16766-62-4Relevant academic research and scientific papers
Redox-Divergent Construction of (Dihydro)thiophenes with DMSO
Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang
, p. 24284 - 24291 (2021/10/08)
Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.
Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
Habiger, Christoph,Haut, Franz-Lucas,Korber, Johannes Nepomuk,Müller, Thomas,Magauer, Thomas,Mayer, Peter,Speck, Klaus,Wurst, Klaus
supporting information, (2019/09/06)
Here we present a comprehensive study on the [3+2]-cycloaddition of thiocarbonyl ylides with a wide variety of alkenes and alkynes. The obtained dihydro- and tetrahydrothiophene products serve as exceptionally versatile intermediates providing access to thiophenes, dienes, dendralenes, and vic-quarternary carbon centers. The use of high-pressure conditions enables thermally unstable, sterically encumbered or moderately reactive substrates to undergo the cycloaddition under mild conditions, thereby increasing the yield by up to 58percent. In addition, we showcase its utility by the formal syntheses of the pharmaceuticals NGB 4420 and tenilapine.
Inhibition of Liver Alcohol Dehydrogenase and Ethanol Metabolism by 3-Substituted Thiolane 1-Oxides
Chadha, Vijay K.,Leidal, Kevin G.,Plapp, Bryce V.
, p. 36 - 40 (2007/10/02)
3-Substituted thiolane oxides (methyl, n-butyl, n-hexyl, and phenyl) were prepared and tested as inhibitors of horse, monkey, and rat liver alcohol dehydrogenases and of ethanol metabolism in rats.These compounds inhibit alcohol oxidation in an uncompetit
