C-C Coupling Reactions between Benzofurazan Derivatives and 1,3-Diaminobenzenes
Gabriele Micheletti1, Silvia Bordoni2, Elena Chugunova3
1Department of Industrial Chemistry 'Toso Montanari', Alma Mater Studiorum Università di Bologna Viale Del Risorgimento, Bologna 4402136, Italy. gabriele.micheletti3@unibo.it.
Abstract:
Aromatic substitution reactions between 1,3-diaminobenzene and chloronitrobenzofurazan derivatives have never been reported so far. The aim of the current study was to synthesize novel electron-donor and -acceptor architectures of interest in applied fields and to provide new insights on the nucleophilic behavior of 1,3-diaminobenzenes. The reaction of 1,3-dipiperidinyl-, 1,3-dimorpholinyl-, 1,3-dipyrrolidinyl-, or 1,3-dimethylamino-benzene with 7-chloro-4,6-dinitrobenzofuroxan or with a series of chloro-nitrobenzofurazans has been carried out in mild conditions. The partners reactivity has been investigated by monitoring the reaction course through ¹H-NMR spectroscopy. The reaction occurred in a regioselective way, providing in good yields the novel C-C coupling compounds. Indications on the reactivity behavior for the studied nucleophiles have been relieved.
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