Organocatalytic Deoxygenative [3+2] Cycloaddition of N-Hydroxyamides with Alkynes to Access Isoxazoles DOI
Haixiang Wang, Yan Sun,

Wentong Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

Although the transition-metal-catalyzed [3+2] cycloadditions to access isoxazoles have been described well, organocatalytic methods remain underdeveloped. Herein, we report use of an organophosphine catalyst for preparation a series with exceptional regioselectivity via cycloaddition

Language: Английский

Skeletal Editing of Isatins for Heterocycle Molecular Diversity DOI
Tiantian Zhang, Huangdi Feng

The Chemical Record, Journal Year: 2024, Volume and Issue: 24(6)

Published: June 1, 2024

Isatins have been widely used in the preparation of a variety heterocyclic compounds, where skeletal editing isatins has shown significant advantages for construction diverse heterocycles. This review highlights progress made last decade (2013-2023) isatin scaffold. A series ring expansion reactions quinoline skeleton, quinolone polycyclic quinazoline medium-sized as well opening generation 2-(azoly)aniline skeleton by cleavage C-C bond and C-N are highlighted. It is hoped that this will provide some understanding chemical transformations contribute to further realization its molecular diversity.

Language: Английский

Citations

5
Sequence [2,3]‐Sigmatropic Rearrangement: One‐Pot Synthesis of Propargyl Allenylamines DOI
Huihui Feng,

Yujuan Xie,

Liliang Huang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(18), P. 2223 - 2227

Published: May 14, 2024

Comprehensive Summary Allenes, served as highly sought‐after building blocks, are an indispensable component of synthetic chemistry. Their utility in modulating the chemical, physical, and pharmaceutical properties organic compounds make allenes a desirable choice various applications. Here, we report facile method for atom‐economical synthesis propargyl allenylamines via underdeveloped [2,3]‐sigmatropic rearrangement. Our strategy employs easily accessible propargylamines starting materials, which first converted into ammonium salts, followed by base‐promoted This one‐pot, two‐step reaction proceeds absence transition metals, displays very broad scope, does not require introduction electron‐withdrawing group materials.

Language: Английский

Citations

4
Synthesis of Tetrasubstituted Pyrroles via DBU-Mediated Cyclization of Unactivated Propargyl Tertiary Amines DOI
Pengyu Zhou, Tiantian Zhang, Q. Richard Lu

et al.

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

Published: March 10, 2025

Compared with the well-developed cyclization of functionalized propargylamines, use unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted via a DBU-mediated intramolecular cycloaddition N-alkyl propargylamines. This reaction employs dihydropyrrole intermediates, followed by oxidation produce in presence 2,3-dichloro-5,6-dicyano-p-benzoquinone. In addition, broad substrate scope, high atom economy, selectivity, and simple operation are also advantages this protocol.

Language: Английский

Citations

0
Amine-catalyzed metal-free deamination of propargylamines with water toward chalcones DOI
Pengyu Zhou, Liliang Huang,

Yujuan Xie

et al.

Molecular Catalysis, Journal Year: 2022, Volume and Issue: 534, P. 112808 - 112808

Published: Nov. 18, 2022

Language: Английский

Citations

9
Synthesis of oxazolines through a Pd-catalyzed alkyne-enabled C N activation of oxazolidines DOI

Ling Zhong,

Ruidan Shi,

Liliang Huang

et al.

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 134, P. 154882 - 154882

Published: Dec. 9, 2023

Language: Английский

Citations

5
Metal- and oxidant-free skeletal reorganizing of oxazolidines to access N-Vinylpyrroles DOI

Ruidan Shi,

Xianjun Xu,

Ling Zhong

et al.

Sustainable Chemistry and Pharmacy, Journal Year: 2024, Volume and Issue: 42, P. 101768 - 101768

Published: Sept. 17, 2024

Language: Английский

Citations

1
An asymmetric metal-templated route to amino acids with an isoquinolone core via a Rh(iii)-catalyzed coupling of aryl hydroxamates with chiral propargylglycine Ni(ii) complexes DOI
Mikhail A. Arsenov,

Nadezhda V. Stoletova,

Tat’yana F. Savel’yeva

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(47), P. 9385 - 9391

Published: Jan. 1, 2022

The first asymmetric route to artificial amino acids with an isoquinolone skeleton was elaborated via a straightforward Rh( iii )-catalyzed C–H activation/annulation reaction.

Language: Английский

Citations

4
Synthesis ofN-alkenylisoquinolinonesviapalladium-catalyzed cyclization/C4–O bond cleavage of oxazolidines DOI

Xianjun Xu,

Liliang Huang,

Eva Smits

et al.

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(44), P. 21176 - 21180

Published: Jan. 1, 2022

A palladium-catalyzed cascade ring-opening reaction to synthesize N -alkenylisoquinolinones via cyclization and C–O bond cleavage is reported.

Language: Английский

Citations

4
Organocatalytic Deoxygenative [3+2] Cycloaddition of N-Hydroxyamides with Alkynes to Access Isoxazoles DOI
Haixiang Wang, Yan Sun,

Wentong Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

Although the transition-metal-catalyzed [3+2] cycloadditions to access isoxazoles have been described well, organocatalytic methods remain underdeveloped. Herein, we report use of an organophosphine catalyst for preparation a series with exceptional regioselectivity via cycloaddition

Language: Английский

Citations

0