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

Ka Key Cheung,

Ran Lin

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(36)

Опубликована: Июль 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.

Язык: 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

и другие.

Synthetic Communications, Год журнала: 2025, Номер unknown, С. 1 - 12

Опубликована: Апрель 26, 2025

Язык: Английский

Процитировано

0

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

и другие.

Synthetic Communications, Год журнала: 2024, Номер 54(4), С. 312 - 320

Опубликована: Янв. 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.

Язык: Английский

Процитировано

2

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

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(42)

Опубликована: Сен. 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.

Язык: Английский

Процитировано

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(9), С. 1413 - 1418

Опубликована: Апрель 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

Язык: Английский

Процитировано

5

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

Ka Key Cheung,

Ran Lin

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(36)

Опубликована: Июль 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.

Язык: Английский

Процитировано

5

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

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2225 - 2233

Опубликована: Сен. 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.

Язык: Английский

Процитировано

1

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

Liangliang Li

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 10(3), С. 686 - 698

Опубликована: Дек. 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.

Язык: Английский

Процитировано

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

и другие.

Green Chemistry, Год журнала: 2022, Номер 24(24), С. 9690 - 9696

Опубликована: Янв. 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.

Язык: Английский

Процитировано

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

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2655 - 2667

Опубликована: Окт. 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.

Язык: Английский

Процитировано

0

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

Ka Key Cheung,

Ran Lin

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(36)

Опубликована: Июль 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.

Язык: Английский

Процитировано

0