Palladium-Catalyzed [3+2] Cycloaddition of 4-Vinyl-4-Butyro-lactones with Sulfamate-Derived Cyclic Imines: Construction of Sulfamate-Fused Pyrrolidines DOI
Honghao Sun,

Siyuan Ding,

Bo Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The palladium-catalyzed [3 + 2] decarboxylative cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines has been developed, providing the sulfamate-fused pyrrolidine derivatives in high yields good diastereoselectivities.

Language: Английский

Studies on the [4 + 2] cycloaddition and allylic substitution of indole-fused zwitterionic π-allylpalladium DOI
Zhengyu Han, Yu Xue, Xiang Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(40), P. 8162 - 8169

Published: Jan. 1, 2023

The zwitterionic π-allylpalladium species, also known as dipoles, are important synthons widely used in various reactions including cycloaddition and allylic substitution. This study reported the development of a new indole-fused precursor compound its application [4 + 2] substitution reactions. As result, synthesis pyrrolo[3,2,1-ij]quinazolin-3-one 7-vinyl indole compounds was achieved with moderate to good yields. Notably, reaction exhibited excellent regio- stereoselectivity.

Language: Английский

Citations

5
Palladium-Catalyzed (4 + 1) Annulation of 4-Vinylbenzodioxinones with Sulfur Ylides: Diastereoselective Synthesis of Dihydrobenzofuran Derivatives DOI
Yi Tang, Xiaojing Sun,

Yu Tan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8951 - 8959

Published: May 30, 2024

Palladium-catalyzed (4 + 1) annulation of 4-vinylbenzodioxinones with sulfur ylides has been developed to afford various dihydrobenzofuran derivatives in moderate high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating application potential current organic synthesis.

Language: Английский

Citations

1
Palladium-Catalyzed [3 + 2] Cycloaddition of 4-Vinyl-4-Butyrolactones with Alkenes: Synthesis of Spirocyclopentane Compounds DOI
Honghao Sun,

A.‐T. SONG,

Shuang Gu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

A palladium-catalyzed [3 + 2] cycloaddition of 4-vinyl-4-butyrolactones (VBLs) with alkenes has been developed to afford various spirocyclopentane products in high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating potential application current organic synthesis.

Language: Английский

Citations

1
Sequential Dearomatization/Rearrangement of Quinazoline-Derived Azomethine Imines for the Synthesis of Nitrogen-Rich Three-Dimensional Cage-Like Molecules DOI
Yujiao Wang,

Chunguang Yang,

Shuang Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3557 - 3562

Published: April 23, 2024

A sequential dearomatization/rearrangement reaction between quinazoline-derived azomethine imines and crotonate sulfonium salts has been developed to provide a series of three-dimensional cage-like molecules. The involves two dearomatizations, cyclizations, C-C bond three C-N formations in one step. new transformation broad substrate scope, does not require any added reagents, proceeds under room temperature short time. mechanistic rationale for the is also presented. Furthermore, synthetic compounds are evaluated their glucose control effect. Compounds

Language: Английский

Citations

1
Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp2)–H functionalization DOI
Neeraj Kumar Mishra, Amitava Rakshit,

Kyeongwon Moon

et al.

Bulletin of the Korean Chemical Society, Journal Year: 2023, Volume and Issue: 45(2), P. 131 - 144

Published: Dec. 12, 2023

Abstract The synthesis and functionalization of privileged nitrogen heterocycles has emerged as a central topic in drug discovery material science. In this context, the tandem C–H intramolecular annulation received prodigious attention, it is able to expedite construction heteroaromatic frameworks beyond conventional functionalization. general, significant effort been made develop [3 + 2] dipolar cycloaddition azomethine imines with π‐unsaturated compounds. Moreover, 3], [4 2 2], [5 3] reactions various dipolarophiles have demonstrated. To date, however, combination catalytic cyclization using both directing groups units less explored. This review focuses on recent progress toward azomethines range coupling partners.

Language: Английский

Citations

2
Synthesis of Angular Polycyclic Aromatic Molecules Via Pd‐Catalyzed Decarboxylative Cycloaddition of 2‐Alkylidenetrimethylene Carbonates with Quinazoline‐Derived Azomethine Imines DOI Open Access

Bo Yang,

Jin‐Qi Wang,

Li‐Ming Zhao

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(31)

Published: Aug. 14, 2024

Abstract A formal [4+3] cycloaddition of 2‐alkylidenetrimethylene carbonates with quinazoline‐derived azomethine imines is described. Under Pd catalysis, the reaction works efficiently under room temperature to afford angular quinazoline‐fused seven‐membered N,N,O ‐heterocycles. variety cyclic and were well tolerated mild conditions. This work demonstrates synthetic utility decarboxylative cycloadditions for synthesis polycyclic aromatic molecules.

Language: Английский

Citations

0
Pd-Catalyzed Sequential Intramolecular Annulation/ Intermolecular [3+2] Cycloaddition of 5-Allenyloxazolidine-2,4-diones with Dipoles: Synthesis of Spiroheterocycles DOI
Yujie Dong, Jun Liu,

Rongjin Ning

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(76), P. 10516 - 10519

Published: Jan. 1, 2024

Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile

Language: Английский

Citations

0
Quinazoline-Derived Azomethine Imines as Substrates To Access Polycyclic Compounds DOI
Li‐Ming Zhao, Yujiao Wang

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15393 - 15403

Published: Oct. 22, 2024

Quinazolines are essential structural constituents of many pharmaceuticals and bioactive natural products. Quinazoline-derived azomethine imines (QAIs) have emerged recently as valuable building blocks for the synthesis various quinazoline derivatives. This Synopsis presents recent advances in (formal) cycloaddition reactions QAIs quinazoline-fused 5- to 8-membered heterocycles well three-dimensional compounds.

Language: Английский

Citations

0
Palladium-Catalyzed [3+2] Cycloaddition of 4-Vinyl-4-Butyro-lactones with Sulfamate-Derived Cyclic Imines: Construction of Sulfamate-Fused Pyrrolidines DOI
Honghao Sun,

Siyuan Ding,

Bo Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The palladium-catalyzed [3 + 2] decarboxylative cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines has been developed, providing the sulfamate-fused pyrrolidine derivatives in high yields good diastereoselectivities.

Language: Английский

Citations

0