6526-37-0

Upstream product

• 108-99-6 3-Methylpyridine 
• 64-17-5 ethanol 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 67-64-1 acetone 
• 71-43-2 benzene 

Downstream Products

• 51-28-5 2,4-Dinitrophenol 
• 108-99-6 3-Methylpyridine 
• 99989-63-6 5-(2,4-dinitro-anilino)-4-methyl-penta-2,4-dienal 
• 135124-73-1 1-((R)-2-Hydroxy-1-phenyl-ethyl)-3-methyl-pyridinium; chloride 
• 34456-60-5 N-(phenylsulfonylimino)-3-methylpyridinium ylide 
• 80253-73-2 (2E,4E,)-5-(2,4-Dinitrophenylamino)-2-methylpenta-2,4-dienal 
• 109162-95-0 3-methyl-1-phenyl-pyridinium; chloride 

Relevant academic research and scientific papers

5-aminopenta-2,4-dienals: Synthesis, activation towards nucleophiles, molecular modeling and biosynthetic implications in relation to the manzamine alkaloids

Substituted 5-aminopentadienals and glutaconaldehydes are key elements postulated in the biosynthesis of the diverse class of manzamine-type alkaloids. The activation of 5-aminopentadienals into electrophilic iminium salts and their subsequent reactivity

Complex polycyclic lactams from pericyclic cascade reactions of Zincke aldehydes

(Chemical Equation Presented) In the course of a simple mechanistic study on the rearrangement of Zincke aldehydes to Z-α,β,γ,δ- unsaturated amides, a thermally induced pericyclic cascade rearrangement that converts Zincke aldehydes derived from allylic and homoallylic amines into polycyclic lactams was discovered. The key reaction involves an E-Z alkene isomerization, a 6? electrocyclic ring closure, a[1,5]-sigmatropic shift of hydrogen, a 6? electrocyclic ring-opening , and a Diels-Alder cycloaddition, and proceeds with excellent stereoselectivity. The unusual observation that furans and an indole serve as dienophiles in this cascade reaction permitted the synthesis of complex, functional group-rich tri- and tetracyclic lactams. In all cases, the rigid polycyclic products are available in only two steps from pyridinium salts and the allylic or homoallylic secondary amines.

Synthesis of δ-tributylstannyl-α,βγ, δ-unsaturated aldehydes from pyridines

(Equation Presented) Zincke aldehydes, which are readily available from the ring-opening reaction of pyridinium salts, are easily converted into δ-tributylstannyl-α,β,γ,δ-unsaturated aldehydes (stannyldienals) by the action of tributylstannyllithium. This reaction appears to proceed via 1,6-stannyllithium addition/elimination of lithium dialkylamide. Several stannyldienals of significant utility for the synthesis of polyene natural products have been made by this route, which proceeds in modest yields, but is successful on multigram scale using inexpensive reagents. Simple stannylenals and stannylenones are similarly available from the corresponding vinylogous amides.

Microwave-promoted synthesis of chiral pyridinium salts

The synthesis of several chiral pyridinium salts via Zincke's reaction can be easily accomplished by domestic microwave oven irradiation. Yield enhancements, reduction of reaction time, and less racemization were observed under microwave heating when compared to conventional heating in similar conditions.

The Zincke's reaction: A new alternative for the preparation of 1-[2- (3-indol)ethyl]-alkylpyridinium chloride derivatives

The Zincke's salts 3 (a-f) were prepared and used for the synthesis of 1-[(2-(3-indol)-ethyl]alkylpyridinium chloride derivatives 5 (a-f) in high yields.

N.c.a. 11C-labelling of benzenoid compounds in ring positions: Synthesis of 3-nitro-[3-11C]toluene and 4-nitro-[4-11C]toluene and their corresponding toluidines

The paper describes the syntheses of n.c.a. 3-nitro-[3-11C]toluene (3a) and 4-nitro-[4-11C]toluene (3b) by reaction of nitro-[11C]methane (1) with 5-dimethylamino-2(or 3)-methyl-penta-2,4-dienylidene- dimethylammonium tetr

Synthesis of Some N-(Phenylsulfonylamino)-1,2,3,6-tetrahydropyridines as Potential Anti-inflammatory Agents

Several N-(phenylsulfonylamino)-1,2,3,6-tetrahydropyridines were synthesized by substituting a sulfonyl group for the carbonyl group of N-(phenylcarbonylamino)-1,2,3,6-tetrahydropyridines 1 in order to investigate the effect of the substitution on the analgesic and anti-inflammatory activities. Nucleophilic attack of pyridine derivatives 2 on 1-chloro-2,4-dinitrobenzene 3 furnished the pyridinium chlorides 4. Compound 4 and benzenesulfonyl hydrazide 5 were reacted to give the 2,4-dinitroanilino derivatives 6. Hydrolysis of 6 furnished the ylides 7. Sodium borohydride reduction of ylides afforded the tetrahydropyridines 8. Compound 8c was found to be the most active anti-inflammatory agent and was as potent as indomethacin, the reference compound. Compound 8f had the most significant hyperglycemic activity.

Synthesis and pharmacological evaluation of some N- [pyridyl(phenyl)carbonylamino]methyl-1,2,3,6-tetrahydropyridines

Reaction of some plcolines 5 with 1-chloro-2,4-dinitrobenzene (6) in acetone furnished methyl-substituted 2,4-dinitrophenylpyridinium chlorides 7. Further reaction with phenyl(pyridyl)carbonyl hydrazides 8 at room temperature furnished isolable 2,4-dinitr