Base‐Catalyzed [4+2] Annulation of Ynones and Acetates for the Synthesis of 2‐Pyrones DOI
Ting Chen,

Mao-Chun Ye,

Ting Huang

et al.

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

Published: Oct. 30, 2024

Abstract An efficient, practical, and scalable Cs 2 CO 3 ‐catalyzed [4+2] annulation reaction between ynones acetates is presented, wherein serve as the four‐atom partners. This methodology facilitates synthesis of substituted 2‐pyrones with yields ranging from good to excellent. The ready availability starting materials, coupled simplicity protocol, renders this approach highly amenable preparation a diverse range 2‐pyrones. Furthermore, feasibility on gram scale its application in potent selective cyclooxygenase‐2 inhibitor underscore practical significance utility method.

Language: Английский

Tunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity DOI
Wenli Song, Yunyun Liu, Nan Yan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(12), P. 2139 - 2144

Published: March 22, 2023

The three-component reactions of enaminones, α-diazo esters/ketones, and t-butyl nitrite (TBN) for the switchable synthesis isomeric isoxazoles have been realized. catalysis with Cu(II) salt provides 3,4-disubsituted via [3 + 2] cycloaddition. On other hand, Ag(I) identical substrates leads to reversed C3 C4 substitution based on a key [2 1]

Language: Английский

Citations

41
Transition‐Metal‐Free C(sp2)‐H Dithiocarbamation and Chromone Annulation Cascade for 3‐Dithiocarbamyl Chromone Synthesis DOI
Tao Zhang, Weijun Yao, Jie‐Ping Wan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(20), P. 4811 - 4816

Published: Aug. 26, 2021

Abstract The transition‐metal‐free synthesis of 3‐dithiocarbamyl chromones by reacting o ‐hydroxyphenylenaminones with thiurams in the presence KIO 3 and TEMPO is reported. In addition, synthesized herein have been successfully utilized as starting materials pyrimidines 3‐(benzylthio)chromones via featured chromone ring opening C−S bond cleavage, respectively. magnified image

Language: Английский

Citations

46
Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines DOI Creative Commons
Ting Chen, Ting Huang,

Mao-Chun Ye

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(2), P. 350 - 350

Published: Jan. 16, 2025

In this study, we present the HOAc-catalyzed selective cleavage of C=C double bond enaminones, enabling formation a new C–N and C=N for one-pot synthesis 2-substituted 3,4-dihydroquinazolines directly from ynones 2-(aminomethyl)anilines. This method operates in ethanol under transition-metal-free oxidant-free conditions, offering sustainable efficient approach with broad functional group tolerance.

Language: Английский

Citations

1
Copper-Catalyzed Enaminone C(sp2)–N Bond Phosphonation for Stereoselective Synthesis of Alkenylphosphonates DOI
Ting Liu, Wei Li,

Baoli Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(14), P. 9861 - 9868

Published: June 30, 2021

A direct enaminone C–N bond coupling functionalization that generates a new C–P using dialkyl phosphonate for the efficient and stereoselective synthesis of (E)-alkenylphosphonates is reported. The reactions toward target products proceed well with broad scope, disclosing valuable synthetic application enaminones by interesting C(sp2)–N elaboration.

Language: Английский

Citations

33
Tunable Trifunctionalization of Tertiary Enaminones for the Regioselective and Metal-Free Synthesis of Discrete and Proximal Phosphoryl Nitriles DOI

Zhongrong Xu,

Leiqing Fu,

Xia Fang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(13), P. 5049 - 5053

Published: June 17, 2021

This paper reports an unprecedented trifunctionalization of tertiary enaminones for the synthesis phosphoryl nitriles by reactions with diarylphosphine oxides and trimethylsilyl cyanide (TMSCN) without use any metal reagent. Employing tetrabutyl ammonium hydroxide (TBAH) as catalyst (0.2 equiv) enables discrete cyanophosphonation. On other hand, selective proximal cyanophosphonation has been realized in presence acetic acid only (AcOH).

Language: Английский

Citations

31
Metal-free enaminone C–N bond cyanation for the stereoselective synthesis of (E)- and (Z)-β-cyano enones DOI
Ting Liu, Jie‐Ping Wan, Yunyun Liu

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(72), P. 9112 - 9115

Published: Jan. 1, 2021

The C–N bond cyanation of tertiary enaminones has been realized for the stereoselective synthesis both ( E )- and Z )-β-cyano enones under mild metal-free conditions, providing highly practical approaches β-cyano enones.

Language: Английский

Citations

31
Molybdenum-Catalyzed Intermolecular Deoxygenative Cross-Coupling Reactions of 1,2-Diketones with α-Ketoamides DOI

Yuanqing Dong,

Kai Wang, Chun‐Xiang Zhuo

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(18), P. 11428 - 11435

Published: Sept. 6, 2022

Here we describe the Mo-catalyzed intermolecular deoxygenative cross coupling of bench stable and readily accessible1,2-diketones with α-ketoamides, in which three four carbonyl oxygen atoms were eliminated along formations a carbon–nitrogen bond carbon–carbon double one step under Mo-catalysis. Various pyrrol-2-ones secured up to 96% yield by utilizing commercial Mo-catalyst. The synthetic potential current methodology is additionally demonstrated transformations, gram-scale synthesis, derivatization several natural products drug molecules. preliminary mechanistic investigation suggest this cascade process might be initiated via formal N–H insertion followed intramolecular carbonyl–carbonyl olefination reaction, both steps catalyzed single

Language: Английский

Citations

20
Comprehensive Review of Dihydro‐2H‐pyrrol‐2‐one Derivatives DOI Open Access

Benjamin Siddiqui,

Chandra Shekhar Yadav,

Mohd Faiyyaz

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(1)

Published: Jan. 1, 2025

Abstract Heterocyclic chemistry has emerged as a significant field with diverse applications in recent scenarios. Nitrogen‐containing heterocyclic compounds have garnered attention due to their unique physiological characteristics and extensive medicinal utility. Therefore, the dihydro‐2 H ‐pyrrol‐2‐one scaffold is key skeleton for pharmaceutical research its high bioavailability wider synthetic applications. This study found that 1,5‐dihydro‐2 scaffolds can be used many ways. Thus, these been subject of lot years, but preparation main core harder because structure. covers methods over past 15 years synthesize substituted derivatives through variety reaction approaches by utilizing hybrid catalyzing systems, including photocatalysis, electrocatalysis, alkaline catalysts, acid organocatalysts, ionic liquid nanocatalysts, heterogeneous or homogeneous transitional‐metal catalysis (including Cu, Pd, Ni, Ru, Co, Fe, Si, Pt, Zn, etc.), well mechanism. review will encourage researchers exploit catalytic synthesis target compounds.

Language: Английский

Citations

0
A New, Convenient Way to Fully Substituted α,β-Unsaturated γ-Hydroxy Butyrolactams DOI Open Access
А. В. Аксенов, Дмитрий А. Аксенов, Igor A. Kurenkov

et al.

International Journal of Molecular Sciences, Journal Year: 2023, Volume and Issue: 24(12), P. 10213 - 10213

Published: June 16, 2023

The synthesis of novel, highly functionalized 5-hydroxy 3-pyrrolin-2-ones via a two-step procedure involving an addition reaction between KCN and corresponding chalcones, followed by ring condensation the obtained β-cyano ketones with het(aryl)aldehydes under basic conditions is described. This protocol enables preparation various 3,5-di-aryl/heteroaryl-4-benzyl substituted α,β-unsaturated γ-hydroxy butyrolactams, which are subjects significant interest to synthetic organic medicinal chemistry.

Language: Английский

Citations

7
Selective cleavage and reconstruction of C–N/C–C bonds in saturated cyclic amines: tunable synthesis of lactams and functionalized acyclic amines DOI
Yan He, Jintao Yang, Xinying Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(18), P. 5118 - 5123

Published: Jan. 1, 2021

Selective cleavage of C–N/C–C bonds in saturated cyclic amines for the tunable synthesis lactams and functionalized acyclic under promotion oxoammonium salt TBHP presence different additives have been developed.

Language: Английский

Citations

13