, S. J .; Petrow, V. J . Chem. Soc. 1948, 922-924.
(17) Kaczmarek, L.; Balicki, R.; Nantka-Namirski, P.; Peczynska-
Czoch, W.; Modarsski, M. Arch. Pharm. (Weinheim) 1988, 321,
463-467.
(18) Peczynska-Czoch, W.; Pognan, F.; Kaczmarek, L.; Boratynski,
J . J . Med. Chem. 1994, 37, 3503-3510.
(19) Kamienska-Trela, K.; Kania, L.; Kaczmarek, L. THEOCHEM
1995, 347, 467-476.
liquors was removed under reduced pressure, and the
residual material was chromatographed on a silica gel
column using n-hexane/ethyl acetate (4:1, v/v) as eluent
to yield 2-anilinoquinoline14 (5) (0.26 g, 40%).
Quinindoline (4) was transformed into 5-methyl-5H-
indolo[2,3-b]quinoline (1) following the reported proce-
dure.16
Selected spectral data of compound 1: 13C NMR
(CDCl3, 75 MHz) δ 156.3 (C-5a), 155.6 (C-6a), 137.0 (C-
4a), 130.4 (C-3), 129.9 (C-1), 129.3 (C-8), 128.2 (C-10b),
128.0 (C-11), 124.0 (C-10a), 121.9 (C-1), 121.0 (C-10),
120.8 (C-11a), 119.9 (C-9), 117.7 (C-7), 114.1 (C-4), 33.0
(NCH3); 13C NMR (DMSO-d6, 75 MHz) δ 155.2 (C-5a),
155.1 (C-6a), 136.5 (C-4a), 130.5 (C-3), 129.8 (C-1), 128.8
(C-11), 128.6 (C-8), 126.8 (C-10b), 123.7 (C-10a), 121.7
(C-2), 121.3 (C-10), 120.1 (C-11a), 119.1 (C-9), 117.0 (C-
7), 114.7 (C-4), 32.6 (NCH3).
Ack n ow led gm en t. We gratefully acknowledge the
financial support of the Direccio´n General de Investi-
gacio´n Cient´ıfica y Te´cnica (Project No. PB95-1019).
Many thanks are also given to Francisco Ban˜o Pin˜ero
for his help in the preparation of 2-ethynylaniline.
Refer en ces a n d Notes
(1) Boye, G. L.; Ampofo, O. Proceedings of the First International
Symposium on Cryptolepine; University of Science and Technol-
ogy: Kumasi, Ghana, 1983.
(2) Oliver-Bever, B. Medicinal Plants in Tropical West Africa;
Cambridge University Press: Cambridge, 1986, p 41.
(3) Gellert, E.; Raymond-Hamet; Schlittler, E. Helv. Chim. Acta
1951, 34, 642-651.
NP970177F