Preparation of GO/Cys-Cu(II) as a novel, effective and recoverable catalyst for the multi component synthesis of spirooxindoles under mild conditions

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1294, P. 136335 - 136335

Published: Aug. 1, 2023

Language: Английский

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Morphological Profiling Identifies the Motor Protein Eg5 as Cellular Target of Spirooxindoles

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(21)

Published: March 16, 2023

Oxindoles and iso-oxindoles are natural product-derived scaffolds that provide inspiration for the design synthesis of novel biologically relevant compound classes. Notably, spirocyclic connection oxindoles with has not been explored by nature but promises to structurally related compounds endowed bioactivity. Therefore, methods their efficient conclusive discovery cellular targets highly desirable. We describe a selective RhIII -catalyzed scaffold-divergent spirooxindole-isooxindoles spirooxindole-oxindoles from differently protected diazooxindoles N-pivaloyloxy aryl amides which includes functional group-controlled Lossen rearrangement as key step. Unbiased morphological profiling corresponding collection in Cell Painting assay efficiently identified mitotic kinesin Eg5 target spirooxindoles, defining unique inhibitor chemotype.

Language: Английский

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Diastereoselective Synthesis of Dihydrobenzofuran Spirooxindoles and Their Transformation into Benzofuroquinolinones by Ring Expansion of Oxindole Core

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5142 - 5147

Published: March 28, 2024

A mild and efficient approach for the diastereoselective synthesis of dihydrobenzofuran spirooxindoles using 3-chlorooxindoles imines is presented. This process involves a formal [4 + 1] annulation, yielding product with excellent diastereoselectivity. Furthermore, novel method constructing benzofuroquinolinone scaffolds through ring expansion oxindoles has been established. lactam to quinolinone skeleton. Besides, one-pot procedure creating from also provided.

Language: Английский

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A sequential multicomponent reaction toward the construction of a novel contiguous imino-thiazolidinone grafted dispiroheterocyclic scaffolds

Synthetic Communications, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 12

Published: Jan. 29, 2025

Synthesis of structurally intriguing iminothiazolidinone tethered dispiropyrrolizidine/pyrrolothiazole hybrids have been achieved with complete regio- and diastereoselectivity in excellent yields via a one-pot three component 1,3-dipolar cycloaddition strategy employing alkyl-2-[(Z)-4-oxo-3-aryl/alkyl-2-(arylimino)thiazolidin-5-ylidene] acetates as dipolarophiles azomethine ylide derived from two cyclic ketones (isatin acenaphthaquinone) amino acids (l-proline l-thiaproline) using biodegradable deep eutectic solvent. During the entire transformation, additional bonds are formed generation four stereogenic carbons target molecule single step reaction. The synthesized compounds were elucidated NMR spectroscopic studies, regio-and stereoselectivity was determined through crystal X-ray diffraction study.

Language: Английский

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Mechanistic Study on the Asymmetric Cascade Michael Addition of Alkynone and Oxindole Catalyzed by Chiral Guanidine

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

Density functional theory (DFT) calculations with the M06-2X-D3 were used to get mechanistic investigation and stereoselectivity of cascade Michael addition alkynone oxindole, catalyzed by a chiral guanidine-amide compound. The reaction proceeded through two-step synergistic process involving sequential C–C C–O bond formation, together an H-shift. Because high energy barriers 33.5 kcal mol−1 (for construction) 41.3 mol–1 construction), was difficult proceed without catalyst. guanidine catalyst facilitated generation enolized oxindole species nucleophilicity, activating both enolate via ion-pairing multiple hydrogen bonding, significantly lowering activation barriers. combination unit sulfonamide backbone created excellent semiclosed environment, promoting asymmetric induction. Due steric effects from ortho- para-substituted iPr groups in SO2Ar, bulky Cy group, backbone, SS-configuration spirocyclization product enantio- diastereoselectivity formed predominantly. E/Z selectivity formation key α,β-unsaturated ketone intermediate influenced catalyst-substrate interactions. Extension alkyl chain at 3-position substrate led more difficult, hindering construction spirooxindoles.

