Regioselectivity Inversion in the Cycloaddition Reaction between Stable Nitrile Oxides and Acylalkyne Derivatives
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- Material Type
- 記事
- Author Heading
- Publication Date
- 2025-11-26
- Publication Date (W3CDTF)
- 2025-11-26
- Periodical title
- Ｃｈｅｍ． Ｐｈａｒｍ． Ｂｕｌｌ．
- No. or year of volume/issue
- 73 11
- Volume
- 73
- Issue
- 11
- Pages
- 1065-1074
- Publication date of volume/issue (W3CDTF)
- 2025-11-26
- ISSN (Periodical Title)
- 00092363
- Publication (Periodical Title)
- The Pharmaceutical Society of Japan
- Text Language Code
- en
- Subject Heading
- Target Audience
- 一般
- Standard No. (Other)
- PMID : 41297939
- DOI
- 10.1248/cpb.c25-00471
- Related Material (URI)
- References
- First Total Syntheses of Tetracenomycins C and XNitrile Oxides. VIII. Cyanogen N-Oxide<sup>1</sup>Synthesis of Pyrazoles via Electrophilic CyclizationCycloaddition of nitrile oxides to cyclic and acyclic α,β-unsaturated amides. Frontier orbital interactions and an unexpected steric drift determine regiochemistryChemical space as a source for new drugsTotal Synthesis and Structure Assignment of the Anthrone C‐Glycoside CassialoinAsymmetric Inverse‐Electron‐Demand 1,3‐Dipolar Cycloaddition of C,N‐Cyclic Azomethine Imines: An Umpolung StrategyLigand-Based Design of Allosteric Retinoic Acid Receptor-Related Orphan Receptor γt (RORγt) Inverse AgonistsAn Isoxazole Strategy for Molybdenum-Mediated Synthesis of 5-Mono- and 4,5-Disubstituted 1<i>H</i>-Pyrrole-2,3-dionesNotes- Action of Hydroxylamine, Hydrazine Hydrate, and Phenylhydrazine on 2-Acetoaceto-1-naphtholEfficient and convenient method for the synthesis of isoxazoles in ionic liquidVinylogous hydrazone strategy for the organocatalytic alkylation of heteroaromatic derivativesDansylated Nitrile <i>N</i>‐Oxide as the Fluorescent Dye Clickable to Unsaturated Bonds without CatalystHydrazone Activation in the Aminocatalytic Cascade Reaction for the Synthesis of TetrahydroindolizinesTotal Synthesis of the Antibiotic BE‐43472BInverse-electron-demand Diels–Alder reactions of α,β-unsaturated hydrazones with 3-methoxycarbonyl α-pyronesInverse-Electron-Demand oxa-Diels–Alder Reactions of α-Keto-β,γ-unsaturated Esters and α,β-Unsaturated HydrazonesTotal Synthesis and Absolute Stereochemistry of Seragakinone ABehaviour of nitrile oxides towards nucleophiles. Part III. Dimerisation of aromatic nitrile oxides catalysed by trimethylamineThe recent progress of isoxazole in medicinal chemistryDecomposition of Alkynyl Hydrazones: Synthesis of Allenoates, Dihaloallenoates, and Angularly Fused Tricyclic AzepinesA Study of the Direction of Enolization of Mesitoyl-m-nitrobenzoylmethaneAsymmetric [4+2]‐Cycloaddition of Anthracene Derivatives <i>via</i> Hydrazone ActivationPolyester-Containing α-Cyclodextrin-Based Polyrotaxane: Synthesis by Living Ring-Opening Polymerization, Polypseudorotaxanation, and End Capping Using Nitrile <i>N</i>-OxideUtilization of electron-donating α,β-unsaturated oximes: regioselective inverse 1,3-dipolar cycloaddition of nitronesCycloadditions of Nitrile Oxides to α,β-Unsaturated Aldehydes. Frontier Orbital Interactions and Secondary Orbital Interactions at Work in Determining RegiochemistryNitrile oxides. IX. Basic substituted stable nitrile oxidesAn Efficient New Route for the Synthesis of Some 3‐Hterocyclylquinolinones <i>via</i> Novel 3‐(1,2‐Dihydro‐4‐hydroxy‐1‐methyl‐2‐oxoquinolin‐3‐yl)‐3‐oxopropanal and Their Antioxidant ScreeningSynthesis of 3,5-Disubstituted Isoxazoles and Isoxazolines in Deep Eutectic SolventsPalladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile OxidesStep-by-Step Multifunctionalization of Isoxazoles Based On SEAr Reactions and C–H Direct ArylationsSynthesis of Pyrazoles Utilizing the Ambiphilic Reactivity of HydrazonesMetal-free DBU promoted regioselective synthesis of isoxazoles and isoxazolinesClean and Efficient Synthesis of Isoxazole Derivatives in Aqueous MediaStudies of nitrile oxide cycloadditions, and the phenolic oxidative coupling of vanillin aldoxime by Geobacillus sp. DDS012 from Italian rye grass silageIsoxazolesα-Keto hydrazones in asymmetric aminocatalysis: reactivity through β-amino aza-dienamine intermediatesEfficient Access to Isoxazoles from AlkenesMacromolecular Surface Design: Photopatterning of Functional Stable Nitrile OxidesGold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted CyclobutanesOne-Pot Copper(I)-Catalyzed Synthesis of 3,5-Disubstituted IsoxazolesTarget-Oriented and Diversity-Oriented Organic Synthesis in Drug DiscoveryA Planning Strategy for Diversity‐Oriented SynthesisHydrazones as Singular Reagents in Asymmetric OrganocatalysisAdvances in nitrile oxides chemistryApproach to Tetrodotoxin via the Oxidative Amidation of a PhenolRecent Developments in the Synthesis and Reactivity of Isoxazoles: Metal Catalysis and BeyondA Facile One-Pot Synthesis of 3,5-Disubstituted Isoxazole Derivatives Using Hydroxy (Tosyloxy) Iodobenzene<i>N</i>,<i>N</i>-Dialkylhydrazones in Organic Synthesis. From Simple <i>N</i>,<i>N</i>-Dimethylhydrazones to Supported Chiral AuxiliariesNitrile OxidesBoronic Acid Catalysis for Mild and Selective [3+2] Dipolar Cycloadditions to Unsaturated Carboxylic AcidsFluorescent Probes from Stable Aromatic Nitrile OxidesIsoxazoline derivatives. Part VI. Regioselectivity in the 1,3-dipolar cycloaddition of nitrile oxides to αβ-unsaturated ketonesEfficient and Regioselective One-Pot Synthesis of 3-Substituted and 3,5-Disubstituted IsoxazolesNitrile Oxides. V. Stable Aromatic Nitrile Oxides<sup>1,2</sup>Reversal of Regioselectivity and Enhancement of Rates of Nitrile Oxide Cycloadditions through Transient Attachment of Dipolarophiles to Cyclodextrins1,4‐Diazabicyclo[2.2.2]octane (DABCO) as an Efficient Reagent for the Synthesis of Isoxazole Derivatives from Primary Nitro Compounds and Dipolarophiles: The Role of the BaseThe synthetic and therapeutic expedition of isoxazole and its analogsNitrile OxidesAldehyde <i>N</i>,<i>N</i>‐Dialkylhydrazones as Neutral Acyl Anion Equivalents: Umpolung of the Imine Reactivity1,3‐Dipolar Cycloadditions. Past and FutureC−C Bond-Forming Click Synthesis of Rotaxanes Exploiting Nitrile <i>N</i>-OxideStable Aromatic Nitrile OxidesSynthesis and Antifungal Activities of Furoxan Derivatives Designed as Novel Fungicide.BCSJ Award Article : Pleospdione, A Tricyclic Natural Product with Dense Oxygenation at the A-Ring : Total Synthesis and Incongruity of the Originally Assigned Structure and its C3-Epimer
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- 国立情報学研究所 : CiNii Research
- Original Data Provider (Database)
- Japan Link CenterCrossrefPubMed
- Summary, etc.
- <p>1,3-Dipolar cycloaddition reaction of stable nitrile oxides with <i>α</i>,<i>β</i>-alkynyl hydrazones affords 5-iminoisoxazoles, whereas the reaction of nitrile oxides with <i>α</i>,<i>β</i>-alkynyl carbonyl compounds gives 4-acylisoxazoles. The regioselectivity of the cycloaddition reaction is reversed due to the electron-donating character of the hydrazone group. The 5-iminoisoxazoles are readily converted to the corresponding 4-acylisoxazoles by dehydrazonation.</p>
- DOI
- 10.1248/cpb.c25-00471
- Access Restrictions
- インターネット公開
- Data Provider (Database)
- 科学技術振興機構 : J-STAGE