Pyrroloindoles. 8. Electrophilic substitution in the 1H,5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole series

Autor: Kadzhrishvili, D. O., Samsoniya, Sh. A., Gordeev, E. N., Kurkovskaya, L. N., Zhigachev, V. E., Suvorov, N. N.
Zdroj: Chemistry of Heterocyclic Compounds; August 1983, Vol. 19 Issue: 8 p871-876, 6p
Abstrakt: The principles of the electron density distribution in 1H,5H-pyrrolo [2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole molecules were determined on the basis of quantumchemical calculations. These results were confirmed by the results of the investigated electrophilic-substitution reactions. The reaction centers of these compounds proved to be the same positions as in indole, viz., the 3 and 7 and 1 and 8 positions, respectively. The impossibility of 1,8-disubstitution in the angular heteroring was demonstrated in the case of bulky substituents; this was explained by a steric effect.
Databáze: Supplemental Index