Rh‐catalyzed three‐component synthesis of diverse N‐aryl pyrazoles via cascade pyrazole annulation and aryl C‐H addition to alkenes DOI

Xinyuan Wen,

Jie‐Ping Wan, Ming Zhang

et al.

Applied Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 38(9)

Published: July 5, 2024

A novel Rh‐catalyzed three‐component synthesis of N ‐( o ‐alkylaryl) pyrazoles via cascade pyrazole annulation and aryl C‐H conjugate addition to alkenes has been developed with enaminones, hydrazines, functionalized as starting materials. The raw materials used in this reaction are simple, cheap, readily available, the reactions feature excellent step economy by furnishing products formation a ring key activation one‐step operation. Moreover, proceeds smoothly under air atmosphere, making it easy operate.

Language: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

Citations

27

Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones DOI

Mingshuai Zhang,

Meichen Liu,

Yuetong Qiu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2363 - 2369

Published: March 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Language: Английский

Citations

13

Selective synthesis of pyridazin-fused chromones and 3-pyridazinyl chromones through intermolecular chromone annulation of o-hydroxyphenylenaminones with aryldiazonium salts DOI
Siyu Song,

Zhilai Zhang,

Menglin Peng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3906 - 3912

Published: Jan. 1, 2024

A chemodivergent and skeleton-controllable annulation reactions of readily available o -HPEs aryldiazonium salts was described for the synthesis highly functionalized pyridazine-fused chromones with high antiviral activity higher safety.

Language: Английский

Citations

11

I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations DOI
You Zhou, Li‐Sheng Wang,

Shuang‐Gui Lei

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(1), P. 109799 - 109799

Published: March 20, 2024

Language: Английский

Citations

10

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

Accessing 7,8-Dihydroquinoline-2,5-diones via Rh-Catalyzed Olefinic C–H Activation/[4+2] Cyclization DOI
Xueqing Liu,

Sijia Shi,

Wenqian Ding

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5136 - 5140

Published: June 7, 2024

Herein, we report a rhodium-catalyzed C–H activation/[4+2] cyclization reaction between α,β-unsaturated amides and iodonium ylides for the synthesis of novel 7,8-dihydroquinoline-2,5-diones analogues. This protocol provides series pyridones fused with saturated cycles good functional group compatibility, water air tolerance, to excellent yields under mild green conditions. Additionally, scale-up can be smoothly performed as low 0.25 mol % catalyst loading. Recycling experiments different transformation were also carried out demonstrate potential synthetic utility this protocol.

Language: Английский

Citations

8

Annulative Nonaromatic Newman–Kwart-Type Rearrangement for the Synthesis of Sulfur Heteroaryls DOI
Yunyun Liu,

Leiling Deng,

Haijin Guo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 46 - 50

Published: Dec. 27, 2023

By employing enaminones and thiuram disulfides as starting materials, the frontiers of Newman–Kwart rearrangement have been expanded to alkenyl system for first time. In addition, instead leading formation simple carbamothioates, has led unprecedented construction S-heteroaryls. Depending on differences in enaminone structure, efficient synthesis functionalized isothiazoles thiophenes achieved.

Language: Английский

Citations

19

Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions DOI
Xing He,

Kangli Liu,

Shengnan Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7425 - 7430

Published: Aug. 22, 2024

Presented herein is an atom- and step-economical method enabling the precise assembly of a heptacyclic scaffold containing both azocine indoline units through cascade reactions indolin-1-yl(aryl)methanimines with diazo indanediones. The formation products involves C–H bond activation double carbene insertion followed by intramolecular condensation, retro-[2 + 2] cycloaddition, recyclization. This reaction not only provided concise straightforward strategy for synthesis otherwise difficult to obtain compounds from readily available substrates but also disclosed unprecedented mode derivatives compounds. In general, this novel synthetic protocol has advantages, such as easily obtainable substrates, structurally sophisticated products, procedure, good compatibility diverse functional groups, ready scalability. Moreover, thus obtained showed decent antiproliferative activity against three human cancer cell lines.

Language: Английский

Citations

8

Photocatalytic Pyridine Synthesis with Enaminones and TMEDA under Metal-Free Conditions DOI

Junlong Zeng,

Tao Zhou, Jianchao Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 11060 - 11066

Published: July 24, 2024

Reported herein is a new photocatalytic annulation for the synthesis of 2,3,4,6-tetrasubstituted pyridines with enaminones and N,N,N′,N′-tetramethyl ethylenediamine (TMEDA). The reactions take place without requiring transition metal reagent provide products broad scope. methyl in TMEDA acts as carbon source pyridine ring construction, BrCF2CO2Et plays role terminal oxidant free radical quenching.

Language: Английский

Citations

7

Oxidative Free-Radical C(sp2)–H Bond Chlorination of Enaminones with LiCl: Access to Highly Functionalized α-Chlorinated Enaminones DOI

Yunhua Xie,

Zhilai Zhang,

Biao Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8521 - 8530

Published: June 3, 2024

An oxidative free-radical C(sp2)–H bond chlorination strategy of enaminones has been developed by using LiCl as a chlorinating reagent and K2S2O8 an oxidant. This transformation provides new straightforward synthetic methodology to afford highly functionalized α-chlorinated with Z-configuration in good excellent yields.

Language: Английский

Citations

6