SO2ClF‐Promoted Chlorooxidation of Tryptamine Derivatives: Synthesis of 3,3‐Disubstituted Oxindoles DOI
Yu Zheng, Wenguang Lu,

Tianting Ma

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 13(1)

Опубликована: Дек. 7, 2023

Abstract A series of tryptamine derivatives were transformed into their corresponding 3‐chloro‐2‐oxidation products under simple and mild conditions. This protocol is an operationally system that utilizes a single reagent SO 2 ClF plays dual role as both oxidant chloride source enables the construction various 3,3‐disubstituted oxindoles with good functional group tolerance. The transformations product highlight its potential synthetic applications.

Язык: Английский

Unveiling the beauty of cyclopropane formation: a comprehensive survey of enantioselective Michael initiated ring closure (MIRC) reactions DOI Creative Commons

Ramkumar Moorthy,

Waidath Bio-Sawe,

Sagar S. Thorat

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(16), С. 4560 - 4601

Опубликована: Янв. 1, 2024

This review presents a comprehensive overview of the synthesis cyclopropanes using enantioselective Michael Initiated Ring Closure (MIRC) reactions.

Язык: Английский

Процитировано

4

Reversal of enantioselectivity in cobalt(ii)-catalyzed asymmetric Michael–alkylation reactions: synthesis of spiro-cyclopropane-oxindoles DOI
Jun-Hao Zhang, Weijing Yang, Ning Li

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 4007 - 4013

Опубликована: Янв. 1, 2024

An asymmetric Michael–alkylation reaction with a reversal of enantioselectivity catalyzed by chiral cobalt complexes is reported, giving spiro-cyclopropane-oxindoles complete and controlled switch in stereoselectivity (up to 99% −98% ee).

Язык: Английский

Процитировано

4

Asymmetric Synthesis of Spiro-3,3′-cyclopropyl Oxindoles via Vinylogous Michael Initiated Ring Closure Reaction DOI
Abhijit Manna, Harshit Joshi, Vinod K. Singh

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(24), С. 16755 - 16766

Опубликована: Дек. 5, 2022

A novel organocatalytic cascade approach for the synthesis of spiro-cyclopropyl oxindole derivatives has been developed. The methodology is based on asymmetric vinylogous Michael addition 4-nitroisoxazole to N-Boc isatylidene malonates followed by intramolecular alkylation. Its remarkable stereocontrol, wide substrate scope, and scalability highlight this new developed strategy. Moreover, work represents first example initiated ring closure (MIRC) reaction chiral 3,3′-cyclopropyl oxindole.

Язык: Английский

Процитировано

13

Diverse synthesis of functionalized hydroquinoline derivatives from α-aryl vinylsulfonium salts DOI
Zhen‐Hua Wang, Tong Zhang,

Qing-Fei Yan

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(17), С. 4256 - 4262

Опубликована: Янв. 1, 2023

We achieved diverse transformations of α-aryl vinylsulfonium salts under mild reaction conditions, affording various 1,2-dihydroquinoline and ring-fused tetrahydroquinoline skeletons in moderate to excellent isolated yields.

Язык: Английский

Процитировано

8

Palladium/copper-cocatalyzed three-component tandem cyclization of o-alkenyl arylisocyanides, sulfur ylides with alcohols: direct synthesis of spiro 3,3’-cyclopropyl oxindoles DOI
Yue Gong,

Xue-Cen Xu,

Zixuan Yang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(12), С. 3369 - 3375

Опубликована: Янв. 1, 2024

A novel palladium/copper-cocatalyzed tandem cyclization of o -alkenyl arylisocyanides and sulfur ylides with alcohols has been developed, providing a simple efficient method for the synthesis spiro 3,3′-cyclopropyl oxindoles in single step.

Язык: Английский

Процитировано

2

Synthesis of Bisspiro(oxindole)s by DMAP‐Catalyzed [3+2] Annulation of Isatin‐Derived Morita‐Baylis‐Hillman Carbonates DOI

Xiaohao Wang,

Xingfu Wei,

Yongqiang Xu

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(28)

Опубликована: Май 27, 2024

Abstract A straightforward [3+2] annulation method for synthesizing bisspiro(oxindole) derivatives has been developed by using isatin‐derived Morita‐Baylis‐Hillman carbonates and p ‐quinone methides ( ‐QMs) with 4‐dimethylaminopyridine (DMAP) as the catalyst. The optimized protocol in dichloromethane (DCM) solvent achieves good yields (up to 87 %) diastereoselectivity (>20 : 1). versatility of is shown through synthesis various derivatives, including chiral variants up 82 % ee. intermediates were captured HRMS, a plausible reaction pathway was proposed.

Язык: Английский

Процитировано

2

Intramolecular H-Bonds in an Organocatalyst Enabled an Asymmetric Michael/Alkylation Cascade Reaction to Construct Spirooxindoles Incorporating a Densely Substituted Cyclopropane Motif DOI
Na Wang, Xiao Yan,

Zi-Tian Hu

и другие.

Organic Letters, Год журнала: 2022, Номер 24(46), С. 8553 - 8558

Опубликована: Ноя. 15, 2022

A cascade Michael addition/alkylation reaction between 3-chlorooxindoles and α-cyano chalcones catalyzed using a multifunctional quinine-derived aminoindanol-thiourea substance was investigated. series of spirooxindoles incorporating densely substituted cyclopropane motif were efficiently obtained with moderate to excellent diastereo- enantioselectivity further transformed products versatile structural diversity. Density functional theory (DFT) calculations indicated that the tentative intramolecular hydrogen bonds in chiral catalyst crucial for stereocontrol.

Язык: Английский

Процитировано

10

Stereoselective synthesis of spirooxindole scaffold DOI
Prakash K. Warghude, Anindita Bhowmick, Ramakrishna G. Bhat

и другие.

Elsevier eBooks, Год журнала: 2024, Номер unknown, С. 283 - 308

Опубликована: Янв. 1, 2024

Язык: Английский

Процитировано

0

Investigating the Effectiveness of Spirocyclopropane-Oxindole Derivatives on Clinical Isolates of Candida albicans DOI Open Access

Pouria Rafati,

Jalal Jafarzade, Akbar Hoseinnejad

и другие.

hormozgan medical journal, Год журнала: 2024, Номер 28(1), С. 41 - 48

Опубликована: Янв. 1, 2024

Objectives: Given the spread of azole resistance in Candida albicans (C. albicans), searching for new potent compounds, such as spirocyclopropane-oxindole derivatives is important. This study evaluates antifungal susceptibility on clinical isolates C. albicans. Methods: Antifungal 50 to (4a, 4b, and 4c), nystatin, fluconazole were evaluated according Clinical Laboratory Standards Institute (M27-S4) guidelines. The medicinal dilution range fluconazole, nystatin was 0.256 128, 0.128 64, 0.032 16 μg/mL, respectively. minimum inhibitory concentration (MIC) defined that caused at least 50% growth inhibition compared positive control. Statistical analysis performed using SPSS software, version 20. significance level set P≤0.05. Results: There a significant difference between MIC values against comparison MICs 4c) showed derivative 4a had lower MIC50 (8 μg/mL), MIC90 (16 Geometric (G) Mean (10.126) than 4b (MIC50=64, MIC90=128, G Mean=76.638), 4c Mean=60.547). Discussion: effects significantly less fluconazole. Therefore, with structural changes, these compounds will increase.

Язык: Английский

Процитировано

0

Asymmetric Synthesis of Bis-spiro Cyclopropane Skeletons via Bifunctional Phosphonium Salt-catalyzed [2 + 1] Annulation DOI
Xiaojun Yu, Fan Wang, Juan Du

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(23), С. 6666 - 6671

Опубликована: Янв. 1, 2024

A new approach for constructing enantiopure spiroskeletons was developed via bifunctional phosphonium salt-catalyzed [2 + 1] annulation. These novel scaffolds have potential to facilitate the discovery and development of chiral drugs.

Язык: Английский

Процитировано

0