One-Pot Multicomponent Synthesis of Highly Functionalised Piperidines from Aromatic Aldehydes, Cyanoacetates, Nitromethane and Ammonium Acetate

Liu, Juanjuan; Zhou, Zhengquan; Li, Yan; Ye, Weijian; Yao, Juan; Wang, Cunde

doi:10.3184/174751913x13814236405771

Cited by 5 publications

(1 citation statement)

References 12 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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Fully Diastereoselective Synthesis of Polysubstituted, Functionalized Piperidines and Decahydroquinolines Based on Multicomponent Reactions Catalyzed by Cerium(IV) Ammonium Nitrate

Suryavanshi¹,

Sridharan²,

Maiti³

et al. 2014

Chemistry A European J

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The cerium(IV) ammonium nitrate (CAN)-catalyzed, three-component reaction between primary amines, β-dicarbonyl compounds, and α,β-unsaturated aldehydes in ethanol heated to reflux, constitutes a general, one-pot synthesis of 1,4-dihydropyridines. Their reduction with sodium triacetoxyborohydride furnished piperidine derivatives bearing up to five substituents with full diastereoselectivity in a hitherto inaccessible stereochemical arrangement. The reaction proceeded with no significant loss of enantiomeric purity under mild reduction conditions that are compatible with several functional groups that are normally sensitive to reduction. Octahydroquinolin-5-one derivatives, which were prepared by a modified version of the initial multicomponent reaction, were not suitable substrates for the sodium triacetoxyborohydride mediated reduction, but they were transformed into the corresponding decahydroquinolines, including a precursor of the amphibian alkaloid pumiliotoxin C, by catalytic hydrogenation under a variety of conditions.

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ChemInform Abstract: One‐Pot Multicomponent Synthesis of Highly Functionalized Piperidines from Aromatic Aldehydes, Cyanoacetates, Nitromethane and Ammonium Acetate.

Liu

Zhou

et al. 2014

ChemInform

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One-Pot Multicomponent Synthesis of Highly Functionalized Piperidines from Aromatic Aldehydes, Cyanoacetates, Nitromethane and Ammonium Acetate. -The ratios of the substrates as well as the amount of base play a crucial role in the outcome of the reaction. The structure of the products are confirmed by the X-Ray analysis. -(LIU, J.; ZHOU, Z.; LI, Y.; YE, W.; YAO, J.; WANG*, C.; J. Chem. Res. 37 (2013) 11, 684-689, http://dx.

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One-Pot Multicomponent Synthesis of Highly Functionalised Piperidines from Aromatic Aldehydes, Cyanoacetates, Nitromethane and Ammonium Acetate

Cited by 5 publications

References 12 publications

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

Fully Diastereoselective Synthesis of Polysubstituted, Functionalized Piperidines and Decahydroquinolines Based on Multicomponent Reactions Catalyzed by Cerium(IV) Ammonium Nitrate

ChemInform Abstract: One‐Pot Multicomponent Synthesis of Highly Functionalized Piperidines from Aromatic Aldehydes, Cyanoacetates, Nitromethane and Ammonium Acetate.

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