A bioactive sprite: Recent advances in the application of vinyl sulfones in drug design and organic synthesis

Life Sciences, Journal Year: 2024, Volume and Issue: 352, P. 122904 - 122904

Published: July 9, 2024

Language: Английский

---

Vicinal Thiosulfonylation of ortho-(Alkynyl)benzyl Thiosulfonates/Sulfurothioates for Direct Synthesis of Sulfonyl-Derived Isothiochromenes

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(10), P. 3628 - 3638

Published: March 5, 2025

A new type of ortho-(alkynyl)benzyl thiosulfonates and sulfurothioates (Bunte salts) have been prepared for the first time to investigate vicinal thiosulfonylation. unique Au-catalyzed atom transfer radical cyclization (ATRC) ortho-alkynyl benzyl has successfully achieved, producing sulfonyl-derived isothiochromenes as a major product through favored 6-endo-dig cyclization. Additionally, thiosulfonylation Bunte salts with sodium sulfinates realized under influence Mn(OAc)3·2H2O afford 4-sulfonyl-isothiochromene derivatives exclusively. range were readily accessed in promising yields, including gram-scale reactions. Of note, postsynthetic transformations possible mechanistic insights uncovered.

Language: Английский

---

Synthesis of Adenine Nucleosides with a Reactive (β-Iodovinyl)sulfone or (β-Keto)sulfone Group at the C2 Position and Their Polymerase-Catalyzed Incorporation into DNA

Molecules, Journal Year: 2025, Volume and Issue: 30(6), P. 1358 - 1358

Published: March 18, 2025

Iodosulfonylation of an ethynyl group at the C2 position 2′-deoxyadenosine or adenosine with TsI provides (E)-2-(β-iodovinyl)sulfones. The latter undergo nucleophilic substitution amines via addition–elimination to give β-sulfonylvinylamines (enamines). Acid-catalyzed hydrolysis 2-(β-keto)sulfones, mechanistically different probes that react alkyl halides, resulting in α-alkylation. Adenine nucleosides a β-ketosulfone C2, during conversion their 5′-triphosphate form, unexpected 2-carboxylic acid nucleotides. 2′-deoxyadenosine-2-carboxylic was incorporated by human DNA polymerase into one-nucleotide gap substrate.

Language: Английский

---

Synthesis of Sulfonylthiophenes through [3+2] Cycloaddition of Pyridinium 1,4-Zwitterionic Thiolates with (E)-β-Iodovinyl Sulfones or Bromoallylsulfones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 7, 2025

A novel metal-free [3+2] cycloaddition strategy involving (E)-β-iodovinyl sulfones or bromoallylsulfones and pyridinium 1,4-zwitterionic thiolates for the efficient synthesis of sulfonylthiophenes is presented. This method exhibits good substrate tolerance, catalysis, easily prepared bench-stable substrates. The findings highlight a practical protocol accessing sulfonyl-substituted thiophenes with significant biological chemical relevance, serving as an alternative to traditional metal catalysis oxidation aryl/heteroaryl sulfides.

Language: Английский

---

Metal-free iodosulfonylation of alkynes to access (E)-β-iodovinyl sulfones in water

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We report a metal-free iodosulfonylation of alkynes in water at room temperature, which efficiently produces ( E )-β-iodovinyl sulfones good to excellent yields with high regio- and stereoselectivity.

Language: Английский

---