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I 2 -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.

Zhi-Cheng YuKai-Lu ZhengXi ShenYou ZhouXiang-Long ChenLi-Sheng WangYan-Dong WuYan-Dong Wu
Published in: Organic letters (2024)
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.
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