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I. V. Barinov, V. A. Chertkov
The
electrophylic substitution in 4-phenyl-4H-cyclopenta[c]cinnoline
Abstract
4-Phenyl-4H-cyclopenta[c]cinnoline
(4) reacts with trifluoroacetic anhydride, N-chlorosuccinimide and
p-tolyldiazonium tetrafluoroborate to give the mixture and 3-substituted
derivatives. Compounds (4) reacts with a N-bromosuccin-imide and
tetranitrometane to give only the 1-substituted compounds. The 1- or
3-monosubstituted compounds reacts with excess of corresponding reagent to give
the disubstituted compounds. A series ab initio and DFT calculation of possible
cationic intermediates of (4) and its analogues and parent system have been
made.
Copyright (C) Chemistry Dept., Moscow State University, 2002
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