67913-78-4

Upstream product

• 110-89-4 piperidine 
• 88064-66-8 1-cyclohexyl-5,6-dihydro-2,4-diphenylbenzoquinolinium tetrafluoroborate 
• 76017-39-5 1-benzyl-5,6-dihydro-2,4-diphenylbenzoquinolinium trifluoromethanesulphonate 
• 75864-90-3 N-benzyl-5,6-dihydro-2,4-diphenylbenzo quinolinium tetrafluoroborate 

Relevant academic research and scientific papers

Kinetics and Mechanism of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 11. ρ* Plots for the Solvolysis of 1-s-Alkyl-5,6-dihydro-2,4-diphenylbenzoquinolinium Cations.

The ρ* values for (1c-h) for (i) solvolysis in trifluoroacetic acid (-5.7), (ii) for solvolysis in pentanol (-1.2), and (iii) for unimolecular reaction with piperidine in chlorobenzene (-3.1) are discussed with respect to (a) the hypothesis tha

Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate

A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridinesvia t-BuOK/DMSO-promotedC-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of thein situgenerated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available starting materials and the absence of transition-metal catalysts, oxidants and undesirable byproducts. A wide synthetic utility of the developed approach was demonstrated by the synthesis of trisubstituted, tetrasubstituted and fused pyridines.

Method for synthesizing polysubstituted pyridine derivative based on oxime ester and unsaturated ketone under catalysis of ferric salt

The invention belongs to the technical field of organic synthesis, and particularly relates to a method for synthesizing a polysubstituted pyridine derivative based on oxime ester and unsaturated ketone under the catalysis of ferric salt. For the first ti

4-HO-TEMPO-Catalyzed Redox Annulation of Cyclopropanols with Oxime Acetates toward Pyridine Derivatives

A 4-HO-TEMPO-catalyzed redox strategy for the synthesis of pyridines through the annulation of cyclopropanols and oxime acetates has been developed. This protocol features good functional group tolerance and high chemoselectivity and also promises to be efficient for the late-stage functionalization of skeletons of drugs and natural products. Mechanism studies indicate that the reaction involves the in situ generated α,β-unsaturated ketones and imines as the key intermediates, which are derived from cyclopropanols and oxime acetates via a TEMPO/TEMPOH redox cycle, respectively. The pyridine products are formed as a result of annulation of enones with imines followed by TEMPO-catalyzed oxidative aromatization by excess oxime acetates. This method not only realizes the TEMPO-catalyzed redox reaction but also broadens the frontiers for TEMPO in catalysis.

Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines

A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.

Synthesis of unsymmetrical polysubstituted pyridines from β-sulfonylvinylamines via 1-aza-allyl anion intermediates

A modular synthesis of highly functionalized unsymmetrical pyridines has been developed from reacting β-sulfonylvinylamines with α,β-unsaturated systems in the presence of base via the formation of 1-aza-allyl anion intermediates. Georg Thieme Verlag Stut

Microwave-assisted four-component, one-pot condensation reaction: An efficient synthesis of annulated pyridines

A one-pot, effective synthesis of pyridines by a modified Kroehnke procedure is described. Polysubstituted annulated pyridines were synthesized in high yields by four-component, one-pot cyclocondensation reactions of N-phenacylpyridinium bromide, aromatic

A novel and efficient 2,4,6-trisubstituted pyridine ring synthesis via α-benzotriazolyl ketones

Reaction of α-benzotriazolyl ketones with α,β-unsaturated ketones resulted in 2,4,6-triarylpyridines, 2,4-diaryl-5H-indeno[1,2-b]pyridines and 2,4-diaryl-5,6-dihydrobenzo[h]quinolines in good yields.

Kinetics and Mechanisms of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 22. Reactions with Various Nucleophiles and a Study of the Effects of Substrate Concentrations, Traces of Water, ands Nature of the Gegenion on the Rates

First- and second-order rate components for the nucleophilic displacements of a variety of N-(primary alkyl), N-(secondary alkyl), and N-benzyl substituents from mono-, bi-, and tri-cyclic pyridine leaving groups by various nucleophiles are independent of substrate concentration, of the nature of the gegenion, and of traces of water in the solvent.Thus assumptions implicit in the reasoning of earlier papers of this series are confirmed, and the conclusion that these nucleophilic displacements can proceed by five independent mechanistic pathways is strengthened.First-order rate components are invariant with the nature of the nuclephile.Second-order rate components vary with nucleophile nucleophilicity in a way that parallels Menschutkin reactions.Activation enthalpies for first-order components are less negative than those for second-order components, in agreement with previous data.

Kinetics and Mechanisms of Nucleophilic Displacements whit Heterocycles as Leaving Groups. Part 15. Dependence of Mechanism of Solvolysis of Pyridinium Cations on Solvent Character: Evidence from Rates,p* Values, and Product Analysis

p* Values are reported for solvolyses of a series of 1-(s-alkyl)pyridinium cations in 2,2,2-trifluoroethanol or 1,1,1,3,3,3-hexafluoropropan-2-ol as solvents in the absence of nucleophiles.The corresponding reactions with pyridine, piperidine, or morpholine as nucleophile in chloroform, acetonitrile, 2,2,2-trifluoroethanol, or 1,1,1,3,3,3-hexafluoropropan-2-ol are kinetically first-order (independent of nucleophile concentration);these allow p* to be calculated. p* Values correlate with solvent ET values except for pentanol and acetic acid, in which cases they are smaller than expected.Product analysis discloses rearrangement products (derived by hydride shifts) only for solvolysis in non-nucleophilic solvents (trifluoroacetic acid and 1,1,1,3,3,3-hexafluoropropan-2-ol) in the absence of added nucleophilic solvents.The results are interpreted in terms of (a) solvent-assisted solvolysis in nucleophilic solvents, (b) SN1 cleavage of the C-N bond in the rate-determining step both for the unimolecular reactions in the presence of external nucleophiles, and for solvolysis in 2,2,2-trifluoroethanol, and (c) rate-determining ion-molecule pair dissociation for solvolysis in trifluoroacetic acid or 1,1,1,3,3,3-hexafluoropropan-2-ol.