Non-symmetric phenazines were synthesized via the Buchwald-Hartwig amination of ortho-bromoazobenzenes with anilines under micellar conditions, using the commercially available surfactant Kolliphor EL in water, followed by an acid-promoted 6π-electrocyclization-aromatization process. Two different synthetic pathways to obtain the ortho-bromo azo intermediates were explored, namely the palladium catalysed selective ortho bromination of azobenzenes and the diazo coupling of ortho-bromo diazonium salts with N,N-dimethylaniline, imidazole, phenol, sodium methanesulfinate and ethyl chloroformate.

Yousif, D., Monti, M., Papagni, A., Vaghi, L. (2020). Synthesis of phenazines from ortho-bromo azo compounds via sequential Buchwald-Hartwig amination under micellar conditions and acid promoted cyclization. TETRAHEDRON LETTERS, 61(46) [10.1016/j.tetlet.2020.152511].

Synthesis of phenazines from ortho-bromo azo compounds via sequential Buchwald-Hartwig amination under micellar conditions and acid promoted cyclization

Yousif D.;Monti M.;Papagni A.;Vaghi L.
2020

Abstract

Non-symmetric phenazines were synthesized via the Buchwald-Hartwig amination of ortho-bromoazobenzenes with anilines under micellar conditions, using the commercially available surfactant Kolliphor EL in water, followed by an acid-promoted 6π-electrocyclization-aromatization process. Two different synthetic pathways to obtain the ortho-bromo azo intermediates were explored, namely the palladium catalysed selective ortho bromination of azobenzenes and the diazo coupling of ortho-bromo diazonium salts with N,N-dimethylaniline, imidazole, phenol, sodium methanesulfinate and ethyl chloroformate.
Articolo in rivista - Articolo scientifico
Azobenzenes; Buchwald-Hartwig amination; Electrocyclization; Micellar synthesis; Phenazines
English
Yousif, D., Monti, M., Papagni, A., Vaghi, L. (2020). Synthesis of phenazines from ortho-bromo azo compounds via sequential Buchwald-Hartwig amination under micellar conditions and acid promoted cyclization. TETRAHEDRON LETTERS, 61(46) [10.1016/j.tetlet.2020.152511].
Yousif, D; Monti, M; Papagni, A; Vaghi, L
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/289469
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