Abstract
The possibility of an electrophilic substitution reaction in the lilolidene series is shown. It is established that, when 2, 3-dimethyl-1, 7-trimethyleneindole (9, 10-dimethyl-9-lilolidene) is nitrated, the main product is the 5-nitro derivative with some of the 6-nitro isomer. The structure of the compounds obtained is established by the combined use of UV and NMR spectra. The conditions for the dehydrogenation of lilodines to lilolidenes are found. It is shown that the indoline system is dehydrogenated more readily than the tetrahydroquinoline system. The nitro compounds obtained are reduced to the corresponding amines by hydrazine hydrate in the presence of Raney nickel.
Similar content being viewed by others
References
A. N. Kost and L. G. Yudin, Khim. nauka i prom., 2, 800, 1957.
L. G. Yudin, A. N. Kost, and Yu. A. Berlin, Khim. nauka i prom., 3, 406, 1958.
A. N. Kost, L. G. Yudin, and A. P. Terent'ev, ZhOKh, 29, 1949, 1959.
A. N. Kost, L. G. Yudin, Yu. A. Berlin, and A. P. Terent'ev, ZhOKh, 29, 3820, 1959.
A. N. Kost, L. G. Yudin, B. A. Dmitriev, and A. P. Terent'ev, ZhOKh, 29, 3977, 1959.
A. N. Kost, L. G. Yudin, and S. A. Popravko, ZhOKh, 32, 1544, 1962.
L. G. Yudin, S. A. Popravko, and A. N. Kost, ZhOKh, 32, 3586, 1962.
H. Bauer and E. Strauss, Ber., 65, 308, 1932.
W. Noland, H. Smith, and D. Johnson, J. Org. Chem., 28, 2534, 1962.
G. Berti, A. da Settimo, and D. Segnini, Gazz., 90, 539, 1960.
R. Hinman and E. Whipple, J. Am. Chem. Soc., 84, 2534, 1962.
A. P. Terent'ev, M. N. Preobrazhenskaya, A. S. Bobkov, and G. M. Sorokina, ZhOKh, 29, 2541, 1959.
G. Pappalardo and T. Vitali, Gazz., 88, 564, 1958.
J. M. Jackman, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed., Pergammon Press, p. 58, 1962.
A. P. Terent'ev and M. N. Preobrazhenskaya, DAN, 118, 302, 1958.
K. Brown and A. Katritzky, Tetr. Letters, 14, 803, 1964.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kost, A.N., Yudin, L.G. & Budylin, V.A. The chemistry of indole. Chem Heterocycl Compd 2, 29–33 (1966). https://doi.org/10.1007/BF00955590
Issue Date:
DOI: https://doi.org/10.1007/BF00955590