TFA-Catalyzed cascade annulation of thioamides with aromatic hydrazides/amines: an internal oxidant-triggered protocol to diverse N-heterocycles DOI Creative Commons
Wujiu Jiang, Yuxing Tan, Penghui Ni

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Language: Английский

Phosphine‐Catalyzed Divergent γ,γ‐ and ε,γ‐Umpolung Domino Additions of Bisoxindoles with Allenoates: Construction of Vicinal All‐Carbon Quaternary Stereocenters and Formal Total Synthesis of Dimeric Cyclotryptamine Alkaloids DOI Open Access
Yufei Zhang, Jing Chen, Hui Yao

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 25, 2025

Comprehensive Summary Vicinal all‐carbon quaternary stereocenters are widely present in natural products and bioactive molecules. However, the construction of such motif one step from readily available starting materials remains a significant challenge. Herein, we report phosphine‐catalyzed divergent γ,γ‐ ε,γ‐umpolung domino addition bisoxindoles with allenoates. This method serves as practical tool for concise synthesis series bisoxindole derivatives bearing sterically hindered vicinal under mild reaction conditions. The applicability this novel was demonstrated gram‐scale three known advanced intermediates total syntheses calycanthine, chimonanthine folicanthine.

Language: Английский

Citations

2

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization DOI
Zhengyang Chen, Dan Xiong, Nengzhong Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2762 - 2767

Published: Jan. 1, 2024

A P(NMe2)3-catalyzed [4 + 2] annulation of 2-amino-β-nitrostyrenes and β′-acetoxy allenoates followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization has been developed.

Language: Английский

Citations

9

Facile synthesis of 2-vinylindolines via a phosphine-mediated α-umpolung/Wittig olefination/cyclization cascade process DOI

Shu‐Hui Li,

Dan Xu,

Hui Yao

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(53), P. 6773 - 6776

Published: Jan. 1, 2024

A novel phosphine-mediated α-umpolung/Wittig olefination/cyclization cascade process between o -aminobenzaldehydes and Morita–Baylis–Hillman (MBH) carbonates has been ingeniously developed for the facile synthesis of a broad range 2-vinylindolines.

Language: Английский

Citations

6

Pyridine-Catalyzed Chemoselective Four-Component Cascade Reaction of Aromatic Aldehydes, Malononitrile/Cyanoacetates, MBH Carbonates, and Alcohols DOI
Boning Li,

Xianfei Hu,

Hui Yao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7576 - 7583

Published: Sept. 3, 2024

An efficient pyridine-catalyzed chemoselective four-component cascade reaction of aromatic aldehydes, malononitrile/cyanoacetates, Morita-Baylis-Hillman (MBH) carbonates, and alcohols has been established. This one-pot progressed in an unusual with solvent participation via a Knoevenagel condensation/oxa-Michael addition/S

Language: Английский

Citations

2

Controllable Phosphine-Catalyzed Three-Component Domino Reaction of Activated Alkenes with Morita–Baylis–Hillman (MBH) Carbonates: Divergent Synthesis of Densely Functionalized Cyclopentanes and Diquinanes DOI

Yi Li,

Xianfei Hu,

Boning Li

et al.

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

Published: Dec. 7, 2024

An unexpected phosphine-catalyzed controllable three-component domino reaction involving [1 + 2 2] annulation and 2]/[3 sequential of 2-arylmethylidene cyanoacetates/malononitriles with Morita-Baylis-Hillman (MBH) carbonates has been developed. A broad range densely functionalized cyclopentanes diquinanes bearing five or four consecutive stereogenic centers, including two all-carbon quaternary stereocenters, were smoothly acquired in moderate to excellent yields under mild conditions from readily available materials. Moreover, this divergent transformation enables the simultaneous generation three new C-C bonds one carbocyclic rings only step.

Language: Английский

Citations

2

Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates DOI

Mengting Tan,

Yunping Zheng, Sen Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9203 - 9209

Published: Oct. 21, 2024

Controlling the selectivity of reactions is a significantly attractive strategy in synthetic organic chemistry. Herein, an efficient base-controlled chemodivergent domino reaction between o-aminochalcones and γ-bromocrotonates has been developed. A series cis-2,3-disubstituted indolines cyclopropane-fused tetrahydroquinolines were obtained via two pathways with broad substrate scope moderate to excellent yields under transition-metal-free conditions. It noteworthy that could be used as C1 or C2 synthons by modulating base; particular, both nucleophiles electrophiles generate cyclopropanes for first time.

Language: Английский

Citations

1

An efficient one-step synthesis of a new series of mutifunctional olefins and direct hydroxymethylation of α-substituted β-keto esters DOI
Olfa Mhasni, Julien Legros, Farhat Rezgui

et al.

Synthetic Communications, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 12

Published: Sept. 13, 2024

Language: Английский

Citations

0

Bioactive Molecules from Lignocellulose‐derived Platform Chemicals DOI

Guorui Qiang,

Mohd Farhan Ansari,

Zhuohua Sun

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(23), P. 4805 - 4834

Published: Oct. 21, 2024

Abstract The ever‐increasing prevalence of diseases and inadequate resources on Earth are threats to society. Biomass is an abundant resource, bioactive compounds produced from biomass environmentally benign in contrast conventional chemical synthesis methods, which frequently depend non‐renewable resources. In addition, the functionalized monomers allow atom economical molecules. This review aims provide insight into molecules lignocellulose‐derived platform chemicals. Existing methodology catalytic systems summarized for targeted cellulose, hemicellulose, lignin‐derived biological activities obtained biomass, such as antioxidant, anti‐inflammatory, anticancer properties, discussed.

Language: Английский

Citations

0

Base mediated aza-[2 + 1] annulation and regioselective aziridine ring-opening cascade: mild synthesis of functionalized β-amino ketones from cyclic N-sulfonyl aldimines and α-carbonyl sulfonium salts DOI Creative Commons

Xiaoqiang Lei,

Yanyan Sun,

Qing‐Lan Guo

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(24), P. 17178 - 17183

Published: Jan. 1, 2024

Cyclic N-sulfonyl aldimines are well-known aza-[2C]-synthons for various [2 + n] annulation reactions. Herein we describe a novel base mediated 1] and regioselective aziridine ring-opening reaction cascade, which provides an efficient distinct synthetic strategy from readily available cyclic α-carbonyl sulfonium salts leading to β-amino ketone derivatives through the corresponding fused tri-substituted aziridines. This one-pot, two-step process involves formation of C-C C-N bonds subsequent cleavage bond. The features developed include use mild conditions, broad substrate scope, excellent yields. utility this approach was demonstrated by gram-scale operation further product derivatizations.

Language: Английский

Citations

0

TFA-Catalyzed cascade annulation of thioamides with aromatic hydrazides/amines: an internal oxidant-triggered protocol to diverse N-heterocycles DOI Creative Commons
Wujiu Jiang, Yuxing Tan, Penghui Ni

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Language: Английский

Citations

0