Language: Английский

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Dipolarophile-Controlled Regioselective 1,3-Dipolar Cycloaddition: A Switchable Divergent Access to Functionalized N-Fused Pyrrolidinyl Spirooxindoles

International Journal of Molecular Sciences, Journal Year: 2023, Volume and Issue: 24(4), P. 3771 - 3771

Published: Feb. 13, 2023

N-fused pyrrolidinyl spirooxindole belongs to a class of privileged heterocyclic scaffolds and is prevalent in natural alkaloids synthetic pharmaceutical molecules. To realize the switchable synthesis divergent spirooxindoles for further biological activity evaluation via substrate-controlled strategy, chemically sustainable, catalysis-free, dipolarophile-controlled three-component 1,3-dipolar cycloaddition isatin-derived azomethine ylides with diverse dipolarophiles described this work. A total 40 functionalized were synthesized 76–95% yields excellent diastereoselectivities (up >99:1 dr). The these products can be well-controlled by employing different 1,4-enedione derivatives as EtOH at room temperature. This study provides an efficient strategy afford spectrum natural-like potentially bioactive spirooxindoles.

Language: Английский

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A Sulfonic Acid Polyvinyl Pyridinium Ionic Liquid Catalyzes the Multi-Component Synthesis of Spiro-indoline-3,5′-pyrano[2,3-d]-pyrimidines and -Pyrazines

Molecules, Journal Year: 2023, Volume and Issue: 28(9), P. 3663 - 3663

Published: April 23, 2023

A sulfonated poly-4-vinyl pyridinium (PVPy-IL-B-SO3H) containing an acidic pyridinium/HSO3- ionic liquid moiety was prepared and used as a catalyst for the three-component reaction of malononitrile with 1-alkylindoline-2,3-diones 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione or methyl 5-hydroxy-1H-pyrazole-3-carboxylate, leading to 6'-amino-5'-cyano-2-oxo-2'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-3'-carboxylates -3,4'-pyrano[2,3-d]pyrimidine]-6'-carbonitrile derivatives under ultrasonic irradiation conditions. The solid allows easy separation, is cheap, produces high yields mild conditions, does not require column chromatography product isolation purification.

Language: Английский

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Tandem Michael–anti-Michael Addition-Mediated Orthogonal Strapping of Diynones: Regioselective Spirocyclopentannulation of Oxindoles and Pyrazolones and DFT Validation

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 87(1), P. 884 - 891

Published: Dec. 23, 2021

An efficient protocol involving the transformation of sequentially generated recursive anions from heterocyclic precursors to orthogonally strap diynones through one pot transition-metal-free spirocyclopentannulation has been devised, employing oxindoles and pyrazolones as prototypical platforms. Insights into these regioselective tandem Michael–anti-Michael processes have gleaned DFT calculations.

Language: Английский

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Substrate-Controlled Regioselectivity Switchable [3 + 2] Annulations To Access Spirooxindole Skeletons

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(12), P. 8158 - 8169

Published: June 8, 2022

The additive-free [3 + 2] annulation from isatins, amino acids with 2-styrylbenzoxazoles, was described, providing a series of functional and structurally complex 3,3'-pyrrolidinyl-spirooxindole derivatives containing four contiguous two quaternary stereogenic centers in high yields (up to 95%) excellent diastereoselectivities >25:1 dr). Interestingly, the reaction exhibits switchable regioselectivity depending on substrate acids. With proline or thioproline as substrate, afforded α-regioselective spirooxindole skeletons. In contrast, when piperidine acid is provided γ-regioselective

Language: Английский

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Synthesis of spiroindolenine-3,3′-pyrrolo[2,1-b]quinazolinones through gold(i)-catalyzed dearomative cyclization of N-alkynyl quinazolinone-tethered indoles

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(10), P. 2069 - 2074

Published: Jan. 1, 2022

An efficient gold( i )-catalyzed dearomative cyclization of N -alkynyl quinazolinone-tethered C2-substituted indoles to prepare various spiroindolenine-3,3′-pyrrolo[2,1- b ]quinazolinones in good excellent yields is reported.

Language: Английский

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