125593-06-8

Upstream product

• 591-50-4 iodobenzene 
• 56475-87-7 3,4-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 114523-69-2 1-methoxycarbonyl-2-methoxy-1,2,5,6-tetrahydropyridine 
• 1796-27-6 piperidine-1-carboxylic acid methyl ester 
• 113718-34-6 β-bromo-α-methoxy-N-(methoxycarbonyl)piperidine 

Relevant academic research and scientific papers

REGIOSELECTIVE INTRODUCTION OF ALKYL GROUPS TO THE POSITION α OR γ TO NITROGEN ATOM OF PIPERIDINE SKELETONS USING ANODIC OXIDATION IN A KEY STEP

β,γ-Unsaturated N-alkoxycarbonyl-α-methoxypiperidines, which were prepared from N-alkoxypiperidines by using anodic oxidation in a key step, were regioselectively alkylated at the α-position by using Grignard reagents in the presence of BF3*Et2O, whereas in the presence of CuBr, the alkylation took place at the γ-position.

Regioselective Palladium-Catalyzed Tandem α-Arylation/Isomerization of Cyclic Enamides

Palladium-catalyzed reactions of aryl iodides with the cyclic enamides 1-(methoxycarbonyl)-1,4,5,6-tetrahydropyridine (1), 1-formyl-1,4,5,6-tetrahydropyridine (2), and 1-formyl-2-pyrroline (3) result in regioselective α-arylation, with concomitant isomerization of the double bond into conjugation with the nitrogen atom.The new enamides 1-(methoxycarbonyl)-2-aryl-1,2,3,4-tetrahydropyridines (4), 1-formyl-2-aryl-1,2,3,4-tetrahydropyridines (5), and 1-formyl-5-phenyl-2-pyrroline (6a) were isolated in various yields.The migration of the double bond is affected (a) by an amino group in the ortho position of the aryl iodide; (b) by the presence of silver salts; and (c) partly by a 4-methyl group in the tetrahydropyridine ring.In these cases the allylic compounds 2-aryl-1,2,5,6-tetrahydropyridines (10a,b and 13) are formed.