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Chlorination of isatins with Trichloroisocyanuric acid (TCCA)

Chlorination of isatins with Trichloroisocyanuric acid (TCCA)
isatin and its derivatives have been extensively reported in the literature as having range of potential pharmacological compounds. the sandmeyer method is the most widely used for isatin synthesis and furnishes different substituted isatins, usually with high yields. although efficient, the sandmeyer route has certain limitations, such as the formation of a mixture of regiosiomers and low yields depending on the type and position of the substituent. thus, overcome these limitations, it is preferable that some derivative isatins be obtained by alternative methods. this article has investigated the chlorination of isatin derivatives using trichloroisocyanuric acid [1,3,5-trichloro 1,3,5-triazine-2,4,6-(1h,3h,5h)-trione or tcca] at different reaction conditions.
Trichloroisocyanuric acid in 98% sulfuric acid: A superelectrophilic medium for chlorination of deactivated arenes
Trichloroisocyanuric acid (TCCA) reacts with arenes and its reactivity is highly affected by the acid strength of the reaction medium. Deactivated arenes are efficiently chlorinated by TCCA in HSO. Our results, along with DFT calculations and C NMR spectrometry suggest the formation of a monoprotonated TCCA superelectrophile as the reactive species that can efficiently transfer electrophilic Clto even very weak nucleophiles, such as -dinitrobenzene.