27876-19-3

Upstream product

• 536-75-4 4-Ethylpyridine 
• 74-96-4 ethyl bromide 
• 1113-78-6 tri(sec-butyl)borane 
• 1120-87-2 4-bromopyridin 
• 50720-05-3 indolyl acetyl chloride 
• 671795-46-3 sec-butylmagnesium bromide 
• 134305-08-1 2-[2-(2,2-Diethoxy-ethyl)-3-methyl-pentyl]-[1,3]dioxolane 
• 84355-18-0 4-sec-Butyl-1-(tert-butyl-dimethyl-silanyl)-1,4-dihydro-pyridine 
• 82126-19-0 4-s-butyl-1-ethoxycarbonyl-1,4-dihydropyridine 
• 63755-30-6 N-ethoxycarbonylpyridinium chloride 
• 598-30-1 sec.-butyllithium 
• 181219-01-2 4-pyridineboronic acid pinacol ester 
• 135351-41-6 2-(2,2-Diethoxy-ethyl)-2-[1,3]dioxolan-2-ylmethyl-3-methyl-pentanenitrile 
• 135351-37-0 2-(2,2-Diethoxy-ethyl)-3-methyl-pentanenitrile 

Relevant academic research and scientific papers

Synthesis and utility of dihydropyridine boronic esters

When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products.

AN IMPROVED SYNTHESIS OF 4-SUBSTITUTED PYRIDINES FROM NITRILES

4-substituted pyridines have been prepared by a four-step sequence in 23-27percent overall yield from nitriles.

A NOVEL 1,2-ALKYL MIGRATION OF TRIALKYL(4-PYRIDYL)BORATES

The reaction of lithium trialkyl(4-pyridyl)borates with Lewis acids or acylating agents produced 4-alkylpyridines via 1,2-alkyl migration from boron to pyridine ring.

A Convenient Method for the Regioselective Synthesis of 4-Alkyl(aryl)pyridines Using Pyridinium Salts

RCu.BF3 reacted with 1-ethocycarbonylpyridinium chloride at the 4-position with almost complete regioselectivity (>99percent) to afford the corresponding 1,4-dihydropyridine derivatives in high yields (81-94percent).The dihydropyridines were oxidized by oxygen to give 4-alkyl(aryl)pyridines (38-68percent).Grignard reagents also reacted with 1-t-butyldimethylsilylpyridinium triflate with almost complete regioselectivity (>99percent) to afford the corresponding 1,4-dihydropyridines, which were easily oxidized to give 4-substituted pyridines in higher yields than above (58-70percent).

REGIOSELECTIVE SYNTHESIS OF 4-ALKYLPYRIDINES VIA 1,4-DIHYDROPYRIDINE DERIVATIVES FROM PYRIDINE

N-Ethoxycarbonylpyridinium chloride (1) reacted with at 4-position with almost complete regioselectivity (better than 99percent) to afford the corresponding 1,4-dihydropyridine derivatives (2) in high yields (81 ca. 94percent).The dihydropyridines were readily oxidized by oxygen to give 4-alkylpyridines (4:38 ca. 68percent yields).

FACILE SYNTHESIS OF 4-SUBSTITUTED PYRIDINES USING GRIGNARD REAGENTS

N-t-Butyldimethylsilylpyridinium triflate (2) reacted with Grignard reagents at 4-position with almost complete regioselectivity (99percent) to afford the corresponding 1,4-dihydropyridine derivatives (3), which are easily oxidized by oxygen to give 4-substituted pyridines (4: 58-70percent).

Metal chelating ligands

Alkyl substitution at the pyridyl periphery of 1, 3, 5, 7-tetra (2-pyridylimino)-benzodipyrroles provides bis chelating ligands with unexpected increase in organic solubility. The bis-chelating ligands may be used to form organometallic polymers as well as being suitable as dyes and metal ion deactivators. The metal complexes of such bis-chelating ligands may also be used as dyes.