Brønsted Base‐Catalyzed Tandem [2+4] Annulation/Tautomerization/Aromatization Reaction of α‐Alkylidene Succinimides with 5‐Alkenyl Thiazolones

Yuan, Chunhao; Yang, Huimin; Gong, Qi; Luo, Shijian; Gu, Jing; Ge, Yanqing; Guo, Hongchao; Xie, Lei

doi:10.1002/adsc.202100425

Cited by 10 publications

(5 citation statements)

References 54 publications

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“…This mild protocol offered a simplest access for the synthesis of fluorescent properties containing functionalized thiazolo‐pyrones 36 b in excellent yield (Scheme 36). [63] All steric and electronic factors of both reactants including the aliphatic substrates were compatible with this method and gave good to excellent yields. The authors investigated the tandem [2+4] cycloaddition/tautomerization/aromatization mechanism by deuterium‐labelling studies.…”

Section: Synthetic Applicationmentioning

confidence: 84%

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

Nagaraju

Nanda

2022

Asian J Org Chem

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The widespread biological activity and manifestation of multiple reactive centers in itaconimides/α‐alkylidene succinimides have made them as one of the valuable synthetic targets. In this domain, various strategies have been developed to portray the proficiency of these N‐bearing heterocycles. The current review summarizes the biological activity, synthesis, and use of itaconimides/α‐alkylidene succinimide in numerous useful transformations under many reacting environments.

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Section: Synthetic Applicationmentioning

confidence: 84%

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

Nagaraju

Nanda

2022

Asian J Org Chem

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“…When 1 a was mixed with 1.0 equiv. of DABCO in a mixed solvent (CDCl 3 :D 2 O=3:1) and stirred at room temperature for 72 h, [14] The mono, di, and tri‐deuterium‐labeled products d ‐ 1 a ‐ 1 , d ‐ 1 a ‐ 2 , and d ‐ 1 a ‐ 3 were obtained respectively in total 62% yield in which the deuteration was found at the γ‐C position (Scheme 5a). Then 1 a was reacted with 2 a under the optimal conditions with 10 equiv.…”

Section: Resultsmentioning

confidence: 99%

Organocatalytic Vinylogous Michael Addition/Cyclization Cascade of 2‐Alkylidene Indane‐1,3‐diones with Enals: A Regio‐ and Stereocontrolled Diversity‐Oriented Route to Indane‐1,3‐dione Derivatives

Kuan,

Chen,

Lin

et al. 2023

Adv Synth Catal

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A substrate‐dependent, regio‐ and stereo‐controlled diversity‐oriented organocatalytic vinylogous Michael addition/cyclization cascade of 2‐alkylidene indane‐1,3‐diones with enals, using secondary amines as the catalyst have been developed. These present methodologies allow the synthesis of spiroindane‐1,3‐diones, tetrahydrofluoren‐9‐one derivatives, and benzofused oxabicyclo[3.3.1]nonanes in a highly selective manner. Plausible catalytic pathways for the formation of these biologically interesting compounds were proposed. Density functional theory (DFT) calculations have clarified and supported the mechanisms how the organocatalyst is able to activate the enals and 2‐hydroxycinnamaldehydes, directing the C‐C bond forming with the vinylogous dienolates and enabling the synthesis of these interesting indane‐1,3‐diones derivatives.

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“…Notably, because of the existence of electron-withdrawing carbonyl groups, α-alkylidene succinimides can serve as a new class of synthons by ring opening. In 2021, the groups working with Yuan and Guo independently documented the ring-opening reaction of α-alkylidene succinimides, leading to the formation of the corresponding annulation products. Among the previously established methodologies, organocatalysis (OC) stands out as the widely recognized and dependable strategy for the transformation of succinimides.…”

Section: Introductionmentioning

confidence: 99%

Construction of 3,4-Dihydroquinolone Derivatives through Pd-Catalyzed [4+2] Cycloaddition of Vinyl Benzoxazinanones with α-Alkylidene Succinimides

Yu,

Huang,

Chen

et al. 2024

J. Org. Chem.

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The construction of 3,4-dihydroquinolone derivatives has attracted a considerable amount of attention due to their extensive applications in medicinal chemistry. In this study, we present the Pd-catalyzed [4+2] cycloaddition of vinyl benzoxazinanones with α-alkylidene succinimides for the efficient synthesis of 3,4-dihydroquinolones. This approach presents numerous advantages, including the ready availability of starting materials, mild reaction conditions without the use of additional bases, and a wide range of substrates. In particular, all of the desired products can be easily afforded in high yields (≤99%) and excellent diastereoselectivities (>20:1). The practicality and reliability of this strategy were demonstrated by the successful scale-up synthesis and subsequent straightforward synthetic transformations.

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Brønsted Base‐Catalyzed Tandem [2+4] Annulation/Tautomerization/Aromatization Reaction of α‐Alkylidene Succinimides with 5‐Alkenyl Thiazolones

Cited by 10 publications

References 54 publications

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

Organocatalytic Vinylogous Michael Addition/Cyclization Cascade of 2‐Alkylidene Indane‐1,3‐diones with Enals: A Regio‐ and Stereocontrolled Diversity‐Oriented Route to Indane‐1,3‐dione Derivatives

Construction of 3,4-Dihydroquinolone Derivatives through Pd-Catalyzed [4+2] Cycloaddition of Vinyl Benzoxazinanones with α-Alkylidene Succinimides

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