107134-95-2

Upstream product

• 110-86-1 pyridine 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 63581-32-8 3-<(4-methylphenyl)methylene>amino-2-pyridineamine 
• 70008-27-4 1,2,6-trimethyl-4-p-tolyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 146763-34-0 diethyl 1-(4-methoxyphenyl)-2,6-dimethyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 154220-97-0 1,2,3,4-tetrahydro-2-(4-methylphenyl)quinazoline 
• 82408-01-3 3,3-dimethyl-2,3,4,5,10,11-hexahydro-11-[(4-methyl)phenyl]-1H-dibenzo[b,e][1,4]diazepin-1-one 
• 107134-96-3 N-<(triphenylphosphonio)(4-methylphenyl)methyl>-pyridinium dichloride 
• 99618-04-9 N-p'-methylbenzylidene-o-phenylenediamine 
• 120-03-6 2-(p-tolyl)-1H-benzimidazole 
• 7118-65-2 5-chloro-2-(p-tolyl)-1H-benzo[d]imidazole 
• 36422-59-0 diethyl 4-(4-methylphenyl)-2,6-dimethyl-1,4-dihydropyridin-3,5-dicarboxylate 
• 113700-20-2 N-pyridinium betaine 

Relevant academic research and scientific papers

Synthesis of thiazolidine-4-carboxylic acids and N-(1-sulfonatoalkyl)pyridinium betaines from N-(1-chloroalkyl)pyrydinium chlorides

N-(1-chloroalkyl)pyridinium chlorides (1) react with L-cysteine to yield thiazolidine A-carboxylic acids.When salts 1 are not isolated, N-(1-sulfonatoalkyl)pyridinium betaines can be obtained under particular conditions.

AN EXPEDIENT ROUTE TO 1H-BENZIMIDAZOLES AND 1H-IMIDAZOPYRIDINES

1H-Benzimidazoles, 1H-imidazopyridines, and 1H-imidazopyridines can be synthesized readily by reaction of unisolated N-(1-chloroalkyl)pyridinium chlorides with 1,2-benzenediamines, 2,3-pyridinediamine, and 3,4-pyridinediamine, respectively.

A new and convenient method for the preparation of 2-substituted quinazolines

Aldehydes, converted in situ into N-(1-chloroalkyl)pyridinium chlorides using thionyl chloride and pyridine, react with 2-aminobenzylamine, under mild conditions, to yield 1,2,3,4-tetrahydroquinazolines. The latter can be aromatized readily by treatment w

Novel syntheses of heterocycles with N-(1-haloalkyl)azinium halides. Part 2. Preparation of N-unsubstituted 1,4-dihydropyridines

N-(1-Chloroalkyl)pyridinium chlorides, prepared from thionyl chloride, pyridine, and aldehydes, readily react with enaminocarbonyl derivatives to yield 1,4-dihydropyridines under mild and neutral conditions.

Novel synthese of heterocycles with N-(1-haloalkyl)azinium halides. Part 5. Preparation of N-substituted 1,4-dihydropyridines

Thirty N-substituted Hantzsch 1,4-dihydropyridines were prepared under mild and neutral conditions from N-substituted enaminocarbonyl derivatives and aldehydes activated under the form of N-(1-chloroalkyl)pyridinium chlorides by means of thionyl chloride

NOVEL SYNTHESES OF HETEROCYCLES WITH N-(1-HALOALKYL)AZINIUM HALIDES: PART 6. PREPARATION OF 2,3,4,5,10,11-HEXAHYDRO-1H-DIBENZODIAZEPIN-1-ONES

Conversion of aldehydes into N-(1-chloroalkyl)pyridinium chlorides (by means of pyridine and thionyl chloride) and further reaction with 3-(2-aminophenyl)amino-5,5-dimethyl-2-cyclohexenone provide a novel and efficient route to the title compounds.

N-(1-HALOGENOALKYL)HETEROARYLIUMSALZE - SYNTHESE UND REAKTIONEN

The first synthesis of the title compounds 4 is described.These salts are products of a chemoselective three component reaction (eq. 1).By means of various nucleophiles, compounds 4 are transformed into the substituted products 6 (eq. 2).

Anomer Controlled Substitution Reactions with Some N-Alkylpyridinium Compounds

The results of semiempirical MNDO calculations on bond lengths, heats of formation, and net atomic charges of compounds 6, 7, and 8, which all contain an N-alkylpyridinium moiety (see Table 1), allow general trends to be recognized.These trends allow the prediction of important reactivity characteristics of this series of compounds and were the reason for the synthesis of compounds 9, 24, and 26 and for tests of their usefulness.Specifically, the C1-N2 bond length serves as a useful criterion for the reactivity with nucleophilic partners, especially in combination with thermodynamic data calculated from reactions (3) and (4) (Tables 3 and 4).In 7 and 8, this bond is very long as a consequence of an extreme anomeric effect.This observation is reflected in the (experimentally tested) property of the complexes 9 to split off the pyridine moiety.The Cl atom in 6a does not influence the C1-N2 bond length but it does activate the C1 atom toward nucleophilic attack and can itself function as the leaving group . - A remarkable example, both on the basis of the MNDO results (using the model compound 6i) and from the experimental viewpoint, was observed for the class of compounds 24a: The calculated C1-N2 bond length of 6i (1.563 Angstroem) could be classified as adequate for nucleophilic substitution of the pyridine moiety controlled by the anomeric effect on the basis of experimental tests.Whereas "normal" N-alkylpyridinium salts (e.g. the N-methylpyridinium cation, 6b) are hardly ever attacked in the C1 position, the preparative usefulness of this structural element can now be considerably increased by use of the anomeric effect.This is demonstrated by the synthesis of compounds 5, 9h, 17, and 22 from 9, 25a and 25b from 24a as well as 27a from 26a.