Base-Catalyzed Chalcogenative Annulation of N-Maleimido O-Aminobenzyl Alcohol with Elemental Sulfur/Selenium: Access to 1,4-Sulfa-/Selena-zepanes DOI

Yuanmin Wen,

Teng Liu,

Shuntao Huang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

We reported an unprecedented chalcogen element (Se, S) insertion reaction with functionalized aminomaleimide to assemble medium-sized nitrogen-containing organic selenium/sulfur catalyzed by bases. During these [5/6 + 1] tandem annulations, a variety of low-valent inorganic chalcogenides exhibited excellent compatibility, providing wide scope structurally diverse 1,4-selenazepanes (17 examples, 60–71% yields), 1,4-benzothiazepines (20 74–86% and 1,4-thiazines (6 31–68% yields). The characteristics this transformation are high atomic economy, formation two C–Se or C–S bonds in one step, avoiding the use unstable toxic reagents under mild conditions.

Language: Английский

Iron(III)-Mediated Nucleophilic Cascade Cyclization of Tertiary Enamides with Diselenides for the Construction of 3-Seleno-2-pyridones DOI
Xin‐Ming Xu, Jiping Wang, Xiaoxu Chen

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 12, 2025

An iron(III)-mediated nucleophilic cascade cyclization of N-propiolyl enamides with various diselenides was developed, which provides an efficient way to construct seleno-heterocycles. A mechanism study shows that the process involves selective addition C≡C bond generating a seleniranium ion, followed by intramolecular attack enaminic carbon tertiary enamide. Utilizing this protocol, variety 3-seleno-2-pyridones were successfully synthesized featuring good functional group compatibility and simple operation.

Language: Английский

Citations

1
Base-Catalyzed Chalcogenative Annulation of N-Maleimido O-Aminobenzyl Alcohol with Elemental Sulfur/Selenium: Access to 1,4-Sulfa-/Selena-zepanes DOI

Yuanmin Wen,

Teng Liu,

Shuntao Huang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

We reported an unprecedented chalcogen element (Se, S) insertion reaction with functionalized aminomaleimide to assemble medium-sized nitrogen-containing organic selenium/sulfur catalyzed by bases. During these [5/6 + 1] tandem annulations, a variety of low-valent inorganic chalcogenides exhibited excellent compatibility, providing wide scope structurally diverse 1,4-selenazepanes (17 examples, 60–71% yields), 1,4-benzothiazepines (20 74–86% and 1,4-thiazines (6 31–68% yields). The characteristics this transformation are high atomic economy, formation two C–Se or C–S bonds in one step, avoiding the use unstable toxic reagents under mild conditions.

Language: Английский

Citations

0