A visible light-mediated radical Smiles rearrangement has been achieved using neutral eosin Y as a direct hydrogen atom transfer (HAT) photocatalyst. Novel N-heterocycles as single diastereomers featuring an isothiazolidin-3-one 1,1-dioxide moiety are directly accessed by this method. A wide range of functional groups can be incorporated in the products by employing diverse aldehydes and N-(hetero)arylsulfonyl propiolamides. The transformation proceeds through a cascade of visible-light-induced HAT, 1,4-addition, Smiles rearrangement, 5-endo-trig cyclization and a reverse HAT process. Preliminary biological studies of the highly functionalized heterocyclic compounds suggest potential anti-cancer activity with some of the synthesized compounds.

中文翻译：

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中性伊红Y作为直接氢原子转移光催化剂促进的自由基微笑重排

使用中性伊红 Y 作为直接氢原子转移 (HAT) 光催化剂，已经实现了可见光介导的自由基微笑重排。通过这种方法可以直接获得作为具有异噻唑啉-3-one 1,1-二氧化物部分的单一非对映异构体的新型 N-杂环。通过使用不同的醛和 N-(杂)芳基磺酰基丙酰胺，可以在产品中加入多种官能团。转化通过一系列可见光诱导的 HAT、1,4-加法、Smiles 重排、5-endo-trig 环化和反向 HAT 过程进行。高度官能化杂环化合物的初步生物学研究表明，某些合成化合物具有潜在的抗癌活性。