Abstract
An efficient cascade reaction involving sulfonylation and [2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides was described for the synthesis of 3-aryl-2,4-disulfonyl-1H-pyrroles. The main highlight of this study is the introduction of a new dual-functional reactivity of arylsulfonyl methyl isocyanides as the sulfonyl source as well as a 1,3-dipolar reagent in the same reaction. This system is facilitated by Cs2CO3 mediation in DMSO and 100 °C conditions.
Highlights
Since its rst isolation from bone pyrolysis in 1857, the pyrrole unit was identi ed as a fundamental substructure of numerous important natural and bioactive unnatural products.[1]
Owing to the practicality and commercial accessibility of their compounds, isocyanides and p systems have been demonstrated to be attractive functionalities for heterocyclic cycloaddition reactions that due to appropriate atom-economy are considered as an ideal approach for the direct synthesis of substituted pyrroles.[8]
As our ongoing effort to explore the novel synthetic application of 1,1-dibromoalkenes, we have previously investigated the reaction of this alkenes with two reagents of alkyl isocyanides and sodium sul nates, which in the former, 3-(hetero) arylpropynamides furnished from a palladium-catalyzed crosscoupling reaction,[16] and the latter involved a sulfonylation to yield the desired 1-bromo-1-sulfonylalkenes.[17] gem-Dibromo-1alkenes, which can be generated from the treatment of aldehydes or ketones with CBr4/PPh3,18 can act as an alternative
Summary
Since its rst isolation from bone pyrolysis in 1857, the pyrrole unit was identi ed as a fundamental substructure of numerous important natural and bioactive unnatural products.[1]. As our ongoing effort to explore the novel synthetic application of 1,1-dibromoalkenes, we have previously investigated the reaction of this alkenes with two reagents of alkyl isocyanides and sodium sul nates, which in the former, 3-(hetero) arylpropynamides furnished from a palladium-catalyzed crosscoupling reaction,[16] and the latter involved a sulfonylation to yield the desired 1-bromo-1-sulfonylalkenes.[17] gem-Dibromo-1alkenes, which can be generated from the treatment of aldehydes or ketones with CBr4/PPh3,18 can act as an alternative Scheme 1 ASMIC as a dual-functional reactive starting material in the same reaction.
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