35488-10-9

Upstream product

• 540-23-8 p-toluidine hydrochloride 
• 5421-92-1 1-(4-pyridyl)pyridinium chloride hydrochloride 
• 1412913-70-2 5-methyl-1-(4-pyridyl)-1H-1,2,3-benzotriazole 
• 64858-67-9 1-(4-methylphenyl)-1H-1,2,3-triazolo[4,5-c]pyridine 
• 626-64-2 pyridin-4-ol 
• 5435-54-1 4-hydroxy-3-nitropyridine 
• 13091-23-1 4-chloro-3-nitropyridine 
• 54696-69-4 4-(4-methylphenyl)amino-3-nitropyridine 
• 1412913-71-3 4-methyl-N¹-(pyridin-4-yl)benzene-1,2-diamine 
• 1038315-36-4 3-amino-4-(4-methylphenyl)aminopyridine 
• 106-49-0 p-toluidine 
• 504-24-5 4-aminopyridine 

Downstream Products

• 1412913-72-4 4-(4-methyl-2,6-dinitrophenyl)aminopyridine 
• 1412913-71-3 4-methyl-N¹-(pyridin-4-yl)benzene-1,2-diamine 

Relevant academic research and scientific papers

Selective Functionalization of Aminoheterocycles by a Pyrylium Salt

The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C?N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C?O, C?N, C?S, or C?SO2R bonds are disclosed herein. In contrast to C?N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional-group tolerance. In addition to small-molecule derivatization, Pyry-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.

Use of the graebe-ullmann reaction in the synthesis of 8-methyl-γ- carboline and isomeric aromatic aza-γ-carbolines

Two variants of the Graebe-Ullmann reaction were used to obtain 8-methyl-5H-pyrido[4,3-b]indole (8-methyl-γ-carboline) and the conditions for this reaction were optimized. The feasibility of using this method was studied for the synthesis of a series of isomeric aromatic aza-γ- carbolines from the corresponding 1-(pyridyl)-1H-1,2,3-triazolo[4,5-c]pyridines under thermal and microwave irradiation conditions.

Synthetic Applications of N-N Linked Heterocycles. Part 15. A Facile Synthesis of 4-Pyridyl(aryl)amines via the Reaction between 4-Chloro-1-pyridiniopyridinium Salts and Aryl Amines

4-Chloro-1-pyridiniopyridinium salts (7) and (8) react with primary and secondary arylamines to give high yields of isolable 4-aryliminium salts (9) and (10).These are readily fragmented into 4-pyridyl(aryl)amines (11) and (12) in excellent yields on treatment with sodium cyanide or sodium salts of sulphonic acids.The method fails with the more basic aliphatic amines, since these apparently attack the 2-position of the chloropyridinium ring giving products resulting from ring-opening.Mechanisms of the reactions are discussed.