Im, Jeong Kyun published the artcileN-Chlorinative Ring Contraction of 1,4-Dimethoxyphthalazines via a Bicyclization/Ring-Opening Mechanism, Application of 6-Bromo-1,4-dichlorophthalazine, the publication is Synthesis (2021), 53(10), 1760-1770, database is CAplus.
An unprecedented N-chlorinative ring contraction of 1,2-diazines was discovered and investigated with an electrophilic chlorinating reagent, trichloroisocyanuric acid (TCICA). Through optimization and mechanistic anal., the assisting role of n-Bu4NCl as an exogenous nucleophile was identified and the optimized reaction conditions were applied to a range of 1,4-dimethoxyphthalazine derivatives Also, an improvement of overall efficiency was demonstrated by the use of a labile O-silyl group. A bicyclization/ring-opening mechanism inspired by the Favorskii rearrangement was proposed and supported by the DFT calculations Furthermore, the efforts on scope expansion as well as the evaluation of other electrophilic promoters revealed that the newly developed ring contraction reactivity was a unique characteristic of 1,4-dimethoxyphthalazine scaffold and TCICA.
Synthesis published new progress about 240400-95-7. 240400-95-7 belongs to phthalazine, auxiliary class Chloride,Bromide,Phthalazine, name is 6-Bromo-1,4-dichlorophthalazine, and the molecular formula is C8H3BrCl2N2, Application of 6-Bromo-1,4-dichlorophthalazine.