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Regioselective synthesis of 4-(2-oxoalkyl)pyridines via 1,4-dihydro-pyridine derivatives using silyl enol ethers and pyridinium salts

✍ Scribed by Kin-ya Akiba; Yoshihiro Nishihara; Makoto Wada

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 241 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)88414-2

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✦ Synopsis

Trimethylsilyl enol ethers ( 1 ) reacted with l-ethoxycarbonylpyridinium chloride (2 ) at 4-position with high rezoselectivity to afford l-ethoxycarbonyl-4-( 2-oxoalkyl )-1,4_dihydropyridines

( 2 ) in 42 -8'7% yields. When 2, 2, 2-trichloroethyl chloroformate was employed, yields of the corresponding 1,4_dihydropyridines ( g ) were higher ( 80 -100% yields ). $ and 8 were oxidized by oxygen or AgN03 to give 4-( 2-oxoalkyl )pyridines ( 1, : 30 -65% ).

Considerable efforts have been paid to introduce substituents into 4-position of pyridine regioselectively, and recently successful and easily applicable methods were reported on

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