Synthesis of Isoxazoline Derivatives Based on Nitrile Oxide Cycloaddition of Nitroso‐Nitro‐Enamine

Kondacs, Laszlo Andras; Pilipecz, Mihály V.; Mucsi, Zoltán; Balázs, Barbara; Gáti, Tamás; Nyerges, Miklós; Dancsó, András; Nemes, Péter

doi:10.1002/ejoc.201500905

Cited by 15 publications

(3 citation statements)

References 23 publications

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“…The conversion of 3-phospholene oxides 1 to the corresponding 2-phospholene derivatives 4 was first interpreted by means of thermodynamic data, and the olefinicity concept [69][70][71][72]. The calculations were performed at a high MP2/6-311G++(2d,2p) level of theory ( Table 5).…”

Section: Thermodynamic Descriptionmentioning

confidence: 99%

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

Bagi¹,

Herbay²,

Péczka³

et al. 2020

Beilstein J. Org. Chem.

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A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3-phospholene oxides in methanesulfonic acid, or via the formation of cyclic chlorophosphonium salts. Whereas mixtures of the 2- and 3-phospholene oxides formed, when the isomerization of 3-phospholene oxides was attempted under thermal conditions, or in the presence of a base. The mechanisms of the various double bond migration pathways were elucidated by quantum chemical calculations.

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Section: Thermodynamic Descriptionmentioning

confidence: 99%

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

Bagi¹,

Herbay²,

Péczka³

et al. 2020

Beilstein J. Org. Chem.

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“…We investigated the synthetic usefulness of the tetrahydroquinoline core structure (Scheme ). Treatment with NaOH afforded the hydrolyzed product 4 , and stereoselective aminolysis was performed to afford diamide 5 via the ring-opened ketene intermediate . Furthermore, higher reaction temperatures promoted the recyclization to the N -phenethylmaleimide, which is expected to be a useful late stage strategy to convert the aryl amide to an alkyl amide.…”

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confidence: 99%

Redox-Selective Iron Catalysis for α-Amino C–H Bond Functionalization via Aerobic Oxidation

Hwang

Lee

et al. 2019

Org. Lett.

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Single-electron oxidation and α-deprotonation of tertiary anilines using Fe(phen)3(PF6)3 afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford various tetrahydroquinolines. Mechanistically, the Fe(phen) n 2+/3+ catalytic cycle is maintained by O2 or a TBHP oxidant, and the presence of the oxygen bound iron complex, Fe(III)–OO(H), was elucidated by electron paramagnetic resonance and electrospray ionization mass spectrometry. This redox-selective nonheme iron catalyst behaves similarly to bioinspired heme iron catalysts.

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“…Benefiting from the generality of the electrochemical dehydrogenative [4 + 2] cycloaddition reaction over CCHH‐A/CC anode, we investigated the synthetic usefulness by conducting gram‐scale reaction using this electrochemical protocol (Supporting Information, Scheme S1). [ 26‐27 ] As shown in Scheme S1, 2.449 g of product 3a was obtained with 80% yield (Figure S9), demonstrating the gram‐scale reaction ability for the electrochemical method.…”

Section: Resultsmentioning

confidence: 85%

An Electrocatalytic Strategy for Dehydrogenative [4 + 2] Cycloaddition over a Cobalt‐Based Catalyst

Xue

Wang

et al. 2022

Chin. J. Chem.

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Exploring the anodic reaction to substitute conventional oxygen evolution reaction (OER) for the synthesis of complex pharmaceutical molecules is highly attractive. Here, we report an electrocatalytic strategy for dehydrogenative [4+2] cycloaddition of N,N-dialkylanilines with maleimides via dual functionalization of both C(sp 3 )-H and C(sp 2 )-H bonds, by using an electrochemically activated cobalt carbonate hydroxide hydrate supported on carbon cloth (CCHH-A/CC), affording various tetrahydroquinolines with high yields. This electrochemical transformation proceeds with high activity and stability, as well as good substrate compatibility. Mechanism study shows that α-aminoalkyl radical exists in the electrooxidation reaction. This strategy shows significant potential for the synthesis of valuable chemicals by using an electrocatalytic strategy.

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Synthesis of Isoxazoline Derivatives Based on Nitrile Oxide Cycloaddition of Nitroso‐Nitro‐Enamine

Cited by 15 publications

References 23 publications

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

Redox-Selective Iron Catalysis for α-Amino C–H Bond Functionalization via Aerobic Oxidation

An Electrocatalytic Strategy for Dehydrogenative [4 + 2] Cycloaddition over a Cobalt‐Based Catalyst

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