A transition
metal-free protocol for the preparation of fluorescent
and non-fluoresent 3-methylthio-4-arylmaleimides in a single step
through a new rearrangement from thiazolidine-2,4-diones is described.
By employing the optimized reaction conditions, a broad scope of derivatives
was prepared in ≤97% yield. The reaction tolerated several
substituted aryl groups, including the challenging preparation of
pyridyl-containing derivatives. A series of control experiments strongly
suggested that the new rearrangement involves a key isocyanate intermediate
and a further reaction with in situ-generated methylthiomethyl acetate.
The photophysical properties of some of the synthesized derivatives
as well as their use in live cell imaging were also investigated,
revealing that some of the substituted maleimides are capable of selectively
staining different regions of the cells.
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