Abstract
The monobromination of isomeric benzisatins and tetrahydrobenzisatins was studied. The structure of the products was demonstrated by 1H NMR spectroscopy. A CNDO/S calculation was carried out for the electronic structure of the starting compounds. The calculated data correctly predict the direction of the bromination with the exception of benz[e]isatin.
Literature cited
G. I. Zhungietu and M. A. Rekhter, Isatin and Its Derivatives [in Russian], Izd. Shtiinitsa, Kishinev (1977).
V. Galasso, G. Pellizer, and G. C. Pappalardo, "A carbon-13 NMR and CNDO/S study of 1,2-indandione and heterocyclic analogues," Org. Magn. Reson., 9, No. 7, 401–403 (1977).
A. P. Stankyavichyus, L. I. Mazhilis, V. N. Garalene, et al., "The Protective action of isatins upon hypobaric hypoxia," Khim-farm. Zh., No. 12, 31–34 (1981).
J. Braun, "Über das Tetrophan and seine Derivaten," Annalen., 451, No. 1, 1–54 (1926).
O. D. Zhilina, A. M. Vasil'ev, and L. B. Shagalov, "The bromination of 2–3-dimethyl [4, 5]benzindole," in: Abstracts of the First All-Union Conference on the Chemistry, Biochemistry, and the Pharmacology of Indole Derivatives, Tbilisi, May 17–19, 1986, Tbilisi (1986), p. 65.
V. A. Bolotin and L. I. Mazhilis, "A study of the UV spectra of benzisatins," Lit. Fiz. Sb., 27, No. 1, 113 (1987).
V. N. Garalene, L. I. Stankyavichyus, L. I. Mazhilis, et al., "The antihypoxic activity in the benzisatin series," Khim.-farm. Zh., No. 12, 1305–1308 (1986).
A. Etienne and A. Staehelin, "La benzo-isatine linéaire," Bull. Soc. Chim. France, 21, No. 6, 743–748 (1954).
Author information
Authors and Affiliations
Additional information
Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 23, No. 6, pp. 744–748, November–December, 1987.
Rights and permissions
About this article
Cite this article
Bolotin, V.A., Mahilis, L.I. & Stankyavichyus, A.P. Monobromination of benzisatins. Theor Exp Chem 23, 690–693 (1988). https://doi.org/10.1007/BF00534615
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00534615