Construction of 3,4-Dihydroquinolone Derivatives through Pd-Catalyzed [4+2] Cycloaddition of Vinyl Benzoxazinanones with α-Alkylidene Succinimides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3279 - 3291

Опубликована: Фев. 20, 2024

The construction of 3,4-dihydroquinolone derivatives has attracted a considerable amount attention due to their extensive applications in medicinal chemistry. In this study, we present the Pd-catalyzed [4+2] cycloaddition vinyl benzoxazinanones with α-alkylidene succinimides for efficient synthesis 3,4-dihydroquinolones. This approach presents numerous advantages, including ready availability starting materials, mild reaction conditions without use additional bases, and wide range substrates. particular, all desired products can be easily afforded high yields (≤99%) excellent diastereoselectivities (>20:1). practicality reliability strategy were demonstrated by successful scale-up subsequent straightforward synthetic transformations.

Язык: Английский

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Successive Hydrolysis and Transfer Hydrogenation of 2-Chloroquinolines to 3,4-Dihydroquinolones

New Journal of Chemistry, Год журнала: 2024, Номер 48(41), С. 17700 - 17705

Опубликована: Янв. 1, 2024

A practical and efficient platform for the synthesis of 3,4-dihydroquinolones through successive hydrolysis transfer hydrogenation was presented. wide range 2-chloroquinolines were compatible with this catalytic system in excellent yields.

Язык: Английский

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Rh-catalyzed hydrogenation of the carbon–carbon double bond in carbostyril derivatives using [Rh(cod)2]BF4 and Et3SiH under mild conditions

Tetrahedron Letters, Год журнала: 2023, Номер 129, С. 154739 - 154739

Опубликована: Сен. 7, 2023

Язык: Английский

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Synthesis of optical active tetramethyl-1,1′-spirobiindane-based iodoarenes and evaluation of their use as axially chiral organocatalysts

Tetrahedron Letters, Год журнала: 2022, Номер 109, С. 154157 - 154157

Опубликована: Сен. 17, 2022

Язык: Английский

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Synthesis of highly functionalized dihydroquinolinones via a tandem benzylation/intramolecular C–N coupling strategy

Tetrahedron, Год журнала: 2024, Номер 155, С. 133865 - 133865

Опубликована: Фев. 17, 2024

Язык: Английский

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Synthesis of N-Alkyl-3-[2-oxoquinolin-1(2H)-yl]propanoic Acid Derivatives and Related Compounds: Cytotoxicity and EGFR Inhibition of Some Propanamide Derivatives

ACS Omega, Год журнала: 2024, Номер unknown

Опубликована: Июль 16, 2024

A series of 20 new structure-modified quinolin-2-one derivatives were prepared for biological evaluation. This was successfully achieved based on chemoselective reactions heterocyclic amides with acrylic acid derivatives, which gave 3-[2-oxoquinolin-1-(2

Язык: Английский

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Pd‐Catalyzed Cyclization of o‐Iodoanilines with Acrylates or Acrylic Acids: A Convenient One‐Step Route to 2‐Quinolinones

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 23, 2024

Abstract A convenient and general method for the construction of 2‐quinolinones was developed in this paper. The Pd‐catalyzed cyclization reaction various o ‐iodoanilines with acrylates or acrylic acids proceeded smoothly to produce 28–>99 % yields. key achieve is utilize suitable base, such as potassium pivalate acetate. Various synthetically useful functional groups, halogen atoms, methoxycarbonyl, nitro remained intact during reaction. effects catalyst base on kinetic experiments were investigated understand aspect

Язык: Английский

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Acid‐catalyzed recyclization of spiroindolinepyrano[3,2‐b]pyrans to 3,4‐dihydroquinolinone derivatives containing allomaltol fragment

Journal of Heterocyclic Chemistry, Год журнала: 2023, Номер 60(8), С. 1427 - 1436

Опубликована: Июнь 1, 2023

Abstract For the first time, we developed a novel one‐step method for synthesis of substituted 3,4‐dihydroquinolinones with allomaltol moiety. The suggested approach includes acid‐catalyzed recyclization spiroindolinepyrano[3,2‐ b ]pyrans which can be obtained by multicomponent reaction 3‐hydroxy‐4‐pyranones, isatins and malononitrile. described transformation is distinctive feature 3‐hydroxy‐4‐pyranone derivatives not typical other heterocyclic enols. advantages considered are employment easily accessible starting materials simple work‐up procedure avoid chromatographic purification. structure one synthesized products was determined x‐ray diffraction.

Язык: Английский

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One-Pot Synthesis of Highly Functionalized Dihydroquinolinones Via Tandem Benzylation/Intramolecular C-N Coupling Strategy

Опубликована: Янв. 1, 2023

A tandem strategy on sequential base controlled benzylation/Pd-catalyzed secondary amide arylation was developed for one-pot synthesis of highly functionalized hydroquinolin-2-ones. This provided a concise route towards diverse 3-cyano substituted hydroquinolin-2-ones in satisfactory yields, given that three bonds, one ring and quaternary carbon stereocenter pot.

Язык: Английский

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A Method for the Synthesis of 1,2,3,4‐Tetrahydroquinolines through Reduction of Quinolin‐2(1H)‐ones Promoted by SmI₂/H₂O/Et₃N

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(47)

Опубликована: Ноя. 22, 2022

Abstract The reduction of quinolin‐2(1 H )‐ones to 1,2,3,4‐tetrahydroquinolines promoted by SmI 2 / O/ Et 3 N is reported for the first time. This reaction involving amides proceeds through C−O bond cleavage. A new method synthesis in mild conditions developed.

Язык: Английский

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