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.

Micheletti, G., Bordoni, S., Chugunova, E., Boga, C. (2017). C-C Coupling Reactions between Benzofurazan Derivatives and 1,3-Diaminobenzenes. MOLECULES, 22(5), 684-695 [10.3390/molecules22050684].

C-C Coupling Reactions between Benzofurazan Derivatives and 1,3-Diaminobenzenes

MICHELETTI, GABRIELE;BORDONI, SILVIA;BOGA, CARLA
2017

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.
2017
Micheletti, G., Bordoni, S., Chugunova, E., Boga, C. (2017). C-C Coupling Reactions between Benzofurazan Derivatives and 1,3-Diaminobenzenes. MOLECULES, 22(5), 684-695 [10.3390/molecules22050684].
Micheletti, Gabriele; Bordoni, Silvia; Chugunova, Elena; Boga, Carla
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/601200
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