125311-40-2

Upstream product

• 108-48-5 2,6-dimethylpyridine 
• 100-46-9 benzylamine 
• 7703-74-4 2,6-bis-(bromomethyl)pyridine 
• 123705-92-0 2,6-bis[benzylsulfanylmethyl]pyridine 
• 1410785-96-4 2,6-bis[benzylsulfonylmethyl]pyridine 
• 780-21-2 N-(4-chlorobenzylidene)aniline 
• 100-52-7 benzaldehyde 

Downstream Products

• 818377-18-3 Norlobelane 
• 125311-41-3 (E,E)-2,6-bis(2-phenylethenyl)pyridine-1-oxide 
• 116539-72-1 2,6-bis-(4-nitro-trans-styryl)-pyridine 
• 68031-94-7 2,6-bis (2-phenylethyl) pyridine 
• 5302-71-6 1-methyl-2,6-di-trans-styryl-pyridinium; iodide 

Relevant academic research and scientific papers

Crystal structure of 2,6-distyrylpyridine

We have crystallized the 2,6-distyrylpyridine compound from the condensation reaction of the 2,6-dimethylpyridine with benzaldehyde (at 135°C) to obtain a model compound having three rings joined with two double bonds in order to understand the structure of poly(2,6-styrylpyridine) and poly(2,6-pyridinediylvinylene) and their formation mechanism. The X-ray structure shows that the title compound belongs to the trigonal crystal system, space group P32, and with unit cell dimensions a = 15.5637(12) A, c = 5.7852(13) A. From the molecular structure it was clear that the substituents on double bonds were in the trans position, which was in agreement to the IR and 1H NMR results. The molecule is planar and forms stacks in the crystal. The molecular structure of 2,6-distyrylpyridine has two trans double bonds between the rings and therefore it can be in three nonequivalent conformations. The preferred conformation showed by X-ray crystallography can be the result of weak steric interactions between the double bond trans hydrogens and the nearby hydrogens of the phenyl or pyridyl groups. The crystal structure, and IR and 1H NMR results are currently reported.

Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst

We explored the bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation for a cascade olefination reaction with nine different methyl N-heteroarenes, including pyrimidines, pyrazines, pyridines, quinolines, quinoxolines, benzimidazoles, benzoxazoles, benzthiazoles, and triazines. An o-quinone catalyst phd (1,10-phenanthroline-5,6-dione) combined with a Br?nsted acid catalyzed the reaction. N-Heteroaryl stilbenoids were synthesized in high yields and (E)-selectivities under mild conditions using oxygen (1 atm) as the sole oxidant without needing transition-metal salt, ligand, stoichiometric base, or oxidant.

C(sp3)-H functionalization of methyl azaarenes: a calcium-catalyzed facile synthesis of (E)-2-styryl azaarenes and 2-aryl-1,3-bisazaarenes

Alkaline earth (Ca2+) catalyzed sp3 C-H functionalization of methyl azaarenes for the synthesis of biologically important (E)-2-styryl azaarenes, 2-aryl-1,3-bisazaarenes and 3,3-bisazaarenyl indolinones has been described. Initially methyl azaarenes react with aryl aldehydes to give β-hydroxy derivatives, which undergo Ca(II) catalyzed thermodynamic elimination to give the styryl azaarenes in a single step. Similarly it may undergo SN1 reaction to give 2-aryl-1,3-bisazaarenes and 3,3-bisazaarenyl indolinones (if isatin used as the electrophile). This green synthetic methodology enjoys the simple reaction procedures, solvent free conditions, step economy, substrate diversity and high yields of the products in short time.

1,2-dibromotetrachloroethane: An ozone-friendly reagent for the in situ Ramberga-Baecklund rearrangement and its use in the formal synthesis of E-resveratrol

Dibromotetrachloroethane (C2Br2Cl4) is demonstrated as a halogenating reagent for the one-pot conversion of sulfones to alkenes by way of the Ramberga-Baecklund rearrangement. Dibromotetrachloroethane successfully replaces known ozone depleting agents CCl4, CBr2F2 and C2Br 2F4. A formal synthesis of E-resveratrol is demonstrated using C2Br2Cl4.

