Hard and soft electrophilic and nucleophilic dissymmetry of 𝛼-oxoketenedithioacetals and 𝑝-nitro-𝑜-phenylenediamine exploited to achieve the regioselectivity in the synthesis of 2-thiomethyl ether substituted isomer of the privileged nucleus of 1,5-benzodiazepines over to its 4-substituted isomers
An exclusive regioselective formation of 2-thiomethyl ether substituted isomer of the privileged nucleus of 1,5-benzodiazepines was achieved from the reaction of 𝑝-nitro-𝑜-phenylenediamine with a variety of 𝛼-oxoketene dithioacetals derived from several active methylene compounds, by exploiting the strategy based on the variation of electrophilicity of the two electrophilic centers of 𝛼-oxoketene dithioacetals and the hard and soft nucleophilic profiles of the 𝑝-nitro substituted 𝑜-phenylenediamines.
Volume 132, 2020
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