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

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

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Sn(OTf)₂-Catalyzed (3 + 2) Cycloaddition/Sulfur Rearrangement Reaction of Donor–Acceptor Cyclopropanes with Indoline-2-thiones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1672 - 1676

Published: Feb. 15, 2024

The (3 + 2) cycloaddition/sulfur rearrangement reaction of donor–acceptor cyclopropanes bearing a single keto acceptor with indoline-2-thiones has been realized. Under the catalysis Sn(OTf)2, series functionalized 3-indolyl-4,5-dihydrothiophenes were synthesized moderate to excellent yields.

Language: Английский

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Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2784 - 2790

Published: April 23, 2024

Abstract Ytterbium triflate catalysed domino reaction of (3‐formyl‐4‐indolyl)‐derived donor‐acceptor cyclopropane with primary amines provides a simple approach to an unprecedented tetracyclic skeleton in which tropane system is peri ‐annulated indole core. This process involves the formation imine and its (3+2)‐cross‐cycloaddition moiety, yielding tropane‐fused core under mild conditions. These products are significant interest for pharmacology as potential hybrid molecules dual mode action.

Language: Английский

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Sulfur heterocycle synthesis from cyclopropanes (microreview)

Chemistry of Heterocyclic Compounds, Journal Year: 2025, Volume and Issue: unknown

Published: June 3, 2025

Language: Английский

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Yb(OTf)₃-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with Donor–Acceptor Cyclopropanes

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14587 - 14600

Published: Oct. 11, 2023

A Yb(OTf)3-catalyzed formal (4 + 3) cycloaddition reaction of donor-acceptor cyclopropanes with 3-benzylideneindoline-2-thiones as sulfur-containing 4π components has been successfully achieved. series functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized good yields and moderate to diastereoselectivity. The described herein represented the inaugural 3-benzylideneindoline-2-thiones.

Language: Английский

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Sc(OTf)3-catalyzed diastereoselective [4 + 2] cycloaddition reaction of 3-benzylideneindoline-2-thiones with alkylidene malonates

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 135, P. 154886 - 154886

Published: Dec. 13, 2023

Language: Английский

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

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

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