Enantioselective Construction of Tetrahydroquinolin-5-one-Based Spirooxindole Scaffold via an Organocatalytic Asymmetric Multicomponent [3 + 3] Cyclization

Zhu, Qiu-Ning; Zhang, Yuchen; Xu, Mengmeng; Sun, Xiao‐Xue; Yang, Xue; Shi, Feng

doi:10.1021/acs.joc.6b01598

Cited by 66 publications

(16 citation statements)

References 67 publications

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“…This synthetic methodology is an efficient approach for the construction of chiral tetrahydroquinolin‐5‐one‐based spirooxindole frameworks of biological importance. The proposed mechanism for the synthesis of these enantioenriched products is believed to involve a Knoevenagel condensation, enantioselective Michael addition followed by an intramolecular nucleophilic addition [65] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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“…Recently, a chiral cinchona alkaloid catalyzed asymmetric three-component [3+3] annulation of cyclic enaminone, isatin, and malononitrile was developed by Shi. 14 With enaminone 29 and isatylidene malononitrile generated in situ, the reaction proceeded via an enantioselective Michael addition and subsequent intramolecular nucleophilic addition pathway, which afforded a series of tetrahydroquinolin-5-one-based spirooxindole scaffolds 33 in high yields and with excellent enantioselectivities (Scheme 8).…”

Section: Scheme 7 Synthesis Of Functionalized Glutarimides Through Tementioning

confidence: 99%

Organocatalyzed [3+3] Annulations for the Construction of Heterocycles

Zhu¹,

Huang

2020

Synthesis

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Six-membered heterocyclic systems are widely distributed in many natural products and pharmaceuticals, and the construction of highly functionalized six-membered heterocyclic compounds is an important topic in modern organic synthesis. Organocatalyzed [3+3] annulations represents an important method for assembling a substantial variety of six-membered cycles that contain one or more heteroatoms. This review describes the development of organocatalyzed [3+3] annulations for the synthesis of six-membered heterocycles, including organocatalysis using secondary amines, tertiary amines, phosphines, chiral phosphoric acids and N-heterocyclic carbenes.1 Introduction2 Secondary Amine Catalyzed [3+3] Annulations2.1 Synthesis of Nitrogen Heterocycles2.2 Synthesis of Oxygen Heterocycles2.3 Synthesis of Sulfur Heterocycles3 Tertiary Amine Catalyzed [3+3] Annulations3.1 Catalysis through Multiple Hydrogen-Bonding Interactions3.2 Catalysis of Tertiary Amines as Lewis Bases4 Phosphine-Catalyzed [3+3] Annulations4.1 Synthesis of Nitrogen Heterocycles4.2 Synthesis of Oxygen Heterocycles4.3 Synthesis of Heterocycles Containing Two or More Heteroatoms5 Chiral Phosphoric Acid Catalyzed [3+3] Annulations5.1 Synthesis of Nitrogen Heterocycles5.2 Synthesis of Heterocycles Containing Two or More Heteroatoms6 N-Heterocyclic Carbene Catalyzed [3+3] Annulations6.1 Synthesis of Nitrogen Heterocycles6.2 Synthesis of Oxygen Heterocycles6.3 Synthesis of Heterocycles Containing Two or More Heteroatoms7 Conclusion and Outlook

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“…In addition, different pathways for the construction of spirooxindole nuclei using isatin have been reported. [ 17–19 ] Because of these important biological and pharmaceutical activities for spirooxindole compounds, a great deal of attention has been devoted to the preparation of these compounds and has encouraged scientists to develop biologically active analogs that can be more effective and selective than natural products. [ 20 ] Different homogeneous and heterogeneous catalytic systems have been developed to produce spirooxindole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Mg‐catalyzed one‐pot preparation of benzimidazoles and spirooxindoles by an immobilized chlorophyll b on magnetic nanoparticles

Shamaei

Mahmoudi

Kazemnejadi

et al. 2020

Applied Organom Chemis

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Chlorophyll b was extracted from Heliotropium europaeum plant, then immobilized on magnetic nanoparticles (Fe3O4@SiO2@Chl‐Mg) and found as an efficient and green catalyst for the preparation of a variety of benzimidazoles and spirooxindoles in mild conditions. The catalyst was fully characterized by Fourier‐transform infrared (FTIR), ultraviolet–visible (UV–vis) spectroscopy, X‐ray diffraction (XRD), energy‐dispersive X‐ray spectroscopy (EDX), thermogravimetric (TGA), vibrating sample magnetometer (VSM), transmission electron microscopy (TEM), and dynamic light scattering (DLS) analyses. To prove the catalytic influence of Mg over the reactions, the catalytic activity of the demetalated chlorophyll b as well as some other control experiments was investigated. High to excellent yields were achieved for all entries, whether benzimidazole or spirooxindole derivatives at short reaction times. The catalyst could be recovered and reused for several consecutive runs by a simple external magnetic field without any considerable reactivity loss. The properties of the recovered catalyst were investigated by various analyses. Finally, the reasonable mechanisms were proposed for the reactions based on the literature.

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Enantioselective Construction of Tetrahydroquinolin-5-one-Based Spirooxindole Scaffold via an Organocatalytic Asymmetric Multicomponent [3 + 3] Cyclization

Cited by 66 publications

References 67 publications

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Organocatalyzed [3+3] Annulations for the Construction of Heterocycles

Mg‐catalyzed one‐pot preparation of benzimidazoles and spirooxindoles by an immobilized chlorophyll b on magnetic nanoparticles

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