Diverse 3‑Methylthio-4-Substituted Maleimides through a Novel Rearrangement Reaction: Synthesis and Selective Cell Imaging

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 ≤9...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 87; no. 5; pp. 2809 - 2820
Main Authors:	Meirelles, Luan V, de Castro, Pedro P, Passos, Saulo T. A, Carvalho, Bernardo B. P. P, Franco, Chris H. J, Correa, José R, Neto, Brenno A. D, Amarante, Giovanni W
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 04-03-2022
Subjects:	Maleimides
Online Access:	Get full text
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/acs.joc.1c02714