Synthesis and Crystal Structure of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate

doi:10.1007/S10870-011-0015-9

Paper

Synthesis and Crystal Structure of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate

Published Feb 13, 2011 · A. Sambyal, R. Bamezai, T. K. Razdan

Journal of Chemical Crystallography

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Abstract

The title compound, (2S,6R), Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (C32H30N2O2), was synthesised by the reaction of benzaldehyde, aniline and ethylacetoacetate, in the presence of l (−) proline–Fe(III) complex, formed in situ, at room temperature. The compound was characterized by spectral methods and X-ray diffraction studies. The compound crystallizes in the triclinic space group P − 1 with the following unit-cell parameters: a = 9.651(4), b = 10.909(5), c = 13.737(7) Å, α = 106.597(7), β = 108.664(8), γ = 99.779(6)°, Z = 2. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at 100 K and refined by full-matrix least-squares procedures to a final R-value of 0.0633 for 3415 observed reflections. The 1,2,5,6-tetrahydropyridine ring exhibits a flat boat conformation. The structure has intra- and intermolecular hydrogen bonds of the type N–H···O, C–H···O and C–H···π, which help to stabilize the crystal structure.Graphical AbstractCrystal structure analysis of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate.

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The crystal structure of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate reveals a flat boat conformation and intra- and intermolecular hydrogen bonds, aid

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis and Crystal Structure of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate

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References

New piperidinyl- and 1,2,3,6-tetrahydropyridinyl-pyrimidine derivatives as selective 5-HT1A receptor agonists with highly potent anti-ischemic effects.

The new compounds show promising neuroprotective effects by selectively binding to 5-HT1A receptors, with promising neuroprotective activity in a transient middle cerebral artery occlusion model.

Synthesis and biological characterization of 1-methyl-1,2,5,6-tetrahydropyridyl-1,2,5-thiadiazole derivatives as muscarinic agonists for the treatment of neurological disorders.

Muscarinic agonists show potential in treating neurological disorders like Alzheimer's disease, schizophrenia, chronic pain, and drug abuse.

An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines.

This study presents a phosphine-catalyzed [4 + 2] annulation method for the synthesis of highly functionalized tetrahydropyridines with excellent yields and regioselectivity.

Highly enantioenriched tetrahydropyridines from chiral organosilanes: application to the synthesis of quinolizidine alkaloid (-)-217A.

This study presents a novel method for preparing enantioenriched tetrahydropyridines with high diastereoselectivity, enabling the rapid total synthesis of (-)-quinolizidine 217A.

Asymmetric syntheses of new functionalized beta-amino alcohols via diastereoselective addition of organometallic reagents onto oxazolidines.

Diastereoselective reactions between organometallic reagents and oxazolidines produce chiral beta-amino alcohols with vinyl, alkynylsilane, and allyl or allenylsilane functions.

Design, synthesis, and biological characterization of bivalent 1-methyl-1,2,5,6-tetrahydropyridyl-1,2,5-thiadiazole derivatives as selective muscarinic agonists.

Bivalent muscarinic agonists show high affinity and strong agonist activity, potentially benefiting neurological disorders like Alzheimer's disease, schizophrenia, and chronic pain.

Dramatic change of regioselectivity in the addition of silylated organolithium reagents with oxazolidines induced by the presence of a titanium salt

Incorporating titanium salt into diastereoselective reactions between oxazolidines and organolithium reagents significantly changes regioselectivity, leading to allyl and allenylsilane derivatives.

Citations

Ultrasound Promoted One-Pot Multicomponent Synthesis of Highly Functionalized Tetrahydropyridine Derivatives

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Aluminized polyborate is an efficient, reusable catalyst for solvent-free synthesis of alkyl 1,2,6-trisubstituted-4-[(hetero)arylamino]-1,2,5,6-tetrahydropyridine-3-carboxylates, offering cost

Synthesis of tetrahydropyridines by one-pot multicomponent reaction using nano-sphere silica sulfuric acid

Nano-sphere silica sulfuric acid (NS-SSA) effectively synthesizes 1,2,3,4-tetrahydropyridines in one-pot multicomponent reactions, offering convenience, nontoxicity, and high yields.

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