Ugi-post functionalization, from a single set of ugi-adducts to two distinct heterocycles by microwave-assisted palladium-catalyzed cyclizations: tuning the reaction pathways by ligand switch
| العنوان: | Ugi-post functionalization, from a single set of ugi-adducts to two distinct heterocycles by microwave-assisted palladium-catalyzed cyclizations: tuning the reaction pathways by ligand switch |
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| المؤلفون: | William Erb, Luc Neuville, Jieping Zhu |
| المساهمون: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| المصدر: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2009, 74 (8), pp.3109-15. ⟨10.1021/jo900210x⟩ |
| سنة النشر: | 2009 |
| مصطلحات موضوعية: | Indoles, Magnetic Resonance Spectroscopy, Intramolecular reaction, MESH: Solvents, Ligands, 01 natural sciences, Medicinal chemistry, Dioxanes, chemistry.chemical_compound, aldehydes and isocyanides followed by palladium-XPhos-catalyzed heterocyclization under microwave irradn.), Heterocyclization (prepn. of benzopiperazinone derivs. via four-component Ugi addn. of iodoarylamines with carboxylic acids, MESH: Structure-Activity Relationship, Amide, benzopiperazinone deriv prepn, iodophenylaminocarboxamide prepn heterocyclization palladium XPhos, oxindole deriv prepn, palladium BINAP heterocyclization iodophenylaminocarboxamide, MESH: Ligands, MESH: Cyclization, Microwaves, BINAP, MESH: Indoles, Molecular Structure, Chemistry, Ugi reaction (four-component, prepn. of benzopiperazinone derivs. via four-component Ugi addn. of iodoarylamines with carboxylic acids, Lactam, MESH: Palladium, Palladium, Reaction mechanism, RACT (Reactant or reagent) (aryl, Stereochemistry, MESH: Molecular Structure, [SDV.BC]Life Sciences [q-bio]/Cellular Biology, MESH: Microwaves, 010402 general chemistry, Catalysis, Microwave (irradn, Structure-Activity Relationship, MESH: Quinoxalines, XPhos, Quinoxalines, RACT (Reactant or reagent) (prepn. of benzopiperazinone derivs. via four-component Ugi addn. of iodoarylamines with carboxylic acids, MESH: Dioxanes, Amines Role: RCT (Reactant), 010405 organic chemistry, Ligand, MESH: Magnetic Resonance Spectroscopy, Organic Chemistry, Aldehydes, Carboxylic acids, Isocyanides Role: RCT (Reactant), MESH: Catalysis, 0104 chemical sciences, Oxindoles, Cyclization, Solvents, Ugi reaction |
| الوصف: | International audience; Linear amides 4, prepared in one step by the Ugi four-component reaction, were converted to 3,4-dihydroquinoxalin-3-ones (5) or to 2-(2-oxoindolin-1-yl)acetamides (6) dependent on the catalytic conditions. While microwave irradiation was found to be determinant on the reaction efficiency, the choice of ligand diverged the reaction pathways. Heating a solution of 4 in dioxane/MeCN (v/v = 85/15) under microwave irradiation conditions in the presence of Pd(dba)(2) (0.05 equiv) and Cs(2)CO(3) (2 equiv), using XPhos as a supporting ligand, afforded the 3,4-dihydroquinoxalin-3-ones (5) via an intramolecular N-arylation of the secondary amide. On the other hand, using BINAP as ligand under otherwise identical conditions, intramolecular alpha-CH arylation of tertiary amide occurred to furnish the oxindoles (6). |
| تدمد: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo900210x⟩ |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::398e47eeb97fc01cce37a0b77d0afb36 https://pubmed.ncbi.nlm.nih.gov/19284772 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi.dedup.....398e47eeb97fc01cce37a0b77d0afb36 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15206904 00223263 |
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| DOI: | 10.1021/jo900210x⟩ |