I2-Induced Umpolung: Synthesis of a 1,6-Dihydrofuro[3,2-b]pyrazolo[3,4-e][1,4]thiazine Skeleton via an Unconventional 1,4-Dithiane-2,5-diol Reaction Mode,Organic Letters

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I2-Induced Umpolung: Synthesis of a 1,6-Dihydrofuro[3,2-b]pyrazolo[3,4-e][1,4]thiazine Skeleton via an Unconventional 1,4-Dithiane-2,5-diol Reaction Mode
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-06 , DOI: 10.1021/acs.orglett.4c02813
Zhi-Cheng Yu ₁ , Kai-Lu Zheng ₂ , Xi Shen ₁ , You Zhou ₁ , Xiang-Long Chen ₁ , Li-Sheng Wang ₁ , Yan-Dong Wu ₁ , An-Xin Wu _{1,

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Affiliation

In this paper, novel sulfur-containing 1,6-dihydrofuro[3,2-b]pyrazolo[3,4-e][1,4]thiazine skeletons were constructed from the simple and readily available materials enaminone, 5-aminopyrazole, and 1,4-dithiane-2,5-diol. Furthermore, a novel 1,4-dithiane-2,5-diol reaction mode has been developed through a double-dipole-reversal process induced by iodine that results in the formation of six new bonds and two new rings in a one-pot reaction. This method shows good substrate compatibility, and the products can be further modified with a variety of pharmaceuticals. Additionally, this novel skeleton exhibits good fluorescence properties in solution, enabling bright and stable green fluorescence imaging in HeLa cells.

中文翻译：

I2 诱导的 Umpolung：通过非常规 1,4-二噻烷-2,5-二醇反应合成 1,6-二氢呋喃[3,2-b]吡唑并[3,4-e][1,4]噻嗪骨架模式

本文以简单易得的材料烯胺酮、5-氨基吡唑、和1,4-二噻烷-2,5-二醇。此外，通过碘诱导的双偶极反转过程开发了一种新的1,4-二噻烷-2,5-二醇反应模式，在一锅反应中形成六个新键和两个新环。该方法表现出良好的底物相容性，产品可与多种药物进一步修饰。此外，这种新颖的骨架在溶液中表现出良好的荧光特性，能够在 HeLa 细胞中实现明亮且稳定的绿色荧光成像。

更新日期：2024-09-06

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