Pyrroloindoles. 8. Electrophilic substitution in the 1H,5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole series |
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Authors: | D O Kadzhrishvili Sh A Samsoniya E N Gordeev L N Kurkovskaya V E Zhigachev N N Suvorov |
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Institution: | (1) Tbilisi State University, 380028 Tbilisi;(2) D. I. Mendeleev Moscow Institute of Chemical Technology, 125047 Moscow |
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Abstract: | The principles of the electron density distribution in 1H,5H-pyrrolo 2,3-f]indole and 3H,6H-pyrrolo3,2-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.See 1] for communication 7.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1086–1091, August, 1983. |
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