302941-71-5Relevant academic research and scientific papers
An efficient method for the synthesis of 1-chlorophenazines based on the selective cathodic reduction of 3,3,6,6-tetrachloro-1,2-cyclohexanedione
Guirado, Antonio,Cerezo, Alfredo,Andreu, Raquel,López Sánchez, José I.,Bautista, Delia
, p. 6747 - 6755 (2004)
An efficient method for the synthesis of 1-chlorophenazines has been established. It is based on the use of 3,6,6-trichloro-2-hydroxy-2-cyclohexen-1- one 4 as a synthetic equivalent of 3-chloro-1,2-benzoquinone 3. The intermediate 4 was prepared in near quantitative yield by electroreductive monodechlorination of 3,3,6,6-tetrachloro-1,2-cyclohexanedione 1, which is an inexpensive and easily available starting material. Efficient reactions of 4 with primary 1,2-phenylenediamines provided the corresponding 1,1,4-trichloro-1,2,3,4-tetrahydrophenazines 6, which were directly aromatized by treatment with 2,6-lutidine to give the title compounds in high yields. X-ray crystallographic structures for 1,1,4-trichloro-1,2,3,4-tetrahydro-6- methylphenazine 6f, 8-benzoyl-1,1,4-trichloro-1,2,3,4-tetrahydro-phenazine 6ea, and 1,7-dichlorophenazine 10db have been determined.
A new synthetic route to 1-chlorophenazines. The electrochemical monodechlorination of 3,3,6,6-tetrachloro-l,2-cyclohexanedione as a key step
Guirado,Cerezo,Andreu
, p. 6579 - 6582 (2007/10/03)
A convenient new method for the synthesis of 1-chlorophenazines has been established. The first step involves an almost quantitative electrochemical reduction of 3,3,6,6-tetrachloro-1,2-cyclohexanedione 1 to 3,6,6-trichloro-2-hydroxy-2-cyclohexen-1-one 2. The reaction of 2 with aromatic 1,2-diamines followed by aromatisation through treatment with 2,6-lutidine leads to the title compounds in high yields. (C) 2000 Elsevier Science Ltd.
