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Regioselective Synthesis of 4-(2-Oxoalkyl)pyridines via 1,4-Dihydro-pyridine Derivatives Using Silyl Enol Ethers and Pyridinium Salts by Kin-ya Akiba; Yoshihiro Nishihara; Makoto Wada is a Chemistry article available to read on EtoBox.

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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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Author

Kin-ya Akiba; Yoshihiro Nishihara; Makoto Wada

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

1983

Language

EN

Field

Chemistry (Physical Sciences)