[2+2+1+1] Cycloaddition for de novo Synthesis of Densely Functionalized Phenols DOI
Wei Wei,

Ka Key Cheung,

Ran Lin

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(36)

Published: July 10, 2023

Abstract A unique benzannulation strategy for regioselective de novo synthesis of densely functionalized phenols is described. Through metal‐mediated formal [2+2+1+1] cycloaddition two different alkynes and molecules CO, a series were obtained. The allows efficient installation up to five substituents on phenol ring. resulting have substitution pattern from those obtained Dötz Danheiser benzannulations.

Language: Английский

Tandem [4C + 2C] cyclization reaction of α-acetyl-α-oxo ketene dithioacetals and acrylonitrile: A straightforward synthesis of polysubstituted cyclohex-3-enones DOI
Xiao-Bo Zhao,

Zixuan Cha,

Xinyue Liu

et al.

Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 12

Published: April 26, 2025

Language: Английский

Citations

0
NaOH promoted hydrolysis of α-oxo ketene- N, S -acetals: Effective synthesis of β-keto amides DOI
Liangliang Li, Chunxu Jiang, Tingting Peng

et al.

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(4), P. 312 - 320

Published: Jan. 2, 2024

An effective and novel synthesis of β-keto amides had been developed by NaOH promoted hydrolysis α-oxo ketene-N, S-acetals. It was found that the S-acetals in presence 2 equivalent refluxing EtOH (95%) gave excellent yields. The uses toxic harmful amines as well prepurification these nucleophilic reagents were not required reaction. method can extend to gram scale.

Language: Английский

Citations

2
Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates DOI
Saumitra Sengupta, Srihari Pabbaraja, Goverdhan Mehta

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(42)

Published: Sept. 5, 2022

Abstract Recursive Anionic Cyclization (RAC) continues to proliferate as a mechanistically distinct domino strategy. Deployment of nitroalkanes source recursive carbanions has created niche operating space for generating molecular complexity and diversity. This new corollary i. e. nitronate cyclization is the basis [5 C+1 C] strategy wherein act one‐carbon lynchpin, providing rapid access topologically intriguing, densely functionalized carbo‐ heterocycles embodying multiple chiral centers with regio‐, stereo‐ enantioselectivity. Extension aromatic domains, particularly via benzannulation reactions, further consolidated space. While leveraging functional versatility nitro group post‐domino modifications, such endeavors have culminated in total synthesis diverse natural products. An incisive analysis cyclizations their emergent potentials delineated this review. It hoped that focused narrative will enthuse draw practitioners arena advance field.

Language: Английский

Citations

10
HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones DOI

Daokai Xiong,

Zhengjie Zhang, Jing Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1413 - 1418

Published: April 12, 2023

Abstract Hexafluoroisopropanol (HFIP) has been extensively applied in organic synthesis as a versatile reaction media. However, the application of HFIP an catalyst rarely studied. Presented here, is example HFIP‐catalyzed Mannich‐type between quinoxalin‐2(1 H )‐ones and difluoroenoxysilanes. The developed protocol tolerates various substituents under mild conditions, providing divergent approach to construction difluoro‐substituted 3,4‐dihydroquinoxalin‐2(1 monofluoroquinoxalin‐2(1 51–92% yields. magnified image

Language: Английский

Citations

5
[2+2+1+1] Cycloaddition for de novo Synthesis of Densely Functionalized Phenols DOI Open Access
Wei Wei,

Ka Key Cheung,

Ran Lin

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(36)

Published: July 10, 2023

A unique benzannulation strategy for regioselective de novo synthesis of densely functionalized phenols is described. Through metal-mediated formal [2+2+1+1] cycloaddition two different alkynes and molecules CO, a series were obtained. The allows efficient installation up to five substituents on phenol ring. resulting have substitution pattern from those obtained Dötz Danheiser benzannulations.

Language: Английский

Citations

4
Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides DOI Creative Commons
Haifeng Yu, Wanting Zhang, Xuejing Cui

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2225 - 2233

Published: Sept. 3, 2024

An eco-friendly selective hydrolysis of chain α-oxo ketene N , S -acetals in water for the switchable synthesis β-keto thioesters and amides is reported. In refluxing water, reactions presence 1.0 equiv dodecylbenzenesulfonic acid effectively afforded excellent yield, while were successfully obtained yield when carried out 3.0 NaOH. The green approach to avoids use harmful organic solvents, thiols thiolacetates as well amines, which could result serious environmental safety issues.

Language: Английский

Citations

1
K2CO3-accelerated amidation of carboxylic acids using α-oxo ketene-N,S-acetals as amine surrogates DOI
Haifeng Yu, Xue Zhang,

Liangliang Li

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(3), P. 686 - 698

Published: Dec. 7, 2022

A novel and efficient K 2 CO 3 -accelerated amidation of carboxylic acids with α-oxo ketene- N , S -acetals as amine surrogates is developed.

Language: Английский

Citations

3
Catalyst- and additive-free [3 + 3] cyclization–aromatization of β,γ-dioxobutanoate with amines for synthesis ofp-aminophenols DOI
Hang Qian,

Cui-Cui Wang,

Zi-Chen Shen

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(24), P. 9690 - 9696

Published: Jan. 1, 2022

A [3 + 3] cyclization–aromatization of β,γ-dioxobutanoate with amines for synthesis p -aminophenols under catalyst- and additive-free conditions was developed. The reaction displays high efficiency in the late-stage modification drug molecules.

Language: Английский

Citations

3
Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones DOI Creative Commons

Bhaskar B. Dhotare,

Seema V. Kanojia,

Chahna K Sakhiya

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2655 - 2667

Published: Oct. 21, 2024

A transition-metal-free decarbonylation–oxidation protocol for the conversion of 3-arylbenzofuran-2(3 H )-ones to 2-hydroxybenzophenones under mild conditions has been developed. NMR studies confirmed role in-situ-generated hydroperoxide in conversion. The was applied a diverse range substrates access target products good excellent yields. structure–activity study 5-substituted-2-hydroxybenzophenones towards UV-protection abilities verified by mathematical calculations.

Language: Английский

Citations

0
[2+2+1+1] Cycloaddition for de novo Synthesis of Densely Functionalized Phenols DOI
Wei Wei,

Ka Key Cheung,

Ran Lin

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(36)

Published: July 10, 2023

Abstract A unique benzannulation strategy for regioselective de novo synthesis of densely functionalized phenols is described. Through metal‐mediated formal [2+2+1+1] cycloaddition two different alkynes and molecules CO, a series were obtained. The allows efficient installation up to five substituents on phenol ring. resulting have substitution pattern from those obtained Dötz Danheiser benzannulations.

Language: Английский

Citations

0