Novel Synthesis of trans-4,6-Diaryl-5-nitropiperidin-2-ones via Four-Component Reaction from Substituted Nitrostyrenes, Aromatic Aldehydes, Dimethyl Malonate, and Formamide

Zhou, Zhengquan; Liu, Hui; Sun, Qian; Li, Yun; Yang, Jing; Liu, Juanjuan; Yan, Peiyun; Wang, Cunde

doi:10.1055/s-0032-1317044

Cited by 2 publications

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“…Since there are known methods for obtaining piperidines from cyanoacetic acid derivatives [39][40] and malonates [41][42][43], we decided to take methyl (Z)-2-cyano-3-arylacrylates 2h-k as Michael's acceptors. These reagents were also obtained by the Knoevenagel condensation between aromatic aldehydes and methyl 2-cyanoacetate.…”

Section: Resultsmentioning

confidence: 99%

Highly diastereoselective synthesis of piperidine-2-one-substituted pyridinium salts from pyridinium ylides, aldehydes, Michael acceptors and ammonium acetate

Vinokurov¹,

Iliyasov²,

Karpenko³

et al. 2023

Preprint

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A novel four-component diastereoselective synthesis of pyridinium salts of piperidin-2-ones is reported. The Michael–Mannich cascade was conducted using Michael acceptors, pyridinium ylides, aromatic aldehydes and ammonium acetate in methanol. It is a convenient approach to the synthesis of 1-((3SR,4RS,6SR)-5,5-dicyano-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium halogenides with three stereocenters in 48–84% or 1-((3SR,4RS,5RS,6SR)-5-cyano-5-(methoxycarbonyl)-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium halogenide with four stereocenters in 44–74%. This reaction is highly stereoselective. Only one diastereomer was formed. Ammonium acetate plays a dual role, acting as a base and as a nitrogen source. Structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, IR and mass spectra. The formation of a single diastereomer was confirmed by singe-crystal X-ray diffraction studies.

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Section: Resultsmentioning

confidence: 99%

Highly diastereoselective synthesis of piperidine-2-one-substituted pyridinium salts from pyridinium ylides, aldehydes, Michael acceptors and ammonium acetate

Vinokurov¹,

Iliyasov²,

Karpenko³

et al. 2023

Preprint

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DBU-Promoted Cascade Selective Nucleophilic Addition/C–C Bond Cleavage/Hetero-Diels–Alder Reactions of 2-Amino-4H-chromen-4-ones with β-Nitrostyrenes and/or Aryl Aldehydes: Access to 5H-Chromeno[2,3-b]pyridin-5-ones

et al. 2020

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DBU-promoted cascade selective nucleophilic addition/C–C bond cleavage/hetero-Diels–Alder reactions accompanied by aromatization of substituted 2-amino-4H-chromen-4-ones with substituted β-nitrostyrenes or with the combined substituted β-nitrostyrenes and aromatic aldehydes were developed for the synthesis of 2,4-diaryl-substituted 5H-chromeno[2,3-b]pyridin-5-ones. This procedure provides a highly efficient and facile route to functionalized 5H-chromeno[2,3-b]pyridines from readily available substrates under mild reaction conditions.

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Novel Synthesis of trans-4,6-Diaryl-5-nitropiperidin-2-ones via Four-Component Reaction from Substituted Nitrostyrenes, Aromatic Aldehydes, Dimethyl Malonate, and Formamide

Cited by 2 publications

References 1 publication

Highly diastereoselective synthesis of piperidine-2-one-substituted pyridinium salts from pyridinium ylides, aldehydes, Michael acceptors and ammonium acetate

Highly diastereoselective synthesis of piperidine-2-one-substituted pyridinium salts from pyridinium ylides, aldehydes, Michael acceptors and ammonium acetate

DBU-Promoted Cascade Selective Nucleophilic Addition/C–C Bond Cleavage/Hetero-Diels–Alder Reactions of 2-Amino-4H-chromen-4-ones with β-Nitrostyrenes and/or Aryl Aldehydes: Access to 5H-Chromeno[2,3-b]pyridin-5-ones

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