An efficient method for the synthesis of 1-chlorophenazines based on the selective cathodic reduction of 3,3,6,6-tetrachloro-1,2-cyclohexanedione

Add time:07/18/2019    Source:sciencedirect.com

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.

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