e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis

An expedient, flexible and convergent access to selectively protected 1, 5-dicarbonyl compounds. Applications to the synthesis of 2, 6-disubstituted pyridines and …

J Boivin, F Carpentier, R Jrad

Index: Boivin, Jean; Carpentier, Floriane; Jrad, Rafik Synthesis, 2006 , # 10 p. 1664 - 1672

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Citation Number: 5

Abstract

Abstract Intermolecular addition of 2-oxoalkyl radicals generated from the corresponding S- alkyl-O-ethyl dithiocarbonates on vinyl ketals afforded selectively protected 1, 5-dicarbonyl compounds in good yields. These key-intermediates can be converted into a plethora of useful substances. Transformations to pyridines and thiopyridines were given as examples.

2-ethyl-2-(2-tosylethyl)-1,3-dioxolane Structure

2-ethyl-2-(2-to...

~85%

2-Ethyl-2-vinyl-1,3-dioxolane Structure

2-Ethyl-2-vinyl...

1-(4-methoxyphenyl)-5-phenylheptane-1,5-dione Structure

1-(4-methoxyphe...

~93%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

dithiocarbonic acid O-ethyl ester S-[4-(4-methoxyphenyl)-4-oxo-1-(2-phenyl[1,3]dioxolan-2-yl)butyl] ester Structure

dithiocarbonic ...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

2-phenyl-2-vinyl-[1,3]dioxolane Structure

2-phenyl-2-viny...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

3-Chloropropiophenone Structure

3-Chloropropiop...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

O-Ethyl S-[2-(4-methoxyphenyl)-2-oxoethyl] carbonodithioate Structure

O-Ethyl S-[2-(4...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

1-Propanone,3-[(4-methylphenyl)sulfonyl]-1-phenyl- Structure

1-Propanone,3-[...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

N/A Structure

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

PTP inhibitor 1 Structure

PTP inhibitor 1

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

1-(4-methoxyphenyl)-4-(2-phenyl[1,3]dioxolan-2-yl)butan-1-one Structure

1-(4-methoxyphe...

~%

2-(4-methoxyphenyl)-6-phenyl-pyridine Structure

2-(4-methoxyphe...

2,2-dimethyl-6-(2-phenyl-[1,3]dioxolan-2-yl)hexan-3-one Structure

2,2-dimethyl-6-...

~%

2-tert-butyl-6-phenylpyridine Structure

2-tert-butyl-6-...

3-Chloropropiophenone Structure

3-Chloropropiop...

Sodium toluene-4-sulphinate Structure

Sodium toluene-...

~55%

1-Propanone,3-[(4-methylphenyl)sulfonyl]-1-phenyl- Structure

1-Propanone,3-[...

N/A Structure

~%

2-tert-butyl-6-phenylpyridine Structure

2-tert-butyl-6-...