Sc(Otf)3-Catalyzed Diastereoselective [4 + 2] Cycloaddition Reaction of 3-Benzylideneindoline-2-Thiones with Alkylidene Malonates DOI
Yan Jiang, Xuelong Wang, Junyi Zeng

et al.

Published: Jan. 1, 2023

A Sc(OTf)3-catalyzed diastereoselective [4 + 2] cycloaddition reaction of 3-benzylideneindoline-2-thiones with 2-alkylidene malonates has been realized, leading to biologically important indole-annulated thiopyran derivatives in moderate good yields. Moreover, a gram-scale and chemical transformation the cycloadduct sulfone were carried out further extend synthetic utility.

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

Sergey M. Antropov,

Sofiya A. Tokmacheva,

Ирина И. Левина

et al.

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

Citations

5
(3+2) Annulation of Donor–Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds DOI
Neeraj Yadav, Prabal Banerjee

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

Published: March 27, 2025

Herein, we present an acid- and base-mediated approach for ring opening of donor-acceptor cyclopropanes (DACs) followed by (3+2) annulation, yielding biologically relevant gem-difluorinated cyclopentenes via α,α-difluoroketone scaffolds. Fluorinated rings are essential building blocks in drug discovery materials research. This methodology has a broad substrate scope, is scalable, provides practical synthetic route to obtain value-added fluorinated compounds.

Language: Английский

Citations

0
Strain-Releasing Hydrogenation of Donor–Acceptor Cyclopropanes and Cyclobutanes via Electrochemical Site Selective Carbonyl Reduction DOI

Nakshatra Banerjee,

Rakesh Kumar,

Biswadeep Manna

et al.

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

Published: April 21, 2025

An acid or hydrogen gas-free electrochemical protocol is established for the hydrogenation of strained rings (cyclopropane and cyclobutane) at room temperature atmospheric pressure. The mechanistic study revealed that reaction was initiated via reduction carbonyl group. methodology highly specific toward such as cyclopropane cyclobutane, which exhibit broad functional group tolerance.

Language: Английский

Citations

0
Cyclization reactions of cyclopropane derivatives with conjugated carbo- and heterosystems DOI
Pavel G. Sergeev, Роман А. Новиков, Yury V. Tomilov

et al.

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(3), P. RCR5111 - RCR5111

Published: March 1, 2024

The strained structure of cyclopropanes serves as a kind trigger for variety chemical transformations. Among others, processes involving conjugated unsaturated systems are particular interest. bonds characterized by the possibility flexibly varying their reactivity up to full involvement in This review is first consider options implementing idea combining strain energy and synthetic capacity within single concept. A detailed analysis activated numerous carbodiene heterodiene presented.<br> bibliography includes 289 references.

Language: Английский

Citations

1
Sc(OTf)3-catalyzed diastereoselective [4 + 2] cycloaddition reaction of 3-benzylideneindoline-2-thiones with alkylidene malonates DOI
Xuelong Wang, Junyi Zeng, Yi Yang

et al.

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

Published: Dec. 13, 2023

Language: Английский

Citations

2
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
Sc(Otf)3-Catalyzed Diastereoselective [4 + 2] Cycloaddition Reaction of 3-Benzylideneindoline-2-Thiones with Alkylidene Malonates DOI
Yan Jiang, Xuelong Wang, Junyi Zeng

et al.

Published: Jan. 1, 2023

A Sc(OTf)3-catalyzed diastereoselective [4 + 2] cycloaddition reaction of 3-benzylideneindoline-2-thiones with 2-alkylidene malonates has been realized, leading to biologically important indole-annulated thiopyran derivatives in moderate good yields. Moreover, a gram-scale and chemical transformation the cycloadduct sulfone were carried out further extend synthetic utility.

Language: Английский

Citations

0