Defunctionalized lobeline analogues: Structure-activity of novel ligands for the vesicular monoamine transporter

(-)-Lobeline (2R,6S,10S; 1a), an antagonist at nicotinic acetylcholine receptors (nAChRs), inhibits the neurochemical and behavioral effects of methamphetamine and inhibits dopamine transporter (DAT) and vesicular monoamine transporter (VMAT2) function. VMAT2 is a target for the development of treatments for methamphetamine abuse. Structural modification of lobeline affords the defunctionalized analogues meso-transdiene (MTD) and lobelane, which have high potency and selectivity for VMAT2. To establish the structure-activity relationships within this novel class of VMAT2 ligands, specific stereochemical forms of MTD, lobelane, and other structurally related analogues have been synthesized. These compounds have been evaluated for inhibition of [3H]nicotine ([3H]NIC) binding (α4β2* nAChR), [3H]methyllycaconitine ([ 3H]MLA) binding (α7* nAChR), and [3H] dihydrotetrabenazine ([3H]DTBZ) binding (VMAT2). Generally, all of these analogues had lower affinities at α4β2* and α7* nAChRs compared to lobeline, thereby increasing selectivity for VMAT2. The following structural modifications resulted in only modest changes in affinity for VMAT2, affording analogues that were less potent than the lead compound, lobelane: (1) altering the stereochemistry at the C-2 and C-6 positions of the piperidino ring, (2) varying unsaturation in the piperidino C-2 and C-6 substituents, (3) introducing unsaturation into the piperidine ring, (4) ring-opening or eliminating the piperidine ring, and (5) removing the piperidino N-methyl group. Furthermore, incorporating a quaternary ammonium group into defunctionalized lobeline molecules in the cis-series resulted in significant loss of affinity for VMAT2, whereas only a modest change in affinity was obtained in the trans-series. The most potent (Ki = 630 nM) and VMAT2-selective compound evaluated was the N-methyl-2,6-cts- bis(naphthaleneethyl)piperidine analogue 28b (1-NAP-lobelane), in which the phenyl groups of lobelane were replaced with 1-naphthyl moieties. Thus, initial structure-activity relationship studies reveal that the most promising structural changes to the lobeline molecule that lead to enhancement of VMAT2 affinity and selectivity are defunctionalization, affording lobelane and MTD, and replacement of the phenyl rings of lobelane with other aromatic moieties that have a π-extended structure.

CONDENSATION REACTIONS OF 2,4- AND 2,6-DIMETHYLPYRIDINES AND THEIR 1-OXIDES

Using the reactions of 2,4- and 2,6-dimethylpyridine-1-oxides with aromatic and heteroaromatic aldehydes under catalysis with potassium tert-butoxide (E)-aryl- and (E)-heteroarylethenylpyridine-1-oxides IIIa-IIIe, IVa-IVc, Va, Vb respectively, were prepared. 1-Oxides IIIg, IVd, IVe and Vc were obtained from the appropriate pyridine bases by oxidation with peracetic acid.Condensation of 2,4- and 2,6-dimethylpyridines with 3-pyridinecarbaldehyde gives a mixture of bases VIa and VIc, and VIb and VId, respectively.On Claisen condensation of 2,6- or 2,4-dimethylpyridine-1-oxide with diethyl oxalate in the presence of sodium hydride and potassium tert-butoxide lactone XIIa and XIIb is formed in addition to α-keto ester XIa and XIb, respectively.From esters XIa and XIb amides XId and XIe were prepared.

Anil-Synthese. 22 Mitteilung. Ueber die Herstellung von Styryl und Distyryl-Derivaten des Pyridins

2,4-, 2,5- and 2,6-Dimethylpyridines react with anils of aromatic aldehydes in the presence of dimethylformamide and potassium hydroxide to yield the corresponding distyrylpyridines ('anil synthesis').Under the same reaction conditions (4-methylstyryl)pyridines are converted to (stilbenylvinyl)pyridines.Similarly, the Schiff's base derived from pyridine-3-carbaldehyde and chloranile on treatment with methyl- and p-tolyl-substituted aromatic hetericycles gives the corresponding (heteroaryl-styryl)pyridines, whereas with the Schiff's bases derived from pyridine-2= and -4-carbaldehyde side reactions, such as dimerization followed by disproportionation predominate.