Synthesis of 2-Amino-3-Formylated Chromones via Pd Domino Catalysis DOI

Synfacts, Journal Year: 2023, Volume and Issue: 19(12), P. 1226 - 1226

Published: Nov. 15, 2023

Key words palladium catalysis - heterocycles skeletal editing domino

Language: Английский

Divergent Synthesis of 2-Chromonyl-3-hydrazono-chromones and 2-Alkoxy-3-hydrazono-chromones through Switchable Annulation Reactions of o-Hydroxyphenylenaminones with Aryldiazonium Salts DOI
Siyu Song,

Menglin Peng,

Zhilai Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 4980 - 4985

Published: June 4, 2024

An unprecedented selective chromone annulation reaction controlled by solvent for the divergent synthesis of two types 2,3-disubstituted skeletons has been developed. A variety 2-chromonyl-3-hydrazono-chromones and 2-alkoxy-3-hydrazono-chromones were constructed efficiently from readily available

Language: Английский

Citations

9
Controllable Synthesis of N-Heterocycles via Hydride Transfer Strategy-Enabled Formal [5 + 1] and [5 + 2] Cyclizations DOI
Ying Dong, Fangzhi Hu,

Huixin Wu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 332 - 337

Published: Dec. 28, 2023

The Brønsted acid-controlled switchable synthesis of indoline-fused tetrahydroquinolines and indole-fused benzazepines was developed through hydride transfer-enabled formal [5 + 1] 2] cyclization reactions from indoles N-alkyl o-aminobenzoketones. Indoline, furanone, tetrahydroquinoline hybridized pentacyclic products were unprecedentedly accessed via a cascade condensation/hydride transfer/dearomatization-cyclization/deethylation/nucleophilic addition process. In addition, the undeveloped transfer-involved cyclizations also realized for direct construction benzazepines.

Language: Английский

Citations

21
Eco-Friendly and Efficient Synthesis of 2-Hydroxy-3-Hydrazono-Chromones Through α,β-C(sp2)–H Bond Difunctionalization/Chromone Annulation Reaction of o-Hydroxyaryl Enaminones, Water, and Aryldiazonium Salts DOI Creative Commons
Xiaohong Wang,

Menglin Peng,

Yijin Wang

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(6), P. 1194 - 1194

Published: March 7, 2025

A novel, eco-friendly, and efficient method for constructing 2,3-disubstituted chromone skeletons from readily available water, o-hydroxyaryl enaminones (o-HPEs), aryldiazonium salts has been developed under mild reaction conditions. This α,β-C(sp2)–H bond difunctionalization/chromone annulation strategy is achieved by building two C(sp3)–O bonds a C(sp2)-N bond, which provides practical pathway the preparation of 2-hydroxy-3-hydrazono-chromones in moderate to excellent yields, enabling broad substrate scope good functional group tolerance, as well gram-scale synthesis. protocol offers valuable tool synthesizing diverse functionalized chromones with potential applications drug discovery industrial

Language: Английский

Citations

0
Pd-Catalyzed Coupling of Aryl Chloride, Isocyanides, and Thiocarboxylate To Synthesize Thioamides DOI

Zeyuan Fu,

Ben‐Guang Rong, Liangbin Huang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Although aryl chlorides are among the most abundant and stable aromatic electrophiles, coupling of with isocyanides has remained an unsolved challenge. Herein, we report a general transformation chlorides, isocyanides, thiocarboxylates to synthesize thioamides. The sterically hindered electron-rich Josiphos ligand significantly facilitates rate-determining oxidative addition step reduces toxicity toward metal center. combination thiocarboxylate as nucleophile ligands enabled coupling-tolerated various 1°, 2°, 3° which provides rapid, efficient, versatile method for synthesis large quantities thioamides, including those pharmaceutical relevance.

Language: Английский

Citations

0
Pd-Catalyzed Three-Component Coupling of Cyclopropenones via Sequential C–C Bond Activation and Allylation DOI
Zhou Zhang,

Feifei Liang,

Shulin Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4262 - 4267

Published: May 9, 2024

A novel Pd-catalyzed three-component domino reaction for the stereoselective synthesis of highly functionalized allyl cinnamates has been developed. In this protocol, a sequential process C–C bond activation and intermolecular allylic substitution was well-organized. The key transformation is in situ generated hydrolysis product cyclopropenone, which triggered new with vinylethylene carbonates. mechanism investigated, demonstrating high stereoselectivity excellent atomic economy process.

Language: Английский

Citations

3
Ag-Catalyzed Selective C–C Bond Activation of Cyclopropenones to Access α-Alkylidene Lactones DOI
Shulin Zhang,

Zhao-Bing Wu,

Chunxin Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6120 - 6124

Published: July 11, 2024

A novel Ag-catalyzed ring opening of unsymmetric cyclopropenones for the stereoselective synthesis a diverse range α-alkylidene lactones has been developed. In this protocol, two different C-C(O) bonds were distinguished, demonstrating selective C-C bond activation. This reaction features wide substrate scope, good functional group compatibility, and high atom economy, providing versatile general approach to construction lactones.

Language: Английский

Citations

3
An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones DOI
Liu‐Liang Mao, Yunyun Liu, Jie‐Ping Wan

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110784 - 110784

Published: Dec. 1, 2024

Language: Английский

Citations

3
Access to Chromenopyrrole via Tandem [3 + 2] Cycloaddition and Intramolecular C–O Coupling DOI
Bubul Das, Nikita Chakraborty, Hirendra Nath Dhara

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 1331 - 1335

Published: Jan. 3, 2024

A mild and concise method for the synthesis of chromenopyrrole from 2′-hydroxychalcone is devised. The reaction proceeds via an initial [3 + 2] cycloaddition on C═C bond 1,3-dipolarophile, generated in situ by ethyl isocyanoacetate AgOAc. This then followed intramolecular C–O formation with −OH group C5–H pyrrole, leading to chromenopyrroles.

Language: Английский

Citations

2
Dearomative spiroannulation of indoles enabled by the diaza-[1,2]-Wittig rearrangement DOI

Can Luo,

Chun-Yan Guan,

Zhenyu Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1685 - 1691

Published: Jan. 1, 2024

Reported herein is the first diaza-[1,2]-Wittig rearrangement-enabled dearomative spiroannulation reaction of indoles. This protocol features metal-free conditions, a redox-neutral process, broad substrate scope, and good yield.

Language: Английский

Citations

1
De Novo Synthesis of α‐Ketoamides via Pd/TBD Synergistic Catalysis DOI Creative Commons
Jiahe Chen,

Li‐Ren Zhang,

Zhang‐Yang Wang

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: unknown

Published: July 10, 2024

Precisely controlling the product selectivity of a reaction is an important objective in organic synthesis. α-Ketoamides are vital intermediates chemical transformations and privileged motifs numerous drugs, natural products, biologically active molecules. The selective synthesis α-ketoamides from feedstock chemicals safe operationally simple manner under mild conditions long-standing catalysis challenge. Herein, unprecedented TBD-switched Pd-catalyzed double isocyanide insertion for assembling ketoamides aqueous DMSO (hetero)aryl halides pseudohalides reported. effectiveness utility this protocol demonstrated by its diverse substrate scope (93 examples), ability to late-stage modify pharmaceuticals, scalability large-scale synthesis, pharmaceutically Mechanistic studies indicate that TBD key ligand modulates process, thereby selectively providing desired unique manner. In addition, imidoylpalladium(II) complex α-ketoimine amide successfully isolated determined X-ray analysis, confirming they probable catalytic pathway.

Language: Английский

Citations

1