Synthesis of γ-Pyrones and N-Methyl-4-pyridones via the Au Nanoparticle-Catalyzed Cyclization of Skipped Diynones in the Presence of Water or Aqueous Methylamine

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(13), С. 8525 - 8533

Опубликована: Июнь 9, 2022

Supported Au nanoparticles on TiO2 catalyze the hydration/6-endo cyclization of skipped diynones to γ-pyrones in aqueous dioxane, via triple bond activation. The isomeric 3(2H)-furanones which could be formed through a competing and often prevailing 5-exo pathway using homogeneous ionic Au(I) catalysts were not seen. reaction does proceed initial 1,3-transposition their corresponding conjugated 1,3-diynone isomers. If methylamine is added, N-methyl-4-pyridones are exclusively 69-79% yields an analogous hydroamination/Au-catalyzed 6-endo pathway.

Язык: Английский

---

Aliphatic Alcohol Hydroxyl‐Directed One‐Pot Stepwise Synthesis: A Concise Synthesis of 1H‐pyrrolo[3,4‐b]quinoline‐1,3(2H)‐diones

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(15), С. 2588 - 2593

Опубликована: Июль 12, 2023

Abstract A concise and flexible protocol to assemble structurally diverse 1 H ‐pyrrolo[3,4‐ b ]quinoline‐1,3(2 )‐diones (29 examples, 70–87% yields) has been developed via one‐pot stepwise synthesis. The potentially valuable quinine‐fused heterocycles were synthetized by utilizing aliphatic alcohol hydroxyl as directing group which promoted a sequential transformation form functionalized aminomaleimides, then underwent an I 2 ‐oxidized tandem annulations. This route involved the formation of multiple new chemical bonds (C=N, 2C−N, C−C) in fashion under mild conditions.

Язык: Английский

---

A Novel Ring-Opening/Ring-Closing Cascade Reaction Selectively Induced by Aliphatic Primary Amine Using Phenolic Hydroxyl as a Traceless Directing Group

Synthesis, Год журнала: 2023, Номер 55(09), С. 1441 - 1450

Опубликована: Янв. 12, 2023

Abstract An interesting ring-closing/ring-opening cascade reaction selectively induced by aliphatic primary amine for the synthesis of functionalized aminomaleimides is described. This work features phenolic hydroxyl as a traceless directing group that forms critical six-membered intermediate and then lactone ammonolysis/intramolecular amidation sequence. two-step, one-pot practical protocol has broad substrate scope (39 examples) delivers structurally diverse in good to excellent yields.

Язык: Английский

---

Microwave-assisted DABCO-promoted regioselective [3 + 3] tandem cyclization: synthesis of pyrrolo[3,4-b]pyridine-4-ones from trifluoromethyl-alkynyl esters and α-aminomaleimide

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(29), С. 6039 - 6045

Опубликована: Янв. 1, 2023

A microwave-assisted DABCO-promoted strategy for the regioselective synthesis of pyrrolo[3,4-b]pyridine-4-one derivatives has been developed from [3 + 3] annulation α-aminomaleimide with substituted ethyl 2-butynoate. The characteristic features this methodology include operational simplicity, high regioselectivity, metal-free reaction conditions, and short times. potential utility these methods in biological chemistry medicinal science applications is highlighted.

Язык: Английский

---

Cs2CO3‐Promoted Alkylation of 3‐Cyano‐2(1H)‐pyridones: Anticancer Evaluation and Molecular Docking

ChemPlusChem, Год журнала: 2024, Номер unknown

Опубликована: Июнь 6, 2024

Abstract Herein, a Cs 2 CO 3 ‐promoted N ‐alkylation of 3‐cyano‐2(1 H )‐pyridones containing alkyl groups with diverse halides to synthesize ‐alkyl‐2‐pyridones over O ‐alkylpyridines is reported. The use dihalides resulted in complex mixtures ‐ and ‐alkylated products. primary factor influencing regioselectivity these reactions the electronic effects substituents on 2(1 )‐pyridone ring, as evidenced by preferential formation upon introduction aryl groups. Remarkably, we efficiently employed CuAAC Ti(O i ‐Pr) 4 ‐catalyzed amidation functionalize propargyl ester groups, leading synthesis 1,2,3‐triazoles amides, respectively. Moreover, 10 b d displayed remarkable selectivity toward A‐498 renal cancer cell line growth inhibition percentages (%GI) 54.75 67.64, binding modes compounds PIM‐1 kinase enzyme were determined through molecular docking studies.

Язык: Английский

---

A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(4), С. 1550 - 1550

Опубликована: Янв. 1, 2023

A novel, efficient and practical route to the preparation of (Z)-N-vinyl five-membered cyclic N,O-acetal derivatives utilized by continuous flow technology has been developed.The tandem cyclization reaction uses Schiff base imine as an intermediate, followed addition hydroxyl group alkynyl ester under action alkali, undergoing a unique intramolecular rearrangement synthesize acetal derivatives.The whole cascade process generates new C-O bond C-N bond.In addition, application can accurately control three-component pathway compared with traditional batch reaction, which inhibit generation by-products between two components provide series structurally diverse nitrogen-and oxygen-containing heterocycles in short time high yields (81%～90%).

Язык: Английский

---

Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

ChemistrySelect, Год журнала: 2024, Номер 9(45)

Опубликована: Ноя. 30, 2024

Abstract A concise and practicable route to the synthesis of multisubstituted 2‐pyridones via a four‐component one‐pot stepwise cyclization catalyzed by Cs 2 CO 3 has been developed. During this transformation, two new C‐C bonds C‐N were generated through an intermolecular condensation/aza‐Michael reaction/intermolecular Michael addition/intramolecular sequence. The alternative protocol offers complementary provide series structurally diverse polysubstituted (21 examples) in good excellent yields (52–81%) from easily available raw materials arylamines, dialkyl acetylenedicarboxylate, 1,3‐dicarbonyl compounds, trialkyl orthoformate under mild conditions. It might opportunities for discovery 2‐pyridones‐containing drugs.

Язык: Английский

---

Highly Selective Synthesis of (Z)-N-vinyl Ring N,O-Acetal Derivatives by Multi-component Continuous Flow

Acta Chimica Sinica, Год журнала: 2022, Номер 80(11), С. 1463 - 1463

Опубликована: Янв. 1, 2022

A three-component synthetic method for the efficient preparation of (Z)-N-vinyl ring N,O-acetal derivatives under continuous flow technology was developed.Recently, applied in organic synthesis has attracted significant attention, and become useful alternatives to conventional operations.Furthermore, advances translation from ''batch'' ''flow'' mode have expanded rapidly, offering valuable opportunities a variety research areas.By using cheap readily available chemicals as reaction's starting material, advantages excellent reaction process control, high surface area volume ratio, heat exchange, effective mixing, reduced time, so on.The controllable series cyclization takes place flow, which precisely regulates o-hydroxybenzylamine with aldehydes form Schiff base intermediate.Then intermediate is discharged time undergoes an oxa-Michael addition diethyl acetylenedicarboxylate conditions.It experiences unique intramolecular rearrangement C-O C-N bonds.In synthesis, amines are mixed tube placed B. First, mixture injected into first plastic coil reactor heating bath (HB1), 80 ℃ kept 10 min.The transported next step acetylene dicarboxylate B small T-shaped mixer, second glass column (HB2), retained 40 min.Finally, nitrogen-, oxygen-containing six-membered or seven-membered heterocyclics were synthesized selectivity, two-step only 50 application can avoid problems involving incomplete two-component, more side reactions, provides alternative assembling multicomponent selectivity yield (up 96%), providing reference high-value conversion chemical raw materials.

Язык: Английский

---