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Molecules 2017, 22(5), 684; doi:10.3390/molecules22050684

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

1
Department of Industrial Chemistry ‘Toso Montanari’, Alma Mater Studiorum Università di Bologna Viale Del Risorgimento, Bologna 4402136, Italy
2
A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov st. 8, Kazan, Tatarstan 420088, Russia
*
Authors to whom correspondence should be addressed.
Academic Editor: Margaret A. Brimble
Received: 23 February 2017 / Revised: 19 April 2017 / Accepted: 20 April 2017 / Published: 26 April 2017
(This article belongs to the Special Issue Women in Organic Chemistry)
View Full-Text   |   Download PDF [1356 KB, uploaded 28 April 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. View Full-Text
Keywords: benzofurazans; aromatic substitution; 1,3-diaminobenzenes benzofurazans; aromatic substitution; 1,3-diaminobenzenes
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Micheletti, G.; Bordoni, S.; Chugunova, E.; Boga, C. C-C Coupling Reactions between Benzofurazan Derivatives and 1,3-Diaminobenzenes. Molecules 2017, 22, 684.

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