Photoredox-catalyzed procedure for carbamoyl radical generation: 3,4-dihydroquinolin-2-one and quinolin-2-one synthesis

Petersen, Wade F.; Taylor, Richard J. K.; Donald, James R.

doi:10.1039/c7ob01274h

Cited by 53 publications

(22 citation statements)

References 95 publications

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“…Amide bond (or peptide bond) is the basic structure of protein. Hexa-lactam skeleton widely exists in natural products and small-molecule active compounds, which has an important biological significance as well as research value [38,39]. For example, compound UK224671 containing the skeleton has neurohormone 2 (NK2) receptor antagonism [37], and AM-8553 has a better effect for MDM2-p53 inhibition [38].…”

Section: Analysis Of Compoundsmentioning

confidence: 99%

Identification and Analysis of Secondary Metabolites from CH₃OH/H₂O Extract of Metacordyceps Neogunnii

et al. 2019

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Secondary metabolites are considered to be the major compounds in Cordyceps with anti-tumor, anti-aging and immunity-enhancing effects. The molecular structures of secondary metabolites form the basis for the development and utilization of Cordyceps. Metacordyceps neogunnii is an important Cordyceps resource, but less study has been made on the molecular structure of its secondary metabolites. In this study, gas chromatography-mass spectrometry (GC/MS) and ultra performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF/MS) were used to analyze and identify the secondary metabolites from CH3OH/H2O extract of Metacordyceps neogunnii. The results show that a total of 22 compounds were identified by GC-MS, including 2 n-alkanes, 1 isoparaffin, 1 cycloalkane, 6 olefins and 13 esters. The predominant compounds were (E)-ocimene, (E)-β-ocimene, methyl oleate, dioctyl adipate, methyl palmitate and methyl linoleate, obtained by means of GC/MS. Five distince classes of secondary metabolites were speculated: 3 polypeptides, 2 esters, 1 isoflavone, 1 isoindrone and 3 amides, from which 10 compounds were detected using UPLC-Q-TOF/MS. (R)-N-((1-(((9H-fluorene-9-yl) methoxy) carbonyl) pyrrolidine-2-yl) methyl)-N-(2-(6-benzoylamino-9H-purin-9-yl) acetyl) glycine, benzyl (5-(2-((3-(2, 3-dihydrobenzo[b] [1, 4] dioxin-6-yl)-4-carbonyl-4H-chromene-7-yl) oxo) acetylamino) amyl) carbamate, 5, 5’-((propane-2, 2-diyl (4, 1-phenylene)) bis (oxo)) bis (2-(naphthalene-1-yl) isoindoline-1, 3-dione), 1-dodecylazepine-2-one and other compounds were the first detected in Metacordyceps neogunnii.

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Section: Analysis Of Compoundsmentioning

confidence: 99%

Identification and Analysis of Secondary Metabolites from CH₃OH/H₂O Extract of Metacordyceps Neogunnii

et al. 2019

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“…Following radical generation from a substrate e.g. via the oxidative quenching of an excited-state photoredox catalyst (PC * → PC +1 ), it was anticipated that reagent 1 would intercept open-shell species to initiate a cascade process through radical addition to the olefin,9 affording adduct 2 which would readily expel dinitrogen to produce iminyl radical 3 10. Subsequent fragmentation of iminyl radical 3 through α-C–C bond cleavage and ejection of the stabilised 2-hydroxypropyl radical 4 was envisaged to drive the formation of the nitrile functionality 11.…”

Section: Introductionmentioning

confidence: 99%

Radical cyanomethylation via vinyl azide cascade-fragmentation

Donald

Berrell

2019

Chem. Sci.

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“…Thereafter, Chen and Chiao reported the adition of α‐amino‐alkyl radicals to aroyl‐hydrazones (Scheme 23b) [67b] . More recently, Feng and Donald, independently described cascade cycloadditions between N ‐aryl‐carbamoyl radicals and electron‐poor alkenes (Scheme 23c–d) [67c–e] …”

Section: Recent Developments On the Photocatalytic Synthesis Of Quinolinone Derivativesmentioning

confidence: 99%

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

Correia

Santos

Pissinati

et al. 2021

The Chemical Record

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Over the last decade, visible‐light photocatalysis has proved to be a powerful tool for the construction of N‐heterocyclic frameworks, important constituents of natural products, insecticides, pharmacologically relevant therapeutic agents and catalysts. This account highlights recent developments and established methods towards the photocatalytic cascades for preparation of different classes of N‐heterocycles, giving emphasis on our contribution to the field.

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Photoredox-catalyzed procedure for carbamoyl radical generation: 3,4-dihydroquinolin-2-one and quinolin-2-one synthesis

Abstract: A mild, reductive carbamoyl radical generation under photoredox catalysis gives access to substituted 3,4-dihydroquinolin-2-ones, including spirocyclic systems, and aromatic quinolin-2-ones.

Cited by 53 publications

References 95 publications

Identification and Analysis of Secondary Metabolites from CH₃OH/H₂O Extract of Metacordyceps Neogunnii

Identification and Analysis of Secondary Metabolites from CH₃OH/H₂O Extract of Metacordyceps Neogunnii

Radical cyanomethylation via vinyl azide cascade-fragmentation

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

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Photoredox-catalyzed procedure for carbamoyl radical generation: 3,4-dihydroquinolin-2-one and quinolin-2-one synthesis

Abstract: A mild, reductive carbamoyl radical generation under photoredox catalysis gives access to substituted 3,4-dihydroquinolin-2-ones, including spirocyclic systems, and aromatic quinolin-2-ones.

Cited by 53 publications

References 95 publications

Identification and Analysis of Secondary Metabolites from CH3OH/H2O Extract of Metacordyceps Neogunnii

Identification and Analysis of Secondary Metabolites from CH3OH/H2O Extract of Metacordyceps Neogunnii

Radical cyanomethylation via vinyl azide cascade-fragmentation

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

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Product

Resources

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Identification and Analysis of Secondary Metabolites from CH₃OH/H₂O Extract of Metacordyceps Neogunnii

Identification and Analysis of Secondary Metabolites from CH₃OH/H₂O Extract of Metacordyceps Neogunnii