In(OTf)3-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with 2-Indolylmethanols DOI

Xuelong Wang,

Yi Yang, Yan Jiang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5902 - 5906

Published: Jan. 1, 2024

We report the In(OTf)

Language: Английский

Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor–Acceptor Cyclopropanes with Indoline-2-Thiones DOI

Chen-Ying Zhai,

Bing Zhao, Xuelong Wang

et al.

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

Published: Feb. 20, 2025

Lewis acid-enabled reactions of donor-acceptor cyclopropanes (DACs) with indoline-2-thiones are reported. The reaction exhibits tunable annulation depending on the acid and substituent at N1 indoline-2-thiones. With AlCl3 as 1-isopropylindoline-2-thiones reactants, a direct ring opening DACs, followed by intramolecular nucleophilic addition/dehydration takes place leading to formation dihydro-2H-thiepino[2,3-b]indoles in moderate good yields. Using Yb(OTf)3 promoter 1-unsubstituted (3 + 2) cycloaddition DACs accompanied sulfur rearrangement give 3-indolyl-4,5-dihydrothiophenes In addition, synthetic transformation 3-indolyl-4,5-dihydrothiophene sulfone indole-based axially chiral scaffolds further extends utility structural complexity.

Language: Английский

Citations

1
Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art DOI Creative Commons
Giulia Antonini, Laura Petrosilli,

Ilaria Giussani

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(39)

Published: Aug. 10, 2024

Abstract The intricate nature of carbohydrate structures has prompted the scientific community to seek efficient protocols for their manipulation. Lengthy synthetic pathways, often necessary achieve complex sugar structures, pose challenges not only in terms time and cost but also regarding environmental sustainability. Consequently, domino transformations serve as valuable tools streamlining drug discovery processes. Sequential procedures involving fewer steps minimal isolation/purification are particularly appealing organic chemists field chemistry. This review highlights several examples applied carbohydrates, aiming summarize chemical potential delivering sugar‐based compounds with significant applications generation new scaffolds biology.

Language: Английский

Citations

1
Catalytic ring-strain release toward a facial and efficient synthesis of versatile C-glycosides DOI
Y. Zhang,

Xiao-Lin Zhang,

Han Ding

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110560 - 110560

Published: Oct. 1, 2024

Language: Английский

Citations

1
In(OTf)3-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with 2-Indolylmethanols DOI

Xuelong Wang,

Yi Yang, Yan Jiang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5902 - 5906

Published: Jan. 1, 2024

We report the In(OTf)

Language: Английский

Citations

0