Diversity-oriented one-pot multicomponent synthesis of chromanone-based 3,3′-pyrrolidinyl-spirooxindoles via a 1,3-dipolar cycloaddition reaction

Yue, Jing; Chen, Shuang; Zuo, Xiong; Liu, Xiong‐Li; Xu, Sheng-Wen

doi:10.1016/j.tetlet.2018.11.075

Cited by 21 publications

(4 citation statements)

References 63 publications

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“…A very similar approach was reported by Yue et al ., but with sarcosine being replaced by proline or thioproline. The library of spirooxindole derivatives (30 examples) was achieved in overall good yields (65‐90 %) [37] …”

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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“…Perhaps this made it possible to carry out this multidirectional synthesis of complex spirooxindoles with several stereocenters, with greater stereoselectivity towards the formation of an endo product (5 : 1 -20 : 1 dr; Scheme 21). [154] The known imine formation reaction by mixing of isatins with primary amines or ammonia in the presence of magnesium sulfate can also be successfully used to create spirocyclic molecules. [155][156][157] The imines, depending on structural factors and reaction conditions, can be used as precursors for generating azamethine ylides from them, capable of reacting with dipolarophiles.…”

Section: Synthetic Approaches To Indolone Spirocycles Through 3-iminomentioning

confidence: 99%

Section: Strategy For Creating a Spirocarbon Center On The Isatin Bacmentioning

confidence: 99%

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the synthesis of spiro-linked heterocycles of the indole, quinoline, benzoxazine, benzothiazine, indenoquinoxaline, pyridopyrimidine, and acridine series. Possible approaches to the synthesis of spirocycles through a sequence of well-known Knoevenagel, Michael reactions, deamination cyclization of 1,2-dicarbonyl, CH-acid compounds, direct cycloaddition of activated olefins to isatins, 3-alkylideneindoles, 2-oxindoles, in situ generated azomethine ylides, indenoquinoxalines are analyzed. Attention is drawn to approaches to the preparation of spiro-fused compounds using reactions of intra-and intermolecular dearomatization of indoles. Recent advances in the synthesis of spiro-linked benzo heterocycles from derivatives of 2-olefin substituted anilines are summarized. The examples of the synthesis of spiro-fused heterocycles by means of metal complexes catalyzed decomposition of diazo compounds are given. Some syntheses of biologically active representatives are shown, as well as the use of transformations of spiroheterocycles in the preparation of other heterocycles.

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“…[1][2][3][4] Diversity-oriented synthesis refers to a kind of forward synthesis that usually uses branching diffusion to focus on the diversity and complexity of compounds with the aim of expanding the compound library from point to face. [5][6][7] Because this synthetic method can use combinatorial chemistry to synthesize similar compounds, the properties and structure-activity relationship of the synthesized compounds can be easily studied. 8 Moreover, it hastens the building of a library of natural products with diverse molecular skeletons, complex structures, and rich chemical properties and facilitates the discovery of more lead compounds.…”

mentioning

confidence: 99%

Density Functional Theory Study of Substituent Effects on the 1,3-Dipolar Cycloaddition Mechanism

Sun

et al. 2020

Preprint

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In this study, we performed density functional theory calculations using the B3LYP, M052X, M062X, and APFD functionals to investigate substituent effects on the mechanism of 1,3-dipolar cycloaddition, a classical and effective method for the synthesis of heterocyclic compounds. The results showed that changing the substituents on the chloroxime compounds affects the energy level of the highest occupied molecular orbital and consequently, the progress of the reaction. Finally, it provided an effective idea for this kind of reaction in the design of organic synthesis and the necessary theoretical basis for revealing the course of this reaction.

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Diversity-oriented one-pot multicomponent synthesis of chromanone-based 3,3′-pyrrolidinyl-spirooxindoles via a 1,3-dipolar cycloaddition reaction

Cited by 21 publications

References 63 publications

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

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

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Density Functional Theory Study of Substituent Effects on the 1,3-Dipolar Cycloaddition Mechanism

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