Tunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity

Organic Letters, Год журнала: 2023, Номер 25(12), С. 2139 - 2144

Опубликована: Март 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]

Язык: Английский

---

Transition‐Metal‐Free C(sp²)‐H Dithiocarbamation and Chromone Annulation Cascade for 3‐Dithiocarbamyl Chromone Synthesis

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(20), С. 4811 - 4816

Опубликована: Авг. 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

Язык: Английский

---

Copper-Catalyzed Enaminone C(sp²)–N Bond Phosphonation for Stereoselective Synthesis of Alkenylphosphonates

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(14), С. 9861 - 9868

Опубликована: Июнь 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.

Язык: Английский

---

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

Organic Letters, Год журнала: 2021, Номер 23(13), С. 5049 - 5053

Опубликована: Июнь 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).

Язык: Английский

---

Metal-free enaminone C–N bond cyanation for the stereoselective synthesis of (E)- and (Z)-β-cyano enones

Chemical Communications, Год журнала: 2021, Номер 57(72), С. 9112 - 9115

Опубликована: Янв. 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.

Язык: Английский

---

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

ACS Catalysis, Год журнала: 2022, Номер 12(18), С. 11428 - 11435

Опубликована: Сен. 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

Язык: Английский

---

Comprehensive Review of Dihydro‐2H‐pyrrol‐2‐one Derivatives

ChemistrySelect, Год журнала: 2025, Номер 10(1)

Опубликована: Янв. 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.

Язык: Английский

---

Acid-Catalyzed, Metal- and Oxidant-Free C=C Bond Cleavage of Enaminones: One-Pot Synthesis of 3,4-Dihydroquinazolines

Molecules, Год журнала: 2025, Номер 30(2), С. 350 - 350

Опубликована: Янв. 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.

Язык: Английский

---

A New, Convenient Way to Fully Substituted α,β-Unsaturated γ-Hydroxy Butyrolactams

International Journal of Molecular Sciences, Год журнала: 2023, Номер 24(12), С. 10213 - 10213

Опубликована: Июнь 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.

Язык: Английский

---

Selective cleavage and reconstruction of C–N/C–C bonds in saturated cyclic amines: tunable synthesis of lactams and functionalized acyclic amines

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(18), С. 5118 - 5123

Опубликована: Янв. 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.

Язык: Английский